Mark Moskowitz: Within: What Going to Jail Taught Me About Teshuva

David Bashevkin:
Hello and welcome to the 18Forty podcast, where each month we explore a different topic, balancing modern sensibilities with traditional sensitivities to give you new approaches to timeless Jewish ideas.

I’m your host, David Bashevkin, and this month we’re exploring the topic of teshuvah. Thank you so much to this episode sponsor, The Aleph Institute, which is a non-profit Jewish organization established by the Lubavitcher Rebbe, dedicated to assisting and caring for the well-being of members of specific populations that are isolated from the regular community. U.S. military personnel, prisoners and people institutionalized, or at risk of incarceration due to mental illness or addictions.
Thank you so much to our series sponsor, Daniel and Mira Stokar for their generous sponsorship of the entire teshuvah series. This podcast is part of a larger exploration of those big, juicy Jewish ideas. Be sure to check out 18forty.org. That’s 1-8-F-O-R-T-Y, where you can also find videos, articles, recommended readings, weekly emails.

Especially this month, we have so many new articles dropping online on our teshuvah magazine, which you, again, want to check out on 18forty.org. There is a deeply moving passage of Talmud in Rosh Hashanah on 10b, on yud amud bet, I believe, where the Talmud says that on Rosh Hashanah is the anniversary of the day where Yosef, in the biblical story retold in the book of Genesis, in Sefer Bereishis, where Yosef, after he was locked up in prison, was finally freed.

There’s a moving idea from the Sfas Emes, the great Hasidic leader of Ger, where the Sfas Emessays, in many ways this is the entire process of the Yamim Noraim, of the High Holidays that, each of us in many ways continue this story of Yosef HaTzadik, are locked up in prisons, some of our own making, some that have been made for us. We have this suffocation and constriction in our lives.

It’s specifically through the process of teshuvah and specifically through the process of the Yamim Noraim that we’re able to taste, see some window, some glimmer of redemption in the difficulties of our own lives.

I think, like many people, my first introduction to prison, for those growing up at the same time as me, was watching the movie “Shawshank Redemption.” It’s an incredibly powerful movie.

I remember the first time I watched it, and my parents didn’t let me watch the opening scene, which I think has a bit of sexuality involved, but they did let me watch it even though it was rated R. I think they made me skip two scenes. I’ve probably since seen the entire movie, but it’s an incredible film that really is a reflection on what prison, on what incarceration, can do to a person, on the dehumanization that happens to people who are in the prison system.

I happen to know people personally in my own life who have been to prison. More than the effect that it has on them, because I’ve never really spoken to them directly about it, but I’ve spoken to family members, people who’ve had close family members who have been to prison. The toll that it takes on their entire family is usually very much unspoken. There’s this line in “Shawshank Redemption” that always sticks with me.

Andy Dufresne:
Hope is a good thing, maybe the best of things, and no good thing ever dies.

David Bashevkin:
Thinking back to that Sfas Emes, in many ways I think of Yosef HaTzadik, and we think of the difficulty in that story, of Yosef being locked in prison. We almost separate it from the fact, of the toll that it takes on his family life, his connection to his brothers. It’s really all part of the same story, about somebody’s support system, the very locus of their identity being eroded because there is something in their life causing constriction.

Most of our listeners, I assume, have not been to prison. Most of our listeners probably don’t personally know anybody who has been to prison, but maybe I’m wrong. As I mentioned, I do know people who have been to prison. I know close friends who’ve had family members who have been to prison. I do know, in that story of Yosef HaTzadik, of having an element of constriction within your own life.

I do know personally, what it feels like, to feel like there are elements of your life that feel like a prison, that feel constrained, that feel separated, isolated. That there are things in your life that you, maybe, perhaps put in prison, topics that you don’t want to talk about. Areas of your identity, areas of your sense of self, mistakes that you’ve made that you isolate out from the rest of your life and make sure don’t participate in those kiddush and Shabbos table conversations that we have.

We all have elements, if it’s not our entire life and our physical selves, that are in prison. Part of the teshuvah process, I think, is engaging with the notion of incarceration, of isolation, and figuring out how to find freedom even within those points of isolation. How to redeem ourselves when, maybe if we, not in the totality of our entire selves, find ourselves in prison, which most of us don’t.

How to find freedom for those smaller parts of our lives, those unspoken parts of our identity, those topics that make us feel constricted, isolated, and suffocated. How to find a window of freedom even in those aspects of our lives, to bring redemption, and ultimately return, a teshuvahin the totality of ourselves. That is why I am so excited about the conversation today.
This conversation began rather fortuitously, and I owe a great deal of gratitude to my friend, Rafi Chemel. I am only 40% sure that I am pronouncing his last name correctly. Rafi is a listener to 18Forty.

Going into this topic, which I began preparing, really before the summer, I knew that I wanted to interview somebody who was in prison. Rafi, who is a listener, works with The Aleph Institute. He reached out to me, not knowing that I was preparing this, not knowing what was going on. He said, “Let’s work together. I want to be able to bring the message of The Aleph Institute to 18Forty.”

Aside from being a listener and really a wonderful person, Rafi is really the person who made this happen, who built the connections and oversaw every single detail of this. It’s friends like that that make me so grateful to the listening community of 18Forty.

Rafi introduced me to Mark Moskowitz, who has an incredibly moving story. A story of actual incarceration, a story that was benefited from the work of The Aleph Institute, which is why it is my absolute privilege and pleasure to introduce our teshuvah conversation with Mark Moskowitz.

I am so excited because we have a guest today that, I have always been dreaming of, but really was worried that we wouldn’t be able to have a live conversation with somebody who really could share their experience. It is my privilege to introduce our friend, Mark Moskowitz.

Mark Moskowitz:
Hello, David. Thank you for having me on.

David Bashevkin:
Mark, I’m really, really excited to really speak with you. Maybe we could begin, because this is really a story that in many ways is still unfolding. Maybe you could take us back. You obviously spent time in prison, which we will talk about. Tell me a little bit about what was your life before prison. I’m looking at you now. You look like your pretty average, middle-aged Jew.

You told me you’re … He was bragging, he runs marathons. You don’t look like a hardened criminal to me. What was your life before you were incarcerated?

Mark Moskowitz:
Sure. Well David, I grew up in your typical average secular home, a Reform background. I did have a bar mitzvah, successful father, also a Wall Street finance individual. Everything on the outside looked idyllic. Went to private schools and country clubs and vacations. When I left college, I didn’t have any debt to pay back.

Grew up in a financially stable, nice home, but there was always something missing in my own life that I didn’t really know about. It was something that had plagued me for quite a long time. For me, it was a mystery. I think that I had success in my life, despite some of my failings.

I mean, I had a good upbringing, obviously, but there were things in my life that were missing. It’s all just been amazing part of this journey.

David Bashevkin:
Well, tell me a little bit more. What do you mean that there were things in your life that felt that you were missing? What kind of struggles is that? You rose in a fairly affluent home.

Mark Moskowitz:
Yes.

David Bashevkin:
What could be missing?

Mark Moskowitz:
What was missing was the emotional component of growing up. These were the main lessons that I learned while I was in prison, in Otisville, having emotional support from the people you trust the most, which are your parents.

I know that I had harbored a lot of resentment towards them, feeling that I was neglected emotionally as a child. That what looked great on the outside was more important to them than what was really going on in the inside.

David Bashevkin:
Reputation and-

Mark Moskowitz:
Correct. Yes, exactly.

David Bashevkin:
… that kind of stuff, which I think in a lot of people who have grown up in any affluent community, but I don’t want to cast indictments. I grew up in Long Island, in the Five Towns. Appearances, I remember, growing up … Even now in any affluent upper-class neighborhood, appearances and having it together is 90% of the game.

Mark Moskowitz:
Yeah.

David Bashevkin:
You go on and you start a family and you start to work. You go into finance, also.

Mark Moskowitz:
Sure. Well, to just even back up for a moment there. Also, I found in my life that I wanted to have a connection with my father, more than so my mother. For whatever reason, I haven’t quite figured out yet, but he was the one I wanted to have a connection with.

My father had his own struggles in life that I never really realized until I’ve gotten to the latter part of this journey. He was not the easiest of men. I think from him I learned that I needed to shape who Mark Moskowitz really is to what I believe the other person wanted. I was not my authentic self.

David Bashevkin:
I don’t want to incriminate. God forbid, this isn’t an interview about your father. Just old generation, tough, gritty. I mean-

Mark Moskowitz:
Yeah.

David Bashevkin:
… I think a lot of people from that generation-

Mark Moskowitz:
Distant. Exactly. Yeah. I actually have no blame or anger or anything towards my father. I love him. He’s been gone a few years now, but I look at him in fond, fond memories because I also have forgiven him, which is a huge part of my mission in life now, is to get people to understand the power of forgiveness and to move on from a lot of that pain.

The only reason I bring that part up is because learning to please him and not be authentic shaped all of my decisions going forward. I think that’s a really important part of the story that I don’t want to gloss over. When you asked me about family and everything, going into finance was to please him.

His favorite pastime was golf, so I became a great golfer. I immersed myself in that sport because I wanted to spend time with him. Some of my greatest memories of my father are on the golf course. I am ultimately thankful for that.

David Bashevkin:
What you’re saying is so profound to me, and resonates so much. When appearances, and again, it’s not an indictment on any specific community. It’s a part of the world that we live in, but when they are so operative in the way you fashion yourself, which leads to you wanting that external validation, becoming what we would call, a people pleaser, which doesn’t even mean, people on the street. It can mean your own parents.

You want to make them proud. You want to make sure that they approve of you. What’s often left unattended, and I’m not saying this because I’m seeing it in you, I feel this in my soul. What’s left unattended is cultivating your own sense of self, your own moral compass, your own, “What am I about?” I think nowadays … We didn’t grow up in the time of social media.

Mark Moskowitz:
I’m 53 years old, but at that point it was your grandparents. “You’ve got to marry a Jewish woman. You’ve got to get into a career, lawyer, doctor, finance.”

David Bashevkin:
Sure.

Mark Moskowitz:
It was these things that were ingrained in you from a very young age.

David Bashevkin:
Professional pressure is-

Mark Moskowitz:
Yeah. What I’ve learned, also as I’ve started to study the brain and how it grows, is from birth to seven years old, we’re sponges. We soak everything in, and we don’t have the critical thinking at that point, to discern what really makes sense and what doesn’t.

If you keep getting messages hammered home to you all the time, “You need to change who you are to get love. You can’t get unconditional love. It comes with conditions, or you have to marry the right person, or you have to get into the right career.” That sticks with you after you start to get into your critical thinking period.

I truly believe that my parents only have love for me, and my grandparents only had love for me. I just think that they didn’t understand a lot of what we understand nowadays.

David Bashevkin:
Such a delicate balance. Especially in the Jewish world, the communal expectations, which play an important role, of fashioning who we are. It’s not to discard it and grow up on an island. At the same time, feeling like you’re never able to get in touch with, “What do I want? What would I be?”

I’m curious for you because it resonates so much with me, professional expectations, professional embarrassment. I have a very untraditional career, which for much of my life was a source of deep, deep embarrassment.

Who wants to tell somebody, “So what are you up? I work for a Jewish youth organization.” You don’t get a round of applause after that. Thank God, over the last few years it’s gotten much, much better.

I’m curious, do you ever think, is there an alternative history? The job that, looking back, had it not been Wall Street, that you wish you had gone into.

Mark Moskowitz:
I think we all grow up sometimes with visions of certain things. I actually did become a professional golfer for one year after college.

David Bashevkin:
Nuh-uh.

Mark Moskowitz:
Yeah. I went down to Florida.

David Bashevkin:
You were that good?

Mark Moskowitz:
I was really good. Yes, I was really good.

David Bashevkin:
We just started my son on golf lessons. Maybe you’ll stick around after.

Mark Moskowitz:
Love to watch him swing.

David Bashevkin:
Go to Pagoda and you’ll see him swing. He’s six.

Mark Moskowitz:
Six is great. I started when I was super young, like four or five years old, yes, and I worked very hard at it. The country club that we belonged to, it was just a few minute bike ride away from the house, so I was there quite a bit. I even stopped going to summer camp when I was 13, so I could stay home and play golf.

David Bashevkin:
It was serious. Meaning, when you play with a bunch of middle-aged Jews, you’re the best guy on the course.

Mark Moskowitz:
Even though I don’t play that much anymore, I’m still pretty much, the best guy on the course. Yeah.

David Bashevkin:
Let’s fast forward a little bit, and contextualizing that. In the background, this notion of developing your own sense of self and people-pleasing, which I have no doubt that we’ll come back to.

Take me into your professional life. You go into Wall Street. Wall Street’s a big place. What are you doing? You’re in investing. You’re …

Mark Moskowitz:
I started out an institutional salesman. I worked for Paine Webber and then UBS. Basically, I would call on mutual funds and hedge funds and try to have them buy stocks through us. I was working in the equity markets, the stock market.

David Bashevkin:
You’re making a decent living?

Mark Moskowitz:
Yeah, I’m making a good living. I’m living in the city with some friends after I came back from Florida, and we’re all working on Wall Street in one capacity or the other. So we’re having a good time, hooping it up-

David Bashevkin:
Living that life.

Mark Moskowitz:
Hooping it up, having a good time. Exactly.

David Bashevkin:
When do things start to erode? I’ve always had this question and I hope you don’t mind me bringing up his name. I’m not comparing the order of magnitude, of what you did to Bernie Madoff, but allow me to bring up his name.

Did he go into this to start a massive fraud, or did it start to, he just lost track of … He couldn’t keep pace with his image, and just, he fell so far behind.

Now this is not about psychoanalyzing, or an interview about Bernie Madoff. It’s about you. I’m curious, for you, did it begin as cutting corners, or you woke up one morning and said, “Let’s commit some crime. Let’s do some fraud”? How does it begin?

Mark Moskowitz:
It’s not an easy question to answer. Although I haven’t really delved into the psyche of Bernie Madoff either, to me, there are some parallels, to probably most people that are committing white-collar crimes. I do think it goes back to a lot of having to keep up with your neighbors and having to keep up this image that you’ve built so hard to work for.

I think Madoff on the Street, everyone knew something was going on, but no one really had any idea it was what it was.

David Bashevkin:
You knew his name back then?

Mark Moskowitz:
Yeah, of course. He was head of the NASDAQ. He had a big thing going on. Everyone thought he was doing what’s known as front-running trades.

David Bashevkin:
Sure.

Mark Moskowitz:
Front-running trades, for those who don’t know, is when you see a big order come in, you put your own order in front of it.

David Bashevkin:
Get a little bit cheaper.

Mark Moskowitz:
Yeah. You get a little bit cheaper. Boom, and then you … Because he was hitting the same returns every year. He was hitting 9%, 10%, 11% returns no matter what the market was doing. That’s pretty impossible to do.

David Bashevkin:
Yeah. What about you, Mark?

Mark Moskowitz:
Yeah. Going back to me-

David Bashevkin:
Come to your story.

Mark Moskowitz:
Of course. I got married when I was 28, to a woman who, I would say, on the surface, looked like the perfect person. She was pretty. She came from a good family. She grew up at the same country club I did. Well-educated, and her family had a little more stability than mine. Mine was kind of chaotic. We were fun. We were a boisterous type of family. Her family was a little more …

David Bashevkin:
Button up?

Mark Moskowitz:
Buttoned-up is a good way to put it. Yes, conservative. I think I was looking for something in her family that I wasn’t getting out of mine. On the surface, I think we checked a lot of the right boxes. Of course, Jewish and all the other things.

As we started to grow and build a family together, I felt there was no depth of our connection. There was nothing there, really. I think we just grew apart. Over time, as you have kids and you stay together for the kids and you’re not staying together for the right reasons, little by little you’re feeling the neglect that I was feeling as a child, now I’m feeling it again, from the person who’s supposed to love me unconditionally, no matter what.

The first, gosh, 40-something years of my life, I grew up feeling no unconditional love. Everything had conditions and strings to it. If I wasn’t making a lot of money, we weren’t having a good time as a couple. If I was making a lot of money, everything was great.

As life for me started to spiral, after a couple of tough investment decisions in 2010, 2011, right after a couple of very good years in ’08, ’09, when the market was tough I was actually doing pretty well.

David Bashevkin:
Was there a period where you were knocking it out of the park?

Mark Moskowitz:
Those were big years for me. The years, really from 2002 to middle of 2009, I was really making a lot of money.

David Bashevkin:
Were you living large or just like-

Mark Moskowitz:
Living a-

David Bashevkin:
… a good life?

Mark Moskowitz:
… medium large. I’m living a very good life, but also somewhat grounded, and able to save some money, and put some money away for-

David Bashevkin:
But vacationing.

Mark Moskowitz:
Vacationing and country clubs and nice cars, and putting money away for the kids’ colleges and all those kinds of things. Being somewhat responsible, but also living a very good life.

David Bashevkin:
And legit?

Mark Moskowitz:
Yeah. Oh, fully legit. Yeah. No, fully legit. Really, my crime didn’t really start till 2014. It was really just about two years long in terms of what I was doing wrong.

David Bashevkin:
Let’s get to how things started to fray. You have these good years. You have these relationships that feel very conditional. People who love you, if. If you get into the right college, if you have the right career, if you’re making the right money, right vacations, all this stuff.

There’s a little bit of an emptiness inside. Was the emptiness, you getting in touch with that, is that part of what kicked off the fraud, or when things started to fall apart?

Mark Moskowitz:
I think, as I alluded to when we first started, I think I was successful despite my problems.

David Bashevkin:
Got you.

Mark Moskowitz:
My emotional problems. I think I was a good market. I was in the right place at the right time. I was doing well. I was smart. I was definitely a hardworking person, but I think over time it just gets exhausting to feel like you’re fighting every day.

Imagine, if you will, working really hard, getting up at 5:00 in the morning, taking a 5:30 train into the city, getting to your desk by 7:00, 7:15. Working till 5:30, 6:00, getting home at 7:30 and then just wanting to hang out and talk to your wife a little bit, and she’s busy on the phone.

I’m not blaming any of this on her, but I’m just giving the scenarios of what I interpreted has happened in my life.

David Bashevkin:
Okay.

Mark Moskowitz:
It just gets exhausting, and you want to fight for a marriage, you want to fight for this, but sometimes you just can’t. You just can’t keep doing it. I think for me, after so many years of being in toxic relationships with my parents, toxic relationship with my wife at the time, I think I was just emotionally drained and I was letting my business fail. I was really-

David Bashevkin:
It started to fall apart?

Mark Moskowitz:
It started to fall apart. I had moved my hedge fund into another fund in 2011. That did not do well and I lost a good chunk of money in that, and was starting to rebuild it. Everything just felt like I was just climbing uphill all the time, pushing a boulder uphill all the time.

There was no joy. There was no fun in life. I had stopped playing golf because my kids were getting older now. I didn’t want to go to the golf course and be away from them for six hours on Saturday and Sunday. That’s when I wanted to spend time with them. They were good athletes in their own right, so I was shuttling them around and being what I thought was a good father, because my father didn’t do the same thing for me. Of course, I overcorrected for him.

Now I’m fully immersed in my children’s lives, which I’m still happy I did. I don’t regret any of that.

David Bashevkin:
Sure.

Mark Moskowitz:
I keep using this word, but it’s just exhausting. It’s just so tiring. There’s never a break. There’s never a time where you’re just taking care of your own self. In the last six or seven years, this concept of self-care has become very important. Although I was an athlete and I would run or whatever, I would get up even on the weekends at 4:00 in the morning to run.

It was never really any time for Mark. It was always squeezed in between work and my kids and whatever.

David Bashevkin:
Take me … I’m sorry to get specific, but I do want to hear. Take me to the scene of the first time that, either you cut a corner or you outright committed a crime.

Mark Moskowitz:
Sure.

David Bashevkin:
How does that begin?

Mark Moskowitz:
Sure. Well, cutting a corner … You’re cutting corners all the time on Wall Street because your quarterly performance is everything. Right?

David Bashevkin:
Sure.

Mark Moskowitz:
Are you taking advantage of a piece of information that you hear? That’s pretty common type-

David Bashevkin:
That’s insider trading.

Mark Moskowitz:
Insider trading, yeah. You’re doing things here and there. A lot of it’s overlooked. A lot of it’s not really too big a deal, but it’s a way to make the numbers.

In 2015, my wife and I were starting to separate. Now I’m taking care of two homes. My business has been suffering for a while, so I’ve been using a lot of the cash to take care of living expenses, your normal living.

I moved out. All of a sudden it’s like, there’s just so little cash in the account. Now you’ve got this hedge fund with money in it and you’ve got the ability to borrow from it. It says in my documents that you could borrow from it and pay it back within 90 days. So you take a loan, pay it back, take a loan, pay it back. You just keep paying Peter and Paul.

David Bashevkin:
Yeah, you’re living like-

Mark Moskowitz:
You’re just living like this thing, and then hoping every week, every quarter, you make good numbers and-

David Bashevkin:
To pay it back.

Mark Moskowitz:
To pay it back. Of course, the stress can-

David Bashevkin:
Because you’re borrowing from your clients-

Mark Moskowitz:
You’re borrowing from your investors. Right, you’re borrowing from investors and then you end up putting it back, so on and so forth. Then at some point it just grows and it gets to a point where you can’t really just easily put it back because you just dig too deep a hole.

I think one of the questions you had asked initially was, I don’t really believe that anyone in our situation, we’ll keep it to the white-collar crowd.

David Bashevkin:
Sure.

Mark Moskowitz:
I don’t believe anyone’s going out there and saying, “I am going to steal money from these people.” That was definitely not me. Intent is a big part of our federal system, and I definitely know that I did not intend to do this.

You’re looking at your credit card bills. You’re looking at your mortgages. You’re looking at all these different things and then you’re looking at your account. You’re saying, “Okay, I could take 10,000 or 20,000 or 50,000,” whatever it is.

David Bashevkin:
Tell me the actual crime that you were indicted for.

Mark Moskowitz:
Sure.

David Bashevkin:
What exactly? You’re borrowing and you are paying back. At what point does it get past the point of, “This is risky. This could come crashing down,” to, “Oh, this is a problem”?

Mark Moskowitz:
In late 2015, early 2016, I was starting to get over my head, and I was starting to get the auditors asking me how come I haven’t put the money back in yet. You’re audited, you get audited financials.

I had an audit team that was taking care of all these things. They’re like, “You got to start putting it back, start putting it back.” I was getting close to the 90 days-

David Bashevkin:
You didn’t have the money.

Mark Moskowitz:
I didn’t have, to put it back, right? Exactly. Like I said, taking care of two homes and taking care of all the things. Kids still have to go to camp. The kids still have to do what they got to do.

It was around, just after the first quarter, end of 2016. At that point, I had taken about $600,000, which is in the scheme of Bernie Madoff-

David Bashevkin:
Wall Street-

Mark Moskowitz:
In the Wall Street, it’s really not much, and the total number was about 695,000 I think, was the final tally that they came up with. I was able to keep trading and I was able to keep the thing afloat.

I know that, that was the point where it was all over and done with. Now I was in the mode of the really horrible place, of just trying to hide from everything.

David Bashevkin:
Correct.

Mark Moskowitz:
Getting the mail before it gets to the house, and doing whatever you can to just figure out a way to hide this from people. Hoping that you can make one trade, and maybe make it all back.

David Bashevkin:
When you’re playing from behind, you play from desperation. The risk compounds because now you’re taking risks, not that makes sense, but the risk to cover this differential that you need to do.

Mark Moskowitz:
Of course.

David Bashevkin:
I assume the trades get riskier and the hole gets deeper.

Mark Moskowitz:
Yeah. Yes. The answer is yes. The trades got riskier, but I was able to not be a total addict. I was able to keep it somewhat in check. I wasn’t going to like, “Okay, I’m going to blow the five million here on one shot, on black or red.” There was some level of coherence going on there.

David Bashevkin:
At this point-

Mark Moskowitz:
It’s the most desperate time in your life. You see it all crumbling. Look, intellectually speaking, you know that you’re done. You’re just praying.

David Bashevkin:
You knew it. You knew it.

Mark Moskowitz:
You know that you’re done. All the lies-

David Bashevkin:
You’re separated from your wife, you’re living alone.

Mark Moskowitz:
Yeah.

David Bashevkin:
How are you getting sleep at night? What are you doing to get to sleep at night?

Mark Moskowitz:
I will say, thank God-

David Bashevkin:
You’re having a drink. You’re watching television.

Mark Moskowitz:
Thank God I’m not a drinker, and I never did turn to alcohol to any greater degree than just a cocktail every now and then. I did turn to sweets. I was probably eating Dunkin’ Donuts twice a day or something, but that was my drug of choice-

David Bashevkin:
A little binge eating.

Mark Moskowitz:
… with sugar. A little binge eating.

David Bashevkin:
That’s a real thing.

Mark Moskowitz:
Oh, for sure. Oh, my gosh. It’s the same part of the brain. It’s the same part of the brain that alcohol triggers.

David Bashevkin:
You’re in an apartment now?

Mark Moskowitz:
Yeah. I’m living in an apartment. My kids are coming over every now and then, but not that much. I’m really doing the minimum to be existing in the world. I’m not completely a hermit, but I’m really just-

David Bashevkin:
That’s a heartbreaking language, the minimum to be existing in the world.

Mark Moskowitz:
Yeah.

David Bashevkin:
It’s genuinely heartbreaking. I don’t know why I got a little emotional just hearing you say that. I’ve definitely had times in my life, where it’s like when you take those stress naps, you just … Again, I’m afraid to use the words. It’s almost like experiential suicide.

I don’t want to, God forbid, take my own life, but I don’t want to be alive either. You just want to be, “I don’t want to be here.” Obviously, things are dark and things are negative.

At this point, what are you guilty of? You’re guilty of, you haven’t paid back. You’re taking money from your clients, not paying it back.

Mark Moskowitz:
Correct.

David Bashevkin:
Is that enough right there? Meaning, is that a fine, that’s prison time? In your head, when this catches up to you, what do you think is going to happen?

Mark Moskowitz:
Sure. I often talk about when I’m giving speeches and when I’m talking to people, is the worst lies that we tell are the ones we tell ourselves because we have nobody to keep us in check at that point. We’re just lying to ourselves.
The idea of being able to pay it back and the idea of that, those were all lies that I kept telling myself, and that it’ll all be okay. To your question, did I really think at the time that I was guilty of a crime? No, I was doing something that I needed to do, to keep my family going.

I was justifying it in that sense, which is no justification at all. It’s terrible. Going back to what we were talking about before, not being able to be authentic, not being able to have trust in people. Again, this all stems back to those early days of my life.
When you don’t have it in your DNA to be authentic and to feel like you can get love unconditionally, you hide, you build up a wall of distrust, which is something that, if you have children out there, people that are listening, get your kids to believe in, that you can give them unconditional love. It’s the most important thing in the world.

I didn’t feel I had anybody in the world that I could talk to. I felt so alone and I felt like I didn’t know … I was at my wits end and I did contemplate the idea of taking my own life.

David Bashevkin:
You did?

Mark Moskowitz:
Yeah. Never anything, I think, too seriously, but “Hey, you know what? I could just turn into that oncoming tractor trailer going 80 miles an hour and it’ll all be over.”

David Bashevkin:
God forbid.

Mark Moskowitz:
Yeah. I, thank goodness, did not do that.

David Bashevkin:
Coming back to the story, at what point do you realize, “There are people who are now looking into me. I am now going to be under investigation”?

Mark Moskowitz:
I did not know anything until Yom Kippur of 2016.

David Bashevkin:
Meaning, you’re hiding.

Mark Moskowitz:
Yeah. I’m hiding. I was planning on going to shul that day, but I am really, like I said, taken myself out of society.

David Bashevkin:
You’re like, “You know what? I’m going to go to shul on Yom Kippur.”

Mark Moskowitz:
Yeah. I was doing what I could do to stay in the world. The minimum I could do, as I said. All of a sudden, I get a knock at the door.

David Bashevkin:
On Yom Kippur?

Mark Moskowitz:
On Yom Kippur.

David Bashevkin:
In the morning?

Mark Moskowitz:
In the morning, yeah. Before I go to temple. Yeah.

David Bashevkin:
You were ready to go?

Mark Moskowitz:
Yeah. It was 8:00 in the morning. I’m ready to go. I had dinner the night before, and all ready to fast and do what I have to do. It’s like, who could it possibly be? Who’s knocking on my door?

David Bashevkin:
Yom Kippur morning.

Mark Moskowitz:
Yeah. My kids are with my wife and I’m just, whatever. Who is it? It’s the FBI. I clenched for a second there. I’m like, “Oh.”

David Bashevkin:
Did you know right away what this was about?

Mark Moskowitz:
Yeah. Yes, I did. I did. I opened the door and they told me that I was a target of an investigation. They handed me a card of the prosecutor. They handed me their cards and they said, “Have your attorney call the prosecutor. Do you have any questions?”
I think I still, maybe had a little bit of anger and arrogance. Well, I definitely had a lot of anger, but I guess, maybe I was still a little bit arrogant. I fired back at them. “You do realize this is the most holy day for a Jewish person.”

Their answer was, “Well, we could have come down here with three or four SUVs, sirens blaring and arrested you on the spot, so you should be thankful for that.” And that was really humbling. Like, whoa, okay, this is real now.

David Bashevkin:
Meaning, initially it’s like, “How dare you inconvenience me on my Yom Kippur.”

Mark Moskowitz:
Exactly. Right, exactly. Like, “What are you doing?” Like it’s-

David Bashevkin:
In retrospect, you should never commit a crime, but if you’re going to get arrested or you’re going to be faced with this, it’s kind of Yom Kippur appropriate in a way. So they leave and now you got to figure out what you’re going to do.

Mark Moskowitz:
They leave, and I decide to continue on with what I was going to do for the day.

David Bashevkin:
You went to shul.

Mark Moskowitz:
I went to shul.

David Bashevkin:
You’re kidding me.

Mark Moskowitz:
No. And at this point in time, I wasn’t going to the shul that we were members of. I was going to go to the Chabad near me, so I decided to just go. And of course, as I was there, I’m just filled with rage and anger and disappointment and-

David Bashevkin:
Rage at who?

Mark Moskowitz:
Everybody really. I was angry with everybody. I didn’t take any responsibility for myself. It’s my parents. It’s my ex, it’s the FBI agent that came to me, it’s my investors. Honestly, I was just angry. And I feel like I was angry for a long time in my life. And I feel like it was one of the things that really was a poison for me was that anger and hatred. I was angry at God. I’m like, how could God put me in this position? Here I am trying, I’m here in temple trying to repent for my sins. And I would never have classified myself as an observant Jew prior to that, other than a little bit here and there. But I was angry with God. Why me? Of all the people who are doing stuff in the world, why me? Why am I the one who’s got to bear the brunt of this?

David Bashevkin:
So after this process, it’s remarkable to me that you carried on and went to shul, almost like a cathartic experience, like a place to… prayer through rage, through anger, which is a real thing. What are the next steps now? There’s a court case. Do you have to plead? What happens next between you and actually being incarcerated?

Mark Moskowitz:
I have to say that there were some fortunate things in my life going on, even during this time. Number one was, I wasn’t arrested on the spot, so my case was sealed. So nobody knew about any of this, which I didn’t really know until a couple of weeks later, so my case was sealed. The second thing that was fortunate was is, it went very quickly. Sometimes, what they call the time of pretrial, which is what’s known as the time from when you’re arrested to the time that you actually either surrender or whatever, for some people it could take years, and that’s depressing. For me, it was about 11 months. It was, I think late September, early October of ’16, and I surrendered in September of 2017.

David Bashevkin:
Say it again. This is Yom Kippur, 20-

Mark Moskowitz:
’16.

David Bashevkin:
And you?

Mark Moskowitz:
I surrendered September of 2017.

David Bashevkin:
Meaning, surrendered to-

Mark Moskowitz:
To Otis. To prison, to actual prison.

David Bashevkin:
Okay. We’ll get there.

Mark Moskowitz:
Yeah. So basically I got myself a lawyer. We called the prosecutor, now this is probably a month forward. We had a couple of just precursor motions in front of the judge, but nothing too serious.

David Bashevkin:
Is your mindset right now with the lawyer, I’m innocent, let’s fight this?

Mark Moskowitz:
No, so that’s actually a great point. I should have brought that up is, the first time I went to meet with the lawyer he’s like, “All right, well tell me the story. Tell me what happened.” And the first thing I said to him was, “I’m guilty. Just make the best deal we can.” And he was taken aback by that. I guess people don’t usually come out and say that. But I knew I did something wrong. I knew I wasn’t blame free. I knew I did something wrong. I knew I hurt people. That’s the bottom line is, I hurt people. So I’m like, “Just make the best deal you can possibly make.”

So then in early November we had a meeting with the prosecutor and his team, and this was what they call their show and tell, where they bring you into their office and they put on this big dog and pony show about the evidence that they have against you. And it was me and my attorney, and there was probably 10 people on the other side of the table. Boxes stacked high, with what I guess they had. But I don’t-

David Bashevkin:
Did it require that much evidence? Are they wire-

Mark Moskowitz:
No.

David Bashevkin:
… tapping your phone?

Mark Moskowitz:
No, I think-

David Bashevkin:
-wire transfers?

Mark Moskowitz:
… a lot of it was just for show. Honestly, I kept thinking to myself, these boxes are probably empty, there’s nothing in them.

David Bashevkin:
They just want to let you know that we mean business.

Mark Moskowitz:
Exactly. So they go over this whole thing. They make this whole big deal. Meanwhile, the whole time I’m sitting there like, “I’ll go in tonight if you make me a good deal.” That was my mindset.

David Bashevkin:
Did you know that you were facing prison time or were you hoping that maybe, get a fine? And in your head, I feel like-

Mark Moskowitz:
In my head, I did not think I was going to prison. Up until the day I got sentenced in July, I did not think I was going to prison. I thought I would do probation at home, or like you said, pay a fine or do something. I mean, I did something wrong, but it wasn’t a violent crime. I didn’t think I needed to be removed from society type of crime. So in my head, I’m thinking, just make the best deal you can. And we’ll-

David Bashevkin:
Pick it up from there.

Mark Moskowitz:
… pick it up from there.

David Bashevkin:
I just want to mention, the length that you say that it went quickly is really powerful. I actually have, not one, I have two very close friends of mine who have very close family members who spend time in prison. And one of them once talked to me about the experience and he says, “The most difficult period is that waiting period where you don’t know what’s going to happen, where the whole sentence, everything’s hanging in the balance.” Once you know what the problem is, once you know the object of your anxiety, it’s manageable. But in that whole waiting period, you don’t even know what to be anxious for exactly.

Mark Moskowitz:
Yeah, that’s a great point. And the fact that it went fast for me was a blessing. Another blessing was, because my case was sealed, there was really no crime at that point, so I was able to apply to drive for Uber and Lyft. And they have a criminal background check, but when they did it, there was no criminal background at all.

David Bashevkin:
Wait Mark, what was your title? You were a hedge fund manager?

Mark Moskowitz:
I was general partner of my hedge fund.

David Bashevkin:
General partner of a hedge fund. But in order to make ends meet during this period, you started driving for Uber and Lyft?

Mark Moskowitz:
Yeah.

David Bashevkin:
What else are you going to do that-

Mark Moskowitz:
Well, it turned out to be twofold. I mean, one was, there’s some income involved with it, but for me, I mean I had enough couple of bucks to keep myself floating for the next few months. But for me it was really getting out of the house. And that was what you were just talking, that’s why you prompted me when you were talking about your friends, of your people that you knew, because that’s a depressing time. Being alone in your home, just either drinking, if that’s what your thing is or whatever it is. For me, driving was a blessing. I could get out. I could get out, I’m a very personable person, so I’m happy to talk. I was driving a Mercedes, so everybody was excited that they were getting picked up in a Mercedes.

David Bashevkin:
Because it was your car.

Mark Moskowitz:
It was my car. Yeah. I owned my car. So everyone was excited about that.

David Bashevkin:
Being on the other side, I mean, that’s the first time where you’re the one ordering the Ubers. I feel the veneer, which we began with of appearances and reputation, the hardest part is admitting that now I’m on the other side of this. The hardest part to me is not having your hedge fund fall apart, but it’s announcing to the world that I’m no longer on that side of the table. I’m now the one picking you up, not the one being picked up. Was that-

Mark Moskowitz:
I think a mindset that I’ve always had in my life, which I guess was a big blessing, David, is that, I often would just see what the problem was ahead of me and then just figured out a way to solve it, which I think I lost in that two year period. I was hiding from my problems instead of just facing them head on. I was hoping they would go away or that I could make them go away. Once the fund was shut down, once I had no way to make money, once I was just sitting in my apartment alone, I was like, all right, I’ll just go on the app and see if they approved me. I didn’t really think they were going to approve me to drive.

David Bashevkin:
I actually think that’s an act of deep bravery. I really do. Thank God, I’ve never been in this situation. But I think the part, because I am also, identify so much as being this appearance driven people, the hardest part, it’s almost like it’s not losing your job, but looking for another job… And you saying, “Look, I got to make ends meet.” And I assume the conversations during that period must have been … Did you tell people what was going on, because they’re a stranger, or no?

Mark Moskowitz:
No, no, because I was afraid that they would … I know that Lyft and Uber have strict policies, so I had to keep that very quiet. So part of my veneer was, I’m just retired and just doing this for fun.

David Bashevkin:
That’s what you would tell your friends?

Mark Moskowitz:
That’s what I would tell people. Yeah. No, not my friends, that’s what I would tell people driving.

David Bashevkin:
What were your friends thinking? Did they know that you were an Uber driver?

Mark Moskowitz:
I don’t even know if anybody knew. I wasn’t telling anybody and I wasn’t really seeing anybody. Like I said, I was really just keeping to myself.

David Bashevkin:
Okay. So you’re driving Uber, you’re driving Lyft.

Mark Moskowitz:
Yes.

David Bashevkin:
And then July you get sentenced.

Mark Moskowitz:
So, of March of 2017, it all becomes public. I plead guilty in open court at that point. So going back to the part in November, when we met with the show and tell, basically they give you a piece of paper. And on that piece of paper says the deals that they’re willing to make with you.

David Bashevkin:
Gotcha. What, there are options?

Mark Moskowitz:
So the longer you wait, the worse the deal gets.

David Bashevkin:
Gotcha.

Mark Moskowitz:
They’re expedient. They want expediency.

David Bashevkin:
We’ve got to close this up.

Mark Moskowitz:
Exactly.

David Bashevkin:
We’ve got to move on, we don’t need this guy.

Mark Moskowitz:
Yeah, exactly. I need my promotion after I bag this guy kind of thing.

David Bashevkin:
Yeah.

Mark Moskowitz:
So it was, the first deal was 28 to 33 months in prison. And then if you waited after a certain time, they would go up. I don’t know exactly.

David Bashevkin:
Waited to plea.

Mark Moskowitz:
Yeah, exactly.

David Bashevkin:
Or go to trial. Then-

Mark Moskowitz:
If we go to trial, then there’s no deal.

David Bashevkin:
And what were you facing if you went to trial?

Mark Moskowitz:
Well, part of the problem with the system is, in theory I was facing 18 to 20 years. Probably closer to six to eight years if I had really been found guilty. But when you’re thinking about life and eight or 10 or 12 years, as opposed to two and a half years, it’s a big difference. You’re looking at a decade. So it’s not a very fair system in that regard. They sort of force you to plead guilty. Most people do. I mean, most people who get caught end up pleading guilty. I mean the government has a 97% win rate. Nobody has that.

David Bashevkin:
You don’t want to go up against the government.

Mark Moskowitz:
You do not want to go up against the government.

David Bashevkin:
The good batting average.

Mark Moskowitz:
They’re going to figure it out. They’ll twist your family’s arm if they have to. They’ll twist whatever they have to, to kind of get you to plead out.

David Bashevkin:
So you decided on the spot in there, I’m going to take the-

Mark Moskowitz:
Well, I knew I would take the deal, but there was no benefit to saying that right away. So I think we had six weeks or so, right after the New Year or something like that, so then it was just about hammering out the deal. Now the interesting thing with the deal is, if the judge who was going to sentence me went above the guidelines, which was 28 … So if she went above 33 months, then I have the right to appeal the decision. If she goes below the 28th, then the government has-

David Bashevkin:
They can appeal.

Mark Moskowitz:
Then they can appeal. Exactly.

David Bashevkin:
Interesting.

Mark Moskowitz:
Yeah. Now they say that the judges are very impartial and that the judges are pooled, and they just, it’s luck of the draw. But I really got a terrible judge, I got a terrible judge. I got someone who was appointed by Bill Clinton. She was definitely more on the left side, very favorable to blue collar crime.

David Bashevkin:
Uh-huh. But tough on-

Mark Moskowitz:
But tough on white collar, looks at white collar people as entitled and spoiled, and perhaps that’s what I was, for sure. So I agreed to plead guilty, and I pled guilty in March. So now it came out publicly, now it came out in the papers and wherever it came out.

David Bashevkin:
Was there a report on it in the press?

Mark Moskowitz:
Yeah. Yeah.

David Bashevkin:
Okay.

Mark Moskowitz:
So now the phone calls come in and the embarrassment starts and all that stuff actually comes out.

David Bashevkin:
Which phone call were you dreading the most?

Mark Moskowitz:
From my parents, from my parents.

David Bashevkin:
They were alive.

Mark Moskowitz:
Yeah. Yeah. They were both alive at the time.

David Bashevkin:
What was that phone call like?

Mark Moskowitz:
It was just difficult. It was hard because I didn’t really know why I was in that situation.

David Bashevkin:
What do you mean?

Mark Moskowitz:
At that point, I knew the crime I committed, but when you’re intelligent and you feel like life should be good, you still don’t know why you’re there.

David Bashevkin:
It feels like, why is the universe stacked against me?

Mark Moskowitz:
Yeah. And this is what ends up, when we get to it, this is what makes the story so great, is I had suffered for so long in my life, forgetting the whole crime part. My whole life, first half of my life was all about suffering. I was never really happy. I might’ve been happy on the outside.

David Bashevkin:
But it’s a subtle kind of suffering because somebody … And pardon me for pushing back on this, you grew up, your material wellbeing was all taken care of and you grew up in an affluent home. It was an internal, quiet type of suffering that you can’t even complain about, honestly. Do you hear what I’m saying?

Mark Moskowitz:
I do. And I actually I’ll tell you that I-

David Bashevkin:
It’s those problems that no one takes seriously, even though suffering is such an internal experience that regardless of what’s causing it, if you feel bereft in the inside of your soul, you’re bereft, regardless of whether or not you belong to a country club.

Mark Moskowitz:
Right. Whether you drive up in a Mercedes or a Pinto, you’re still miserable, right?

David Bashevkin:
Yeah.

Mark Moskowitz:
So, and believe me, I’ve struggled with even that guilt. Why should I be miserable? I have everything that a person could possibly want. What right do I have to feel this emotional distress?

David Bashevkin:
Did you start unpacking this when your parents call, or just a quick-

Mark Moskowitz:
It was a quick, “I’m sorry. I don’t know how it happened. I apologize. I’ll figure it out.” And they were like, “Okay.” They were fine. They weren’t fine, but they understood that it is what it is.

David Bashevkin:
Did they follow it up or did they-

Mark Moskowitz:
They were supportive.

David Bashevkin:
Okay.

Mark Moskowitz:
They were probably the most supportive as they’ve ever been in my life, which is interesting. It’s ironic.

David Bashevkin:
Which phone call was the most painful, that didn’t go the way that you were hoping?

Mark Moskowitz:
I had some investors who were friends of mine, not friends from town, but just, they became friends over time, and having to actually discuss it with them and tell them how difficult it was, that was really tough because I really felt that I betrayed them. I felt like I betrayed everybody, my family, my friends, everyone, but the people who I really ended up taking money from, they probably have it the worst. And-

David Bashevkin:
Allow me to ask, and I’m happy to take you in if you don’t want to talk about it, how did your children react?

Mark Moskowitz:
I don’t really know how they reacted at the time, because I ended up becoming estranged from them at that point.

David Bashevkin:
Because of what was-

Mark Moskowitz:
Because of this, because I was just told through third-party sources to not try to reach out to them. But I know I’m sure it was difficult on them. I know it’s difficult on them because a couple of them, two of my younger kids I don’t really have much of a relationship with at this point, but we’re working on it. We talk a little bit every now and then. And then my older child, he and I have a good relationship and we’ve been working on some things and he’s been very forgiving and understanding of what happened and he’s mature. He’s grown up himself.

David Bashevkin:
Sure. It’s hard for a kid. I mean you-

Mark Moskowitz:
So it’s difficult, your whole world is taken. Look, we were in the middle of getting divorced, so that was already tough. I mean, my kids were young. They were 15, 13 and 11, so they were young. They were old enough to understand and young enough to not have any control over it.

David Bashevkin:
So you go eventually to the sentencing. It’s probably the next part.

Mark Moskowitz:
So sentencing is July 27th.

David Bashevkin:
Who do you bring to your sentencing? Are you allowed to bring friends?

Mark Moskowitz:
Yeah. I ended up bringing … My parents came and a couple of friends, and my sister came.

David Bashevkin:
You invited some friends?

Mark Moskowitz:
Yeah.

David Bashevkin:
Just as support?

Mark Moskowitz:
And people who had written letters for me on my behalf, which was a nice thing to do. Part of the procedural process that you go through is, you have to complete what’s known as a pre-sentencing report, PSR.

David Bashevkin:
Okay.

Mark Moskowitz:
They actually complete the PSR, the Feds do. And then they send it to you and then you have to see if there’s any mistakes on it.

David Bashevkin:
What’s on there? What’s the kind of stuff is on a PSR?

Mark Moskowitz:
First off, it’s your occupation, your education, your social security number, all these different little things.

David Bashevkin:
It’s like figuring out, the same thing you go to a doctor’s office, it’s-

Mark Moskowitz:
Yeah. Kind of that, exactly.

David Bashevkin:
Okay.

Mark Moskowitz:
But mine had 13 mistakes on it.

David Bashevkin:
Really?

Mark Moskowitz:
Yeah. It said that I had had a wrong address, said that I had a commercial driver’s license that was suspended and then revoked, which I never had a CDL, so… And a couple things with education and just some stuff that just didn’t make sense to me. So I marked it up, sent it back to my attorney. Said, “You got to get these things corrected,” and they never got corrected. So when my judge sentenced me, I think she already had an implicit bias against people who are in the white collar world. And she was looking at a faulty report, and she even referenced the CDL as how sloppy I was in my life. I think that hurt me in the sentencing. She had no love for me at all, that’s for sure, so.

And one of the things, which I guess, as the person who is being sentenced, you’d like to know there’s a little bit of compassion in the system. And maybe before you’re going to take someone’s life in your hands, in terms of being the judge, would it have killed you to maybe have a 20 minute conversation with me to find out who I really am? You’re reading a report with erroneous information on it and then you’re making a decision based on that. And my ex-wife had put some stuff on the report that wasn’t kind, which wasn’t true either, so there was a lot of stuff in there. And you give up your day in court, when you plead guilty. You give up your right to … But it doesn’t mean you’re inhuman, it doesn’t mean you don’t have the right to at least correct some wrongs.

David Bashevkin:
How long’s the whole motion?

Mark Moskowitz:
The whole sentencing thing is less than an hour. There’s some procedural stuff that you-

David Bashevkin:
But that’s when you find out how long-

Mark Moskowitz:
That’s when you find out how long you’re going in for, and she gave me the max, she gave me 33 months.

David Bashevkin:
Which is? Just do the numbers for me. That’s two and a half years?

Mark Moskowitz:
It’s three years. So 36 months would be three years. So yeah, it’s two years and some change.

David Bashevkin:
When she said that, and said 33 months, your reaction was relief, anger, rage, sadness?

Mark Moskowitz:
Well remember at that point, like you had asked, I kind of thought that maybe I was just going to get probation.

David Bashevkin:
So you were also taken aback, you were surprised?

Mark Moskowitz:
Yeah, of course. And I got up, I read a letter that I’d written just apologizing to my victims and really being complicit.

David Bashevkin:
Do you have that letter still?

Mark Moskowitz:
No, I don’t think I do.

David Bashevkin:
Okay.

Mark Moskowitz:
But it was essentially, I know that I screwed up, and I take responsibility for everything.

David Bashevkin:
Were you proud of what you wrote in that letter? Do you think it holds up?

Mark Moskowitz:
That’s a great question. I think what I wrote was, again, being a people pleaser, I think I wrote what I thought they would want to hear. And one of the things which I do think about a lot is that I was so broken. I was so broken at the time in really every sense of the word. I was physically broken. I was emotionally broken. I was financially broken. I was spiritually broken. And then I’m taking all of this, all of my past, into my current day. I’m only doing the only thing I know how to do is survive, and that is to tell someone what I think they want to hear. I think if I could have gone back with everything I know now if I could have gone back and told the judge probably what was really in my heart, which I didn’t probably even know at the time what was in my heart, because it was so deep buried in everything. So it was just-

David Bashevkin:
What was that? I mean, finish it.

Mark Moskowitz:
That I was just really sad. I know my life looked like this charmed life, but it wasn’t, and it was not an easy life. It was a difficult life. It was one that you wish you could get a do-over sometimes, and I know I can. That’s why I’m trying to make the most out of it that I can now. I haven’t really ever thought about what I would say to her at this point. But I think I would want her to know that I felt that I struggled a lot with emotional neglect and that it was an overarching theme of my life.

David Bashevkin:
You were always playing catch up. You were always trying to-

Mark Moskowitz:
Yeah. I was always trying to figure it out.

David Bashevkin:
Let me ask you, so what’s next? They sentence you for 33 months. Do you go directly to prison?

Mark Moskowitz:
No. So the next step is you go home, basically just live your life.

David Bashevkin:
Go back home?

Mark Moskowitz:
Yeah, you go back home. Well, so I was-

David Bashevkin:
It’s like you’re going to shul after you get-

Mark Moskowitz:
Yeah, exactly. So I guess it’s a good time to say, I wasn’t remanded. So there’s a difference between being out on bond. I was out on no bond.

David Bashevkin:
They weren’t worried that you were going to run.

Mark Moskowitz:
They weren’t worried that I was going to run, and I wasn’t remanded. So some people get remanded to a county facility where you’re doing time served. I was not remanded. I was able to live in my apartment. I was able to be home this whole time. Sometime in middle August I get-

David Bashevkin:
Do you have to wear a bracelet?

Mark Moskowitz:
Nope. Nothing. You could run if you want, but-

David Bashevkin:
You have to check in with somebody?

Mark Moskowitz:
You have to check in with prob … Well, yes.

David Bashevkin:
Daily?

Mark Moskowitz:
No, once a week.

David Bashevkin:
And what’s the check in? You have to go to the actual office or?

Mark Moskowitz:
Yeah, you have to go to the office at Newark.

David Bashevkin:
Can’t just text, call them?

Mark Moskowitz:
No.

David Bashevkin:
Can’t text him.

Mark Moskowitz:
No, no, no. No, you can’t just text them, “Hey, I’m here. I’m around still. Don’t worry about me.” No. It’s, you had to legitimately go in there. They drug tested you every time.

David Bashevkin:
Okay.

Mark Moskowitz:
So yes.

David Bashevkin:
And how long is this period between the sentencing and-

Mark Moskowitz:
Actually no, when you’re on pretrial, you’re always visiting probation. That’s part of what you do.

David Bashevkin:
No, I’m saying, after the sentencing to prison, how long is that period? You went home after.

Mark Moskowitz:
So yeah, sentencing was July 27th. I surrendered to Otisville September 7th.

David Bashevkin:
You had a summer?

Mark Moskowitz:
I had a summer, yeah.

David Bashevkin:
What’s in your head that summer? Are there preparations you make before going to prison? Are there things-

Mark Moskowitz:
Yeah. You get rid of your stuff. I sold my car, moved some of my possessions to my parents’ house.

David Bashevkin:
Why do you have to get rid of your possessions, because you-

Mark Moskowitz:
You don’t have to, but I didn’t have any place to store them. I didn’t own a home. I was living in an apartment that I wasn’t going to be able to continue to pay rent for, that kind of thing. So you just kind of-

David Bashevkin:
Is it hard to break a lease? Is there a rule that allows you to break a lease if you’re going to be in prison?

Mark Moskowitz:
No. So I just stopped paying.

David Bashevkin:
Gotcha.

Mark Moskowitz:
I just stopped. I didn’t have a choice, so they took my security deposit, which I would expect that they did and they ding your credit. That’s all, pretty simple stuff. So you’re just basically getting your affairs in order. You’re just trying to get everything in order.

David Bashevkin:
So just stripping down to the essentials.

Mark Moskowitz:
Just stripping down to the essentials, exactly.

David Bashevkin:
You don’t think of that, because you’re living by yourself. You don’t have a place to keep your stuff. You have to start selling your life. Did you sell stuff on eBay? You’re selling-

Mark Moskowitz:
I mean, I just sold it wherever I could. I didn’t have that much stuff to get rid of.

David Bashevkin:
Okay.

Mark Moskowitz:
I had-

David Bashevkin:
You weren’t a stuff, like tchotchkes-

Mark Moskowitz:
No, I didn’t have a lot of thing. I was more of a, let’s say, an experience person. But my mother took some stuff. My sister took some stuff.

David Bashevkin:
Your siblings stuck with you through this?

Mark Moskowitz:
Yeah they did. They did.

David Bashevkin:
So you finally surrender. Where do you go to surrender to prison? I feel like it’s finding one of those Peter Pan bus lines or a Greyhound bus. It’s always like, “Meet us on the corner of 36 and 3rd,” or whatever. And you’re like, “I’m never going to find” … Where do you go?

Mark Moskowitz:
Before that though, I got my sentencing letter, what day I’m supposed to surrender and where. And I was originally designated to Lewisburg facility. Now I was also designated to a camp level, so when you get sentenced, you get points. You can get zero to 10. Zero is, you’re in a camp. One or two points, you’re in a camp. 10 is, you’re in a penitentiary, the worst place you could be.

David Bashevkin:
Do they literally call it a camp?

Mark Moskowitz:
Yeah, yeah.

David Bashevkin:
Okay.

Mark Moskowitz:
It’s called FPC. Federal prison camp.

David Bashevkin:
Okay.

Mark Moskowitz:
So I was originally designated to Lewisburg, and through only I could say the grace of God, I ended up getting in touch with Aleph. I reached out to a rabbi, Rabbi Berel Paltiel, and he wanted to try to get me into Otisville because that was a place where a lot of the Jewish people would go.

David Bashevkin:
How did you find out about Aleph?

Mark Moskowitz:
From someone who had gone to prison prior to me and had called me and reached out to me, out of the blue.

David Bashevkin:
And then reached out to prior, and just said, “Hey, this is someone.”

Mark Moskowitz:
Yeah. “Hey, you shouldn’t go to Lewisburg. You got to go here. So call these guys up.” So the rabbi said, “Look, I’m happy to try to get you in, but I need a reason.” And at that time my father had been suffering with cancer and Lewisburg was a six hour drive as opposed to Otisville, which was a two hour drive. So they ended up getting me into Otisville.

David Bashevkin:
Why is Otisville better than Lewisburg?

Mark Moskowitz:
Well, number one, it is closer, just 90 miles north of New York City. But, it’s just one of those places, especially for Jewish people, where there’s a shul with books and-

David Bashevkin:
Yeah, I want to hear about that experience. We’ll definitely get to that in a second.

Mark Moskowitz:
Yeah, for sure.

David Bashevkin:
You get the switch to-

Mark Moskowitz:
To Otisville.

David Bashevkin:
To Otisville.

Mark Moskowitz:
Right.

David Bashevkin:
Tell me what happens next now, how do you check in to prison? What did that seem like?

Mark Moskowitz:
So, my parents drive me up and there’s three facilities in Otisville. You have the camp, where I am. Then you also have the medium facility, which is, medium’s a pretty high level. You’ve got a lot of sex offenders there and you have a lot of gang dropouts. There’s a real fence around the medium. The camp is low security. And then there’s another unit for people who are in witness protection.

David Bashevkin:
Okay. Oh really?

Mark Moskowitz:
Yeah. And you can’t see them. They’re really hidden behind there. According to the guards, there were Al-Qaeda and mafia people there who are all going to testify on behalf of the government. So you got to surrender to the medium, but no one tells you that. So I got my paper, my parents drive me up. They tell you to come up with no possessions. They’re going to take anything you have, they’re going to throw it away. So don’t come up with any possession. So I’m just wearing-

David Bashevkin:
Pants and a shirt.

Mark Moskowitz:
… shorts that are ripped and old sneakers and a T-shirt. So we go to the camp to surrender and there’s no one there to tell me where to go. So all of a sudden, I see what looked like an inmate, guy covered in tattoos. I’m like, wow, this doesn’t look like the place I thought I was going to be going to. And he tells me, no, you got to go over there to that facility and got to check in there.

David Bashevkin:
One of the inmates helped you out.

Mark Moskowitz:
Yeah. One of the inmates helped me out, this guy Aaron, who ended up being a good friend of mine. So I ended up going to the medium facility. That looks like real hardened, like a bad place to be, like bad things happen to you in there. So my parents and I walk in. This CO, corrections officer comes out, gets me, tells me to say goodbye to my parents and takes me into processing.

David Bashevkin:
Is that an emotional goodbye? Or it’s like-

Mark Moskowitz:
The CO was really nice, I have to say. He was a pretty cool guy. He’s like, “Don’t worry.” He’s like, tell my parents, “Don’t worry about it. He’s going to be fine. It’ll be gone before you know it.” It kind of really eased the tension. And I said to my parents, I said, “I don’t know what’s going on in my head, but I’m going to figure it out.”

David Bashevkin:
That’s what you told your parents.

Mark Moskowitz:
Yeah.

David Bashevkin:
“I don’t know what’s going on in my head, but I’m going to figure it out in prison.”

Mark Moskowitz:
I was very motivated to make changes, really motivated. And that was the right mindset to go in with because a lot of people go in there with this mindset of blaming everybody else. At that point I was still angry. I was still upset. I was still all the emotions that I was feeling, but I was also like, figure it out.

David Bashevkin:
Let’s use this time, let’s figure this out.

Mark Moskowitz:
Let’s use this time. Exactly. So they take you down to the bottom. They check you in, they strip search you. They make you turn and cough and make sure you don’t have drugs in your system.

David Bashevkin:
They really do that, like “Shawshank Redemption” stuff?

Mark Moskowitz:
Yeah. Oh yeah. Yeah. I mean they don’t-

David Bashevkin:
They don’t hose you down?

Mark Moskowitz:
They don’t hose you down, no. But they make you squat and cough, see if anything comes at your-

David Bashevkin:
Really?

Mark Moskowitz:
Yeah. Make sure you’re not holding any drugs. They drug test you. A lot of guys show up to prison, drunk and high, it’s amazing.

David Bashevkin:
Really?

Mark Moskowitz:
Yeah. And I never knew that.

David Bashevkin:
And what happens if you’re drunk and high?

Mark Moskowitz:
They throw you in the hole until you sober you up.

David Bashevkin:
The hole?

Mark Moskowitz:
The solitary confinement.

David Bashevkin:
For real, that’s-

Mark Moskowitz:
Yeah, for real. Oh yeah. And a lot of guys show up that way. It’s amazing.

David Bashevkin:
But they really strip search you totally down?

Mark Moskowitz:
They really strip search you. Then they give you-

David Bashevkin:
It’s not a lineup of people?

Mark Moskowitz:
Oh no, no, no. I just surrendered myself that day.

David Bashevkin:
Okay.

Mark Moskowitz:
What happens is-

David Bashevkin:
Yeah, coming up, to me, anything I know about prison is from “Shawshank Redemption.” So-

Mark Moskowitz:
It’s a good movie and there’s a legitimate part. So if you’re remanded in a county facility … So remember where Epstein killed himself, was Manhattan correctional?

David Bashevkin:
Yeah.

Mark Moskowitz:
So if you’re in MCC and you’re waiting to go, once a week there’s buses that go out to all the different prisons. So if you’re sentenced to Danbury in Connecticut, there’s going to be a bus that takes you to Danbury. And you could have 30 guys on that bus that all have to … But because I was a self surrender, I was able to just go-

David Bashevkin:
You didn’t show up in shackles on a bus.

Mark Moskowitz:
I didn’t up in shackles on a bus.

David Bashevkin:
Gotcha.

Mark Moskowitz:
So when I say my experience was different, and I guess as good as it could have been for what it was, these are part of the things I’m alluding to, but you’re still just a total shell of a human being, you’re miserable. You don’t care.

David Bashevkin:
What’s the uniform?

Mark Moskowitz:
The uniform is just olive green, buttoned down and pants. Nothing fits you. Everything’s gigantic. They give you boxers that have probably had 50 asses in it as they made these things. God knows who was in these things. Shoes with no laces, so you can’t hang yourself, so that’s a big thing.

David Bashevkin:
Oh, you have prison shoes?

Mark Moskowitz:
No belt. Yeah, there’s prison shoes until you get to the camp where you’re getting acclimated. Then you meet with the camp advisor and he does an intake evaluation. And he takes your picture and gives you an ID and sort of tells you how life is going to be. They give you a bed roll.

David Bashevkin:
It’s like an orientation.

Mark Moskowitz:
It’s an orientation, and this part freaked me out. He’s like, “Okay, go walk over to the camp now.” I’m like, “By myself? What do you mean go walk over to the camp?” He goes, “Yeah, go walk over to the camp.” And then he says something like, he’s like, “Moskowitz, I know you’re not going to run away. Don’t worry about it. I’ve seen a million a guy like you before. Plus if you run away, you’re going to get five more years on your sentence,” I think something like that. So they know what, they’ve seen these guys. They’ve seen a million people like me.

So I walk over there, holding up my pants because they’re too big, got my bed roll. And I remember thinking, how am I going to brush my teeth tonight? Something so simple, but powerful. I brush my teeth before I go to bed. How? I don’t have a toothbrush. I don’t have toothpaste. I don’t have the most basic needs of society. How am I going to get all this stuff? So I get to the camp, the CO at the camp meets me, and then he introduced me to a couple guys who give me a deeper orientation about, then these are inmates, how to use the phone system. How to-

David Bashevkin:
The inmates teach one another.

Mark Moskowitz:
The inmates teach one another. The truth is, and this is in all levels, the COs don’t want to have any interaction with the inmates. They don’t care, just don’t make their life more difficult. They’re government employees. They don’t want their life to be difficult. They just want to collect their paycheck and go home and it’s safe every night. So these two guys give me the introduction, and then they introduce me to someone who is in charge of the Jewish inmates.

David Bashevkin:
Is that an inmate or it’s a-

Mark Moskowitz:
It’s an inmate. And what’s interesting is probably the most segregated place in this country is prison, but it’s for a reason. And that is, people hang out with the people they want to hang out with. So you have someone who’s, what they call the shot caller. The shot caller for the blacks, the shot collar for the Latins, the shot caller for the Jews, and this is all accepted behavior.

David Bashevkin:
Inside the prison system?

Mark Moskowitz:
Inside the prison.

David Bashevkin:
Shot caller, meaning what?

Mark Moskowitz:
Shot caller meaning, they’re in charge of that group.

David Bashevkin:
They’re like the Morgan Freeman, the Red?

Mark Moskowitz:
I guess that’s probably a good analogy, sure.

David Bashevkin:
“I’m going to find things from time to time.”

Mark Moskowitz:
Yeah. And he gave me a toiletry kit with stuff in it.

David Bashevkin:
He did?

Mark Moskowitz:
The guy. Yeah.

David Bashevkin:
Is it prison-approved or he just-

Mark Moskowitz:
No, it’s prison-approved. It’s all-

David Bashevkin:
But he’s the one who just runs the show?

Mark Moskowitz:
He’s the guy who runs the Jewish show, yes.

David Bashevkin:
How long is this person in prison for?

Mark Moskowitz:
Well, he was in prison a long time. He was in prison like 15 years. He got out a little bit before me. I don’t want to mention the name because it’s not my place. But he was also the gabbai when I was there.

David Bashevkin:
Well, I want to get to the religious life in prison in Otisville in a second. This is fast.

Mark Moskowitz:
It’s a lot to unpack, I know.

David Bashevkin:
No, there’s a lot here. You get to your cell, you have the same cell throughout your stay?

Mark Moskowitz:
So another advantage of being in a camp is that you’re not in cells. You’re in a dorm style.

David Bashevkin:
Oh, interesting.

Mark Moskowitz:
So when you first get into the camp, at least this was how Otisville, I was never in another place, but you get put into a small dorm where for the couple of weeks you’re just trying to learn the ropes. You don’t get a job yet, you just kind of learn the ropes. Then you get moved into the general population of the place. I mean, you’re still free to roam around and walk around and everything. But there’s a lot of etiquette in prison. People do have their own seats. People do have the televisions, there’s a television for each group.

David Bashevkin:
Gotcha. What channel? You don’t just show up-

Mark Moskowitz:
You don’t just show up and change the channel unless you want to get the crap beat out of you. Exactly. And then there was a TV for a friend of mine who got it at 10 o’clock at night. So he would start watching TV at 10. So there’s no cells, we lived in dorms. I started out in this one area and that was actually near the library, so that was not a bad place to be. Then you get moved into the general area, where it has-

David Bashevkin:
Is it a big room with bunk beds?

Mark Moskowitz:
It’s a big room with bunk beds, so there’s 50 on each side. So there’s about 120 people in total I think-

David Bashevkin:
And somebody gives you a … says, “This is your bed”?

Mark Moskowitz:
They give it to you. This is your bed.

David Bashevkin:
Do you want a top bunk or a bottom bunk?

Mark Moskowitz:
I didn’t have a choice. I was healthy, so I got a top bunk.

David Bashevkin:
Uh-huh.

Mark Moskowitz:
The average age at Otisville is pretty high compared to most prisons. I would say, when I was there, it was probably 58 or 60.

David Bashevkin:
Wow.

Mark Moskowitz:
You have a lot of people who were in their 70s who really couldn’t get around. They probably should have been in medical facilities. So, they would all get assigned to the bottom bunk. So, I was always on a top bunk.

David Bashevkin:
Gotcha.

Mark Moskowitz:
Which was fine. I mean, it took me two months to just get used to my back not hurting. I mean, you’re sleeping on a metal slab with a two inch thick mattress. It’s super uncomfortable.

David Bashevkin:
And is wake up, is that enforced, or can you sleep the day away? What are people doing?

Mark Moskowitz:
Some people did, but you have to work, it’s a working camp. So basically the camp …

David Bashevkin:
Do you get paid for that work?

Mark Moskowitz:
You get paid. I think I was getting paid $20 a month.

David Bashevkin:
Okay.

Mark Moskowitz:
I worked in the warehouse, which was great. That was definitely a Red thing, because you worked in the warehouse, so, when bananas came … When the food came in, you got an extra banana for yourself, or you could make yourself eggs in the morning …

David Bashevkin:
Gotcha.

Mark Moskowitz:
… as opposed to eating whatever they were going to serve you. So there were some benefits to working in the warehouse. I learned how to drive a forklift, so now I have skills and all that stuff.

David Bashevkin:
Oh, you did?

Mark Moskowitz:
Sure.

David Bashevkin:
That’s cool. So tell me about, and this is a sensitive subject, I mean, I know at least two or three people who have spent time in Otisville and it has developed a reputation as a very friendly prison, so to speak, to people specifically from within the Orthodox community. And I’ve always had mixed feelings towards that, because on the one hand, it is deeply moving, particularly the work of Aleph in serving all of the population, particularly people who are incarcerated, who should not be forgotten and giving them their religious needs.

In another, you don’t feel a sense of pride when a religious denomination or movement have a specific prison that is associated with a religious movement. I’m curious for you, because you weren’t raised within the Orthodox community. When you first came there, you were a Reform New York Jew. You came to Otisville. Were you taken aback by the Orthodox presence there? How did you react to that?

Mark Moskowitz:
I had been told that there’s a lot of Orthodox people there.

David Bashevkin:
Somebody said that in advance?

Mark Moskowitz:
I knew that.

David Bashevkin:
It has that …?

Mark Moskowitz:
Yes. I knew the reputation that you’re alluding to, but, I think growing up secular, you tend to feel that there is a big divide between observant and non-observant Jews. And that maybe observant Jews look down on people who grew up…
But I think for the most part, the attitude there was that a Jew is a Jew, and if you’re there, you should try to live your life as best you can and learn. For me, it was a big part of the whole story, was being in a place that had a lot of people who were observant Jews. It taught me a lot about the religion.

David Bashevkin:
So tell me, what is religious like for you now in Otisville? Is there minyanim, is there daveningthree times a day? Shacharis, mincha, maariv?

Mark Moskowitz:
Yes. So the prisons have to provide kosher food.

David Bashevkin:
Okay. What’s the food like?

Mark Moskowitz:
Terrible.

David Bashevkin:
Terrible.

Mark Moskowitz:
Correct.

David Bashevkin:
Worse than airline food? I’ll be real here.

Mark Moskowitz:
I think so.

David Bashevkin:
I love airline food.

Mark Moskowitz:
Oh, okay.

David Bashevkin:
I request doubles, if there’s extra.

Mark Moskowitz:
There was very little to love. It was all these frozen meals that we would get.

David Bashevkin:
Okay.

Mark Moskowitz:
And they were kosher and we had our own little kosher kitchen.

David Bashevkin:
And did you keep kosher before you were in prison?

Mark Moskowitz:
No, no.

David Bashevkin:
Why keep kosher in prison? Because?

Mark Moskowitz:
Well, I didn’t really start out keeping kosher, right? So, the guy who was the gabbai, who gave me the toiletry kit and everything.

David Bashevkin:
The shot caller.

Mark Moskowitz:
The shot collar, exactly. The shot caller. He’s like, “Hey, why don’t you come put tefillin on?” So I’m like, “Okay.”

David Bashevkin:
Had you put on tefillin before?

Mark Moskowitz:
For my bar mitzvah and a couple of times other than that. But if I said five in my life, that’s probably around the right …

David Bashevkin:
Okay.

Mark Moskowitz:
So I went in, showed me how to do it. I’d say shema, from what …

David Bashevkin:
Remembered.

Mark Moskowitz:
… I remembered of it. Exactly. And then that was it. I’d be in and out in a few minutes, right? And I was still eating on the non-kosher line. So I was eating regular food, which consisted of pork and all the other.

David Bashevkin:
Was it better?

Mark Moskowitz:
Some meals were better. I mean they definitely, so inmates run every part of the camp in terms of the kitchen. So you had some inmates who were really good cooks and they would try to spice the meals up a little bit and make it good.

David Bashevkin:
Depends who was cooking that day.

Mark Moskowitz:
Depends who was cooking, exactly. But in the kosher kitchen, they basically just heated up the frozen meals. So as I started to put on tefillin more, and I guess this coincides with as I started to do my own work on me, which is a super important part of the story, as I started to want to heal myself. And I guess to just go back a little bit, when I surrendered, I was really hopeful that the government had a plan. Like, okay, they’ve done this with a lot of people. I’m sure they figure out how to do it. The truth is they don’t care. Prison is not there to rehabilitate you. It’s there to punish you. And that is a fact that you learn very quickly. But I still had this really deep desire to fix it. When you wake up in prison, if you don’t think that you need to fix yourself, then you’re really delusional.

David Bashevkin:
Something led to you being here.

Mark Moskowitz:
Exactly. Whether you think you’re guilty of your crime or not. You have all this time, you have no cell phone..

David Bashevkin:
Something went wrong.

Mark Moskowitz:
Something went drastically wrong. You have no cell phone, you have less distractions than in the outside world. There’s got to be a reason. And as I started to try to work on myself, I didn’t know how to do it. I’ve been trying to work …

David Bashevkin:
So what does that mean?

Mark Moskowitz:
I’ve been trying to work on myself for 40 years. I mean, I was the person who was going to Tony Robbins seminars.

David Bashevkin:
You were.

Mark Moskowitz:
I was reading the books that were written by Jim Rohn and these people who were just …

David Bashevkin:
Self-help.

Mark Moskowitz:
… pinnacles of the self-help industry. And I never figured it out. So I was pretty distraught there after I really realized that there’s no plan for me.

So one of the blessings of having gone through all that work, even though it was “failed work”, was the common theme in all of those writings is about gratitude and how you have to live with an attitude of gratitude. So I didn’t know what to do. I didn’t really know what that meant. So one day I was just going for a walk around the camp and I took off my headphones because I was listening to the radio that they give you.

David Bashevkin:
They give you a radio?

Mark Moskowitz:
They give you radio. Because all the TVs have to have a radio frequency. There’s no volume.

David Bashevkin:
Oh, gotcha.

Mark Moskowitz:
That way we don’t have arguments with people about how loud something is.

David Bashevkin:
Gotcha.

Mark Moskowitz:
So I took out the thing and I just was like, “I’m thankful that I’m here and I see pine trees.” I don’t know, something stupid, right? And I just started saying things I was thankful for. I’m thankful that I can actually walk. I’m thankful that I have three meals. I’m thankful that I have a place to sleep. And it started to feel a little bit better. It wasn’t great. It was just the first time doing it, but I got it. I’m like, “You know what? I don’t know what else to do. So this is what I’m going to do. This is going to be my thing.” And every day I would walk around the camp and I would talk about being grateful. I would say, “I’m thankful for this. I’m thankful for that.”

David Bashevkin:
Talk to who?

Mark Moskowitz:
Myself, just myself. And I would say it out loud and I would, if there was a cloud that looked like something, I’m saying I’m grateful for that cloud, whatever it was. And it started to become, I could start to feel a change in me. And I was starting to go to shul and I was putting on tefillin and I was doing this and it took about three months of this every single day. I didn’t skip a day.

David Bashevkin:
You checked in when?

Mark Moskowitz:
September.

David Bashevkin:
You checked in before the high holidays or after that year?

Mark Moskowitz:
I think before.

David Bashevkin:
But you definitely spent Rosh Hashanah and Yom Kippur in prison.

Mark Moskowitz:
Oh yeah. No, I spent two.

David Bashevkin:
But that first one was just right after you left.

Mark Moskowitz:
The first one you were there, exactly. You’re just, your head’s ready to explode.

David Bashevkin:
You basically shifted. You spent your whole life trying to figure out how to make other people appreciate you or doing the right movements, never figuring out how to fill up your own tank. And you’re sitting and walking by yourself in prison and you’re saying, “Let me figure out what I can still have gratitude for, even in this darkness, even in this prison.” And it starts to shift the locus of your perspective almost, where it’s not about, what does this person want to hear, but you’re finally talking literally to yourself.

Mark Moskowitz:
That’s profound. What the shift was for me was, I stopped trying to be grateful and I became grateful. It was being what I wanted to be.

David Bashevkin:
Embodying it.

Mark Moskowitz:
I was embodying it. Yes. So it was this time where all of these walks compounded over time, changed and I learned this later as I got out of prison, it literally was neuroplasticity in my brain. It changed the way my brain was thinking.

David Bashevkin:
The way you processed information in the world.

Mark Moskowitz:
The synapses in my brain literally changed from anger and hatred and blame and all those other things to feeling gratitude. And at first there were things I could not be grateful for, even though I wanted to be. I would say, “I’m grateful that I have three children in my life.” But my brain rejected that because I was estranged from them. I didn’t know where their life was. But as the veil of all that negative emotion started to lift, I was able to say these things and really truly mean them. And really just be happy for my health and be happy that I’m in a place where I don’t have to worry about my physical safety and being in a place where I can explore religion that I never really explored. That became part of my gratitude.

David Bashevkin:
Did you start studying? I mean, you were showing up to prayer.

Mark Moskowitz:
I was showing up to prayer a lot of … I would mostly go to maariv.

David Bashevkin:
Maariv‘s my favorite, too. If I had to pick one prayer to attend to, for sure in prison, it would absolutely be maariv.

Mark Moskowitz:
That was the big one, too.

David Bashevkin:
It’s like the close of the day.

Mark Moskowitz:
The secular people all seemed to want to go to that one, right?

David Bashevkin:
Maariv.

Mark Moskowitz:
So, we all knew what Aleph was doing on the outside and what a few of the inmates were doing on the inside to try to help the Jewish community.

David Bashevkin:
Sure.

Mark Moskowitz:
We had challah on Shabbos we had grape juice on Shabbos

David Bashevkin:
On Shabbos are people singing zemirot?

Mark Moskowitz:
For sure. No, it’s a big deal. We had a family there. Again, I’m not going to mention names, but we had a family there, they were all cantors and they had these great voices and they would sing all night. So we’d have our Shabbos service on Friday night, we’d have a nice dinner afterwards and they’d spend three hours singing. And it was actually pretty cool. And for me, not …

David Bashevkin:
Did the non-Jews know what was happening?

Mark Moskowitz:
Everyone there knew that the Jews made the place what it was and they benefited from it because they would get better food because of it. And they would get, if we had chicken and they could get some of the chicken, if we hired a couple of Shabbos goys to help us out with air conditioning and with serving the food, to cook the food and they would benefit from that.

David Bashevkin:
I’m torn. There’s something very beautiful about people connecting to their Judaism and their Yiddishkeit no matter the place, no matter where they are. And there’s something that I’m processing, I’m uncomfortable with. I think particularly growing up in the part of the Orthodox community that I have of valorizing prison. This struggle that our community and the way that we look at white collar crime is a little flap. “Okay, nu, nu it doesn’t hurt your reputation in the same way.” I am deeply uncomfortable with it. You didn’t come from that world, but even the language that we use, I’ve heard people say, “Oh, they sat”, that’s what they call it. They sat. And there are so many things and expectations in the Orthodox world that can have you ostracized. The list goes on. Well, social religious expectations.

On that list unfortunately is not prison. But I’m not saying that we should ostracize anyone, but once we’re ostracizing, it’s always strange to me that we have no problem with somebody who has financial issues and they could come right back into the community and get all of the honorifics and this and that. But there are so many other religious issues that we do ostracize for and it just feels dissonant to me.

Mark Moskowitz:
To speak to that point a little bit, I will tell you that I felt that there was little remorse from that group. Very little remorse. I think they treated it a little bit like yeshiva. They learned a lot, which is, that’s their right to do that. They had a lot of visitors, like you said, they didn’t seem to be at all ostracized.

David Bashevkin:
It’s like the price of doing business a little bit.

Mark Moskowitz:
There seemed to be very little remorse and maybe because you did have the ability to keep up with your studies and learn and you had a group of, let’s say there was 120 inmates, about half were Jewish and about a third of those, maybe 18, 20, 22, were real frum-type people.

David Bashevkin:
For you it’s such a different experience. You’re being taken out of your world. That’s not your comfortable world that you grew up in. So you don’t have that same support. And I’m not condemning, I love that they provide this support. I think it’s very powerful. I just wanted that noted that your ability to really reflect and go on those walks alone was prompted by having that sense of loneliness, which is only there if you’d look at it as otherworldly that you’re here.

Mark Moskowitz:
And that’s what I did. That’s how I embrace it. I did think to myself that all the steps that led up to me being in Otisville. I mean I probably had very little faith in God prior to that.

David Bashevkin:
I mean, did you think about God a lot? Was that …?

Mark Moskowitz:
Only in a blasphemous probably way, right? Only in a way of, “How could you possibly be putting me in this situation again? Why is it me, God, what did I do?” But I learned that A. There is definitely a God and God definitely loves me and loves everybody. I would never think of God as being vindictive. I think free will is the greatest thing he could ever have given us. And the idea of being made in God’s image when I was more secular, to me that was more of a physical image. That’s how I always thought of it, right? The flowing white robes and all the beard and everything like that. But now I know that being made in his image means that we can create the life that we want to create for ourselves.

David Bashevkin:
So, fascinating taking me through that world inside of prison. I want to fast forward to the exit and the life after. When your sentence is coming complete. I mean, did you keep track of that day? Are you writing the little lines on the wall?

Mark Moskowitz:
No, because you don’t really know exactly when that day is. Because what happens in the federal system is you get sentenced and then you serve 85% of that sentence. The other 15% is known as good time. So it’s time that they give you automatically. So in my case, that was like five months. So I was doing 28 months. And you can lose that if you don’t behave.

David Bashevkin:
Let’s fast forward. You have your date when you’re going to leave.

Mark Moskowitz:
I got the date of September 11th, 2019 and I was going to halfway house and then going to home confinement for the rest of it. And I had no home. But a friend of mine offered to let me live with her just out of the kindness of her heart. Just a very dear friend of mine. So I get notified a month early, call up everyone I’m getting let out, get to go to the halfway house, which ultimately was terrible. I would never recommend going to the halfway house because it was awful.

David Bashevkin:
Worse than Otisville?

Mark Moskowitz:
Way worse. I mean, you’re in with everybody. In Otisville, you’re all within the non-violent criminals. In the halfway house in Newark, New Jersey, you got people from all levels of prison and they were all pretty bad people. They weren’t going to hurt you and you’re living together and they wouldn’t hurt you because they don’t want to go back to prison. But there they didn’t care if you smoked cigarettes or smoked K2, which was synthetic marijuana. So there were guys high there all the time. It was not a good place. And there you’re on lockdown 23 hours a day.

David Bashevkin:
Gotcha.

Mark Moskowitz:
So, thank goodness I got a job after two weeks and then I was only there another two more weeks.

David Bashevkin:
What was your job?

Mark Moskowitz:
I was working for a guy in Brooklyn in a kitchen construction company. And I had gotten that job from someone I was in Otisville with. So it was all, worked out.

David Bashevkin:
When you leave Otisville, you giving hugs? Handshakes?

Mark Moskowitz:
Everyone gives you a little party, throw away. You can’t stay in touch with anybody until your off supervised release, which for me will be January. But there’s an important part to the leaving, which I want to touch on. And that is I figured out what had ailed me in prison. I understood about self-esteem and self-worth and how I had unhealthy self-esteem. I read a couple of really deep books on that, which helped me.

David Bashevkin:
We’re all about books. So if any book recommendations, I would love to hear some of those.

Mark Moskowitz:
So the first book I read was called “The Six Pillars of Self-Esteem” by Nathaniel Branden. And that was a very good book. It was a thick book. It was technical. As I was starting to become more observant and going to shul more, my father had passed away while I was in prison and I was saying Kaddish for him.

David Bashevkin:
Did they let you go to the funeral?

Mark Moskowitz:
They let me go to the funeral. So, he passed away in June of 2018. So, when I came back the gabbai said to me, “You could say Kaddish for your dad.” I’m like, “That’s not really what I do. That’s not who I am. We’d say it for a few days shiva, but that’s it.” He’s like, “Look, you’re here, why don’t you do it?” So, I thought about it and I started saying Kaddish for my dad.

David Bashevkin:
Every day?

Mark Moskowitz:
Three minyanim a day.

David Bashevkin:
Wow.

Mark Moskowitz:
I think I missed five or six over the course of that entire 11-month stretch. And that was very transformative for me.

David Bashevkin:
Going every day, several times, three times a day.

Mark Moskowitz:
Going every day. That’s where I really fell in love with Judaism, I guess is the best way to put it. Because growing up secular, you think that organized religion is a hindrance to spirituality and saying the same prayers, three times a day, every day, once you start to know them, I mean, I could speak a little Hebrew, I could read a little Hebrew, but to really get to know them took me three or four months. I was really able to meditate as I was saying them and really think about the words and really think about what they mean.

David Bashevkin:
The familiarity almost. It’s a window. I actually agree with you. I think even spacing out during prayer is a part of the prayer experience. And you come back to the words and you come back to the experience. It’s very meditative.
So come back, I want to allow you to finish this idea of this healing. You’re reading these books on self-esteem and the breakthrough is what?

Mark Moskowitz:
So, I read this first book from Nathaniel Branden, and then I was given a book by another person, very observant person. It was a book by a guy named David Lieberman.

David Bashevkin:
Sure. Psychologist in Lakewood.

Mark Moskowitz:
Psychologist in Lakewood. Exactly. The book’s called “Real Power.” It was a much thinner book than the first book I read. But I remember getting to the early part of the second chapter. He started talking about ego and self-esteem and how they’re not correlated to each other, right? They’re completely uncorrelated. And when your ego is high your self-esteem is low. The way it hit me was really like, wow, that was it. That was what had plagued me my whole life. And it’s a really important part of the story because I feel like the story unfolded correctly for me. I started out with gratitude. My father passed away and I believe that his passing while I was in prison was a gift that he gave me. Because we had had a strained relationship, I felt that he gave me in death what he could not give me in life. He knew that I was going to need this and he was willing to move on.

Here I was in this super religious or observant place, the gabbai says, “You should do this.” How do you not do that? How could you be blind to all of those signs and signals? Then this gentleman gives me this book, “Real Power.” And that just sets off a firestorm in my head. And when you’ve been struggling with something for so long and you don’t know what the answer is and you can’t figure it out intellectually, but then you do get it. It is the most uplifting feeling in the world. All of the stress, all of the anger, all of the negative emotions were just gone, in a second.

David Bashevkin:
It’s liberating. I mean, it’s so fascinating to have a liberating personal experience behind bars, in prison, which is really, really powerful. I’m curious now. You go through this halfway house. You’re no longer in prison. You mentioned you’re still at the tail end of supervised release. So you’re checking in with …

Mark Moskowitz:
Once a month I just have to fill out an online form.

David Bashevkin:
Oh, online. You don’t even have to go down to …

Mark Moskowitz:
No, I’m on what’s known as the low intensity caseload list. So they don’t …

David Bashevkin:
They don’t have time.

Mark Moskowitz:
They don’t have time.

David Bashevkin:
Did you ever reach out again to investors who felt betrayed by you and what did you do to try to piece back together the relationship with your children? What were the acts of reconciliation that take place after prison, so to speak? In prison seems very internal. Now you’re out, you’ve rejoined the world. Where does that reconciliation begin?

Mark Moskowitz:
Well, I was advised by probation to not reach out. Their main focus is making sure you don’t go back in.

David Bashevkin:
Gotcha.

Mark Moskowitz:
Recidivism rate is quite high in terms of people going back. So they don’t want that to happen. They want to keep you out for the most part. So they tell you not to reach out until everything’s over because something can get misconstrued. Someone could be angry. They really wanted to be very careful about that. So I have had conversation with one or two, but they reached out to me.

David Bashevkin:
They did.

Mark Moskowitz:
And for the most part they were like, “Look, I hope you did okay. I hope you figured it out.” Somewhat supportive.

David Bashevkin:
That’s actually quite beautiful that they did that.

Mark Moskowitz:
With my children it’s been an interesting road because I know some of the guys at Otisville would write their kids every week. I always felt that was just a lot. It’s heart-wrenching enough to have your dad in prison. You don’t need that reminder every single week.

David Bashevkin:
I totally hear that.

Mark Moskowitz:
So my feeling has been one of the things which, after I learned about self-esteem, I really started understanding about taking responsibility for my life, which is a big part of the story. If your self-esteem is low, you have a hard time taking responsibility because you can’t see yourself as the problem. You see everyone else as the problem. The last lesson I learned was about acceptance and accepting people and circumstances for what they are. Essentially understanding that you could control your own actions, you can’t control other people.

So I have taken on a posture with my children that I reach out to them when I feel necessary. There’s no schedule. They all know I love them. They all know that I want them back in my life. They all know that I’m interested in them. They also know that I’m letting them do the work that they need to do when they’re ready because I find that to be very important. They live with their mother and their mother and I do not have a relationship. So I’m sure that’s a big part of the stress on them anyway. And I don’t want to add more stress to their life. So, I’d say every six weeks, every four weeks or something, or if a birthday comes up …

David Bashevkin:
And they know where you are.

Mark Moskowitz:
… just want to let you know I’m thinking of you, hope you’re doing great.

David Bashevkin:
They know that love is still there.

Mark Moskowitz:
They know that love is still there. And I think that’s all I can really do at this point. And I have to let them be on their own journey and you know something? I think we need to trust in other people that they’re going to eventually do the right thing and they’ll eventually come around.

David Bashevkin:
It’s the inverse, it’s something so moving to me where you spent the first half of your life as a people pleaser, being surrounded by relationships that were conditional on your success, on your status, on your wealth, on your income or whatever it is. And part of what allowed you to change in this second chapter of your story is the inverse of people pleasing, of conditional acceptance, which is unconditional love and being able to provide that regardless of whether or not it’s reciprocated to the same degree that you put it out there in the world is something incredibly moving, incredibly beautiful. And there’s a reconciliation of sorts. It’s a part of allowing relationships to endure and persist. Not on a reciprocal basis, not because you do for me, so I’m going to do for you. But this relationship in and of itself has value and dignity and I’m going to be there no matter what to continue it.

So really this story is incredibly powerful and your experience and all the work that Aleph has done in serving this. I always conclude my interviews with more rapid-fire questions. The first one that you’ve already addressed, I always ask for great book recommendations, particularly about the topic that we’re talking about, the general topic of teshuva, of self-transformation. You mentioned the book on self-esteem by Nathaniel …

Mark Moskowitz:
Branden, “The Six Pillars of Self-Esteem.”

David Bashevkin:
And also …

Mark Moskowitz:
“Real Power” by Dr. David Lieberman.

David Bashevkin:
Anything you want to add to that? Two books is already more than one, so I don’t want to put you on the spot.

Mark Moskowitz:
Do you mean in the same genre, of self-help or?

David Bashevkin:
In this universe or something that helped you on this journey, but if those are the two?

Mark Moskowitz:
I love the works of Dr. Joe Dispenza.

David Bashevkin:
I’ve never heard of him.

Mark Moskowitz:
He believes a lot in the quantum mechanical field and how our brain can really help us focus on what we want out of life. And what I talked about when I said God created us in his image, that we have the ability to create our own lives.

David Bashevkin:
Construct our own reality.

Mark Moskowitz:
You know something? This is my own thing, it’s not a book. But when you have perspective on life and when you go to prison, you come out, you have perspective… Even being stuck in traffic doesn’t seem so bad. Life is not so bad. So, you develop this perspective. And there’s another gentleman named Wayne Dyer who is a modern day philosopher and he says something. He says, “When you change the way you look at things, the things you look at change.” And it’s so true. If you look at a person, I think you did a great recap in terms of my life of accepting other people for who they are. I could still be this bitter and angry person if I wanted to be, and I could be mad at my children for not having me in their life just now. But I don’t look at it that way. My whole perspective has changed, my whole thing has changed. So those are great authors. Any book you get from them is going to be great.

David Bashevkin:
Something tells me I already know the answer to my next question. I’m always curious, if somebody gave you a great deal of money that allowed you to go back to school and get a PhD in whatever subject you wanted, what do you think the subject and title of your dissertation would be?

Mark Moskowitz:
Well, it would definitely be about self-esteem. Understanding that we all have the power within ourselves to have the best life we could ever imagine. We do not have to look outside of ourselves for validation, for excitement, for joy. It’s all within us. It’s all how we look and model the world. So, I don’t know if I would actually go for a psychology degree. I might go more for a philosophy degree.

David Bashevkin:
Sure, the thought experiment …

Mark Moskowitz:
I think it’s more philosophical than it is psychological because I spend so much of my life thinking about life and I love it. I meditate twice a day. I still pray, not as much as I did, but I still put tefillinon and I still do some levels of observance that I think are very important to me. My faith in God and my faith in myself are as high as they’ve ever been. I’m writing this book and it’s called “Within” because I believe that that is where all of our power comes from.

David Bashevkin:
My last question, I’m always curious about people’s sleep habits. What time do you go to sleep at night and what time do you wake up in the morning?

Mark Moskowitz:
Typically sleeping by 10:00, up about 4:30. So I get about six and a half, seven hours of sleep.

David Bashevkin:
Look at you. Early riser.

Mark Moskowitz:
I’ve always been that way. It’s the habit that I’ve always had and I love it, because you get a lot done. By eight o’clock in the morning, you’ve already had a full day.

David Bashevkin:
Mark, I cannot thank you enough for taking the time, telling us, sharing your story, your experience, your wisdom. It means so much.

Mark Moskowitz:
Thank you very much, David. It’s been my pleasure.

David Bashevkin:
I found Mark’s story incredibly moving, but I really wanted to also hear more about the Aleph Institute. There’s something very moving about a Jewish organization that dedicates themselves to helping people who are incarcerated. It’s not really a glamorous project, it’s not the type of mission that you want to announce and broadcast to the world, that you need their help. But in many ways it’s at the heart of the teshuva process. There is an incredible passage of Talmud that I always think about this time of year, particularly leading up to Yom Kippur.

The Mishna in Yoma says that part of the preparations of the kohen gadol was spending seven days before Yom Kippur isolated and separated from his house, from his family, in a part of the Beis Hamikdash that was known as the lishkas farhedrin, the chamber of farhedrin. And there’s something very strange that the Talmud says, that they did specifically in this place that the kohen gadol was isolated.

The Gemara says that this was the one place in the entire Beis Hamikdash, that they affixed a mezuzah. The Beis Hamikdash in general did not need mezuzahs, but the Gemara says the one place in the Beis Hamikdash that needed a mezuzah was lishkas farhedrin. Why did they have a mezuzah? So the Gemara says, “shelo yomro kohen gadol chavush b’beis ha’assurim.” So that people should not say that the kohen gadol was locked up in prison. And it’s such a bizarre concern. Really? Again, he’s preparing for the high holidays. We know why he’s there. Do people really think that? Were we really concerned that there’s going to be some blog post? There’s going to be chatter? Chatter at the weekly Shabbos kiddush. By the way, you know where the kohen gadol is? He’s locked up. He’s not really preparing it. They’ve got him in prison, they’ve got him jailed. That there’s going to be like posters everywhere, “Free the kohen gadol?”

What exactly was this concern that the reason why the one place in the entire Beis Hamikdashwhere they affix a mezuzah is on the chamber of farhedrin where the kohen gadol prepares so people don’t think that the kohen gadol is in prison. I mean, what kind of concern is that? Anybody who even knows this must know enough that we’re not locking up the kohen gadol. He’s got a big day coming up, he is preparing for something. Why on earth would anybody think that the kohen gadol is in prison? And I heard an incredible idea from my friend and teacher, Rabbi Yakov Glasser. I think so many of my teshuva ideas, anybody who’s had the privilege of hearing Rabbi Yakov Glasser Shabbos Shuva derasha at the Young Israel of Passaic Clifton knows exactly what I’m talking about.

But there’s something about the Torah of teshuvah in my mind, that in my life, that returns to the Torah of Yakov Glasser. Rabbi Glasser shared with me an amazing idea. So the reason why that we affix a mezuzah on this door, on this chamber that the kohen gadol is locked in is because we don’t want people to misunderstand what teshuvah is all about. That in the preparation, in the seriousness, in the intensity of teshuvah, one could think that the process of teshuvah is meant to be isolating. It is meant to be onerous. It is meant to be this difficult, painful thing that happens in the shadows, that feels imprisoning, that feels isolating. When, in fact, the process of teshuvahcannot feel like a prison. The process of teshuvah needs to feel redemptive. It needs to include, wherever you are and wherever you may be, your entire life. It needs to include your family. It needs to include your friends.

In the words of Rabbi Glasser, the reason why they affix the mezuzah is that they were deeply concerned that people shouldn’t characterize a religious experience of meaning and purpose as a confining suppression of opportunity and freedom. We shouldn’t look at this time of year as confining, as suffocating, as isolating, but each of us in our own lives need to find that mezuzahthat we hang up on the door of our teshuvah process to help us include the totality of our lives.

And I think there’s nobody who models those ideas and that experience than Rabbi Sholom Lipskar, the founder of The Aleph Institute. And I had the opportunity to speak with Rabbi Lipskar and ask him why was this organization started? Why is this something that the Jewish community needs to support, and why was this such a priority for the Lubavitcher Rebbe? It is my privilege and pleasure to introduce our conversation with Rabbi Sholom Lipskar.

Sholom Lipskar:
It was, the Rebbe, a number of times, public occasions, lamented the fact that there are so many of our brothers and sisters who are in limited environments, such as incarceration spaces. They are waiting for someone to come and to put on tefillin with them, to give them a good word, to encourage them, to show some closeness. And even though we’re all involved in outreach, et cetera, but that segment of society seemed to have been cast aside or not given attention. And the Rebbe, like Moshe Rabbenu, who took care of the smallest sheep in order to qualify for his role, the Rebbe cared about every single Jew, no matter where they were and what conditions they were. And so after that public talk, I had opportunity to interact with the Rebbe on my work and the Rebbe kind of recommended that God will give me a good thought. That when I asked the Rebbe about this idea that he was talking about, the Rebbe was very positive or that encouraging in so many ways.

So I realized that that was of something of great importance to him, especially as the Rebbe said, that when you take a look at any society and you take a look at how that society is conducting itself and you want to uplift that society, like you want to lift up a building. When you lift a building, you can’t put or grab the building at the top, pull it up, because then half the building will tear away from its origin. The way to lift a building is putting the lever under the bottom of the building and when the building lifts a moment or an inch, the top lifts an inch as well.

And so we have to address even those that are perceived as the lowliest of our society. And in actuality, they must have the greatest potential. The Rebbe explained one time when he gave a talk to 20 prisoners, at a fabrengen that we arranged, gathered the Rebbe. The Rebbe talking to them about their unique role and how we are in a triple prison, because the soul comes down to earth, already it’s in a prison. The soul does not want to enter into this physical, materialistic, very provocative world that causes so many challenges, et cetera as we know.

And so the soul doesn’t want to come down. So that’s the first mission that God puts us into. And that when the soul is finally in the body, we are in an exile, a double exile out of our holy land. And even if we are in our holy land, it’s not a time of exile, we’re still concerned and worried that we have not yet transformed battle tools into agricultural or productive tools as the prophet tells us that will happen. So we are in exile within exile, double exile. And then there are certain people that are in a prison which then is a triple exile. The purpose of exile, the Rebbe says, is not to put a person in a difficult position but is to elevate that lonely space. And not everybody has the capacity to do so. One must have fortitude and strength, courage and to go against every odd. And so, the Rebbe, in some way elevated their spirit by telling them how important a mission they have to bring even holiness into such an empty space like a prison that is not obligated to have a mezuzah. That’s how distant it is from any aspect of holiness.

So we started working in a particular prison, working with the men in prison and working with their wives and with them as a family, and we thought that spirituality was extremely powerful and meaningful in that environment that we found. We called it The Aleph Institute because the aleph, first is the beginning of the first letter. It’s a new beginning. It’s a new opportunity to, when you put aleph into the word Hebrew, which represents exile, which is gola, but aleph spells geula, which is freedom.

David Bashevkin:
Wow. Beautiful.

Sholom Lipskar:
So that’s another aspect of reality. By divine providence, we started a pilot project in one prison here in South Florida, a federal prison, where there were about 20 something Jews of different caliber there for different reasons. A lot of them were in there for financial crimes, drug programs, importation of marijuana at that time, 1980s, et cetera. I got a very, I might say, openminded chaplain and went along with my programming and I started a program to study with these people every week for three hours, then I studied with their wives in a home in the neighborhood three hours a week. So to create a kind of interaction that once every month the chaplain would allow us to bring the wives and husbands together for a joint study, which really created some very positive influences in the wives and children, et cetera. The men became extremely inspired by their Jewishness, decided they wanted to be kosher, they wanted to put on tefillin and asked. The warden in that particular environment was a multi-generational antisemite and his father was a warden, his grandfather and they were torturous people and he really was nasty. I asked him about kosher and he said, “Oh don’t tell me what the Bible says.” Kind of was really not a very blessed kind of interaction with that particular person. But we had access to Washington and they gave us, made sure that it was kosher to somebody at that particular prison. And what happened was, once the people, they were so upset about not eating kosher, that they went on a hunger strike one day. The next day, we called it Tuesday morning massacre, all 20 guys were rounded up early in the morning taking their stuff and they would put it, it’s called diesel therapy.
Diesel therapy is when you move someone from prison to prison. But instead of flying someone from Miami to New York, to put them in a New York prison, they’ll take them on a bus and go through all the way to the West Coast and back up the West Coast to the East Coast and they’ll take… that trip could take anywhere a week to six months and on the way they stop off at local prisons overnight and all day they’re in a steel bus with their hands and feet shackled. So all of a sudden were shipped, little did they know, they tried to kind of stop the programming because we were very active at that time and this group was very tight and they ended up in 18 different prisons. And all of a sudden I was getting those 18 different prisons, we need a pair of tefillin in here. We need some books here. We don’t have any Jewish programming. So little did they know that by kicking out the group, that pilot project actually started a national program which was very effective and we were able to show cause to the authorities the benefits of our programming, how it made a prisoner more of… a model prisoner.

David Bashevkin:
I found that analogy of lifting up a building incredibly moving and incredibly beautiful. Part of the difficulty is that you are serving a population that it’s very clear that they did something wrong, they committed a crime and we’re discussing this notion of teshuvah and they’re sitting there, they’re doing the time for their crime as they say in America. I’m curious what notion of teshuvah, improperly translated as repentance, but they’re already in prison. So what can the notion of teshuvah provide an inmate above and beyond the prison experience that it’s already giving them? What are you emphasizing that is different?

Sholom Lipskar:
That’s a good question. We have a very straightforward response to that. First of all, I want to just make a note, that when you say they all did something wrong. A very world class jurist who was a chief judge at the Eastern District for many years, Jeff Weinstein, an icon of… we started The Aleph in his chambers actually. And he said to me one day, he said, “Rabbi, we should change the name of Aleph to the There But For the Grace of God institute.” Because here in America you find some stain on everybody. So let’s just say, for every guy that’s inside, that’s been caught, there are a few guys outside that haven’t been caught.

And in terms of teshuvah, we get them to understand. First of all, there’s five levels of teshuvah, according to Maimonides. There’s five different degrees that you have to address. But number one, you have to realize that when the Jewish people came out of Egypt called yetziat mizraim, out of enslavement, but we weren’t out of enslavement. We went to, we had to go… we argued about water, we wanted to come back so many times we weren’t free until we came to Israel. Freedom is not a geographic or external state, it’s an internalized state where you could be in a penthouse here in Val Harbor, you could be in prison. And you could be in prison, and you could be free depending on what your state of mind. It’s a very important segment.

So even when you’re in prison, if you’re angry, you’re blaming people, bad judge, bad witnesses, bad lawyer or luck, whatever the case is. And then you also are going through anguish because you’re not able to address your wife and children in a proper matter, et cetera, and you’re afraid of what this future will hold for that. So there’s many factors. So teshuvah number one, there’s five levels. Level number one is, you got to know that you did something wrong. Knowledge. Which means if you argue I didn’t do anything wrong, forget about it, you’re not going anywhere.

In fact, in our alternative sense, we go in front of a judge to ask the judge to give an alternative sentence. It mitigates the harsh consequences and collateral damage in prison. One of the fundamentals, we will not represent anybody who said they’re not guilty.

David Bashevkin:
Wow.

Sholom Lipskar:
Not guilty, then we can’t help. You’ve got to go in there with your lawyer and argue, then that’s not our job. But if you feel that you made a mistake, recognize it and take responsibility that’s number one. So it’s knowledge. Yes I did something wrong and I accept that I’m here because I did something wrong. Not because I had a bad lawyer, bad judge, bad stuff. And if I didn’t do that thing wrong there were other things I did wrong, that probably qualifies me to go through the process of self-evaluation. Number two, remorse. Got to feel remorse. If you don’t feel remorse, it means the action is not done.

Number three, commitment never to do it again. Number four, is to make good that damage whatever way possible, naturally it’s possible verbally, it’s possible, whatever way it’s possible, change of habit, it’s possible. Number five, which is their re-entry test. Is to be confronted with a similar situation that you failed the first time and not then you know you’re done. But that level of teshuvah is an internalized process of work. And you can’t do that by, there’s no magic to that. As the Alter Rebbe says, there’s a long and short way, which means you got to go through it and it’s not so comfortable when you starting to feel that I act guilty, I hate what they said I did, I just have to face my own truth. I know that I’m not going to do it again and I feel badly about et cetera, et cetera, et cetera. So that’s how we were able to infuse these people with an inspiration to reach another level.

And I’ve had so many stories that if you want just a simple story. It was a Jew who was in prison for the early years of… He was in prison for breaking the codes of the various governmental offices. CIA. And he broke the codes. He was a very high level senior analyst and he was arrested because someone snitched on him. But recently he said he broke them, he never used it for his own benefit. He said he did it to show the country. So this man, brilliant guy and slowly I started to educate him. One day I asked him if he’d like to put on tefillin and he said he’s never done it before, but he did remember he says, that his grandfather would wrap his tefillin and would make him count in Hebrew, echad, shtaim, shalosh. So he remembered that. Anyway, I arranged to set up a pair of tefillin. First, he made tefillin out of cardboard… but I had actually a Reform Rabbi because it was some forlorn place that was waiting to close stuff out at that time.

So I asked the Reform Rabbi that I happened to know, the police go there and show him out and put on the tefillin, which he did.

Speaker 2:
Wow.

Sholom Lipskar:
And he started putting on the tefillin, like he was very moved by it, and he started reading voraciously. And I would send him books after books, without the covers, we had to tear off the covers to send books. And he read voraciously. At that time there were no books online, so everything… And the Chaplain there was good enough to receive it on his behalf. He read the chumash, started reading mishna. He was reading Shulchan Aruch. One day he calls me if I could do him a big favor. Since he read how important it’s to hear the shofar before Rosh Hashanah, how significant it is for every… He’d like to know if I would ask someone to hear shofar on his behalf, even though he does know that you cannot have a proxy to hear shofar for you, but he has no other choice. So he gets someone to hear the shofar on his behalf then he would make a commitment to pray for that person every day of year. So immediately I said, I’ll do it for you but better, let me see if I can help you out. And went through some hoops and were able to send a shofar nto the prison.

David Bashevkin:
Wow

Sholom Lipskar:
With a tape about how to blow. After Rosh Hashanah, the guy calls. He said, I want you to know when I heard shofar on Rosh Hashanah, the walls of prison fell away and I felt like I was connected. So that’s basically Aleph’s method of teshuvah.

David Bashevkin:
That’s an incredible story. Aleph, thank God, has been incredibly successful and has brought more and more attention to the work that your organization’s been doing. I know there’s an HBO show, it’s a big famous show on HBO called “Succession.” And “Succession” even mentioned a specific prison where a lot of Jews do it on the show they had dialogue where they were talking about this is the Jewish prison. And I’m curious, what do you say to Jews or even non-Jews who look at the work that you are doing with this population, lifting up the bottom of the building so to speak, and they see it and they say, oh they’re glorifying criminals and making the Jews who commit crimes, making them look like groise tzaddikim, like they’re so great. So I’m curious what you imagine the Rebbe would respond to people who bristle at the notion of having a Jewish prison, so to speak?

Sholom Lipskar:
Well it’s two things. Number one, I am no smarter than the Torah. I would not take a position that’s against the Torah. The mishna says, as we read Pirkei Avos, during this period of time “v’amech kulam tzaddikim,” every one of your people are righteous. He also says, “af al pi shechata Yisrael,” even though one transgresses. Hitler didn’t ask you if Jews are good or bad, if he’s observant or not observant. He just asked, if they were 25% Jewish that was all. All of a sudden we are going to become judges? don’t know who’s a good guy and who’s not a bad guy, how a person behaves is his business in his bedroom. Do we know anything? So hey, let’s not be judges. It’s very, very important. It’s number one. Number two, these people are going through so much pain and so being separated from their wives and children and in many cases dealing with real problems with the children who turn into delinquents.

And you can imagine, the sleepless nights these people have besides being in prison, having the disgrace of their name being bandied around in a negative way. The fact of the matter is, if we do kindness because it makes us feel good, this is not for you. But if we do kindness because we’re empathetic, we feel someone else’s pain, it’s a whole different issue. We don’t think of it in that way. So people who come to talk to me about that, it’s not difficult for me to cancel their discussion very quick. I don’t have that kind of judgment, it’s so important. And it’s not fair that the guy’s already being… already embarrassed, they’re already in suffering. What are you going to put do put a nail in the coffin in such a holy person? You want to make the world better? Do me a favor, make the world better by shutting your mouth and not talking lashon hara.

David Bashevkin:
Beautiful. You know, you had the zchus to interact with the Rebbe directly. We’re talking about teshuvah. I’m wondering if you could share a memory, a teaching, an interaction that stands out for you when you think of teshuvah and the Rebbe.

Sholom Lipskar:
Well, the fact of the matter is of this particular talk that the Rebbe gave, he talked about opportunity for people in prison. And at the same talk he talked about heavy responsibility of rabbis, not to be happy with the fact that they once got semicha, but to continue to learn and to be aware of things. And when we translated to these guys, they could not believe. He says, I never heard of… he’s knocking the rebbe, he’s lifting the privilege. Let’s just to tell you about teshuvah. The concept of teshuvah by the Rebbe was extremely open factor. And the Rebbe gave every single human being the benefit of the doubt in terms of where he is and what he can be. And never allowed a person’s weaknesses to weigh him down to such a degree, that he would not be able to rectify them. And each time there was a positivity about the person’s capacity and the person’s objective in the right way, rather than addressing the negatives. And without the question, the Rebbe would always say, we say “slach lanu” three times a day, right?

Forgive us, in shemona esreh, three times a day. There’s a law in hilchos brachos. “Safek brachos l’hakel.” You have a doubt that you made a bracha? You’re not to make another bracha. Here, in shacharis, he just said “slach lanu,” which means you sinned. A few hours later, mincha, you do it again and maybe 15 minutes later, guys that don’t have any time. I said, why are we doing it again? What’s the meaning of that? Because the Torah accepts the fact at each time that you reach a level of cleansing, you become more refined and as such the stain shows up. So God is constantly in a state l’hakel… you’re good instead, forgiving that God is not like a human. Make a mistake once, he’ll forgive you twice. Make it three times. But make the same mistake 20 times in a row, he’s not forgiving you. But God keeps doing the same thing over and over again for 25 years, and he still forgives you.

David Bashevkin:
Wow, beautiful. I cannot thank you enough. It really is a deep honor to speak to you, to highlight the work that you do, which is devarim haomdim b’rumo shel olam, really stands in a world because the world doesn’t see or appreciate what this population is going through. And the fact that you have highlighted this has really, I think, uplifted the rest of the building, the entire building through your work. So thank you so much Rabbi Lipskar, for taking the time to speak with me today.

Sholom Lipskar:
Thank you.

David Bashevkin:
More than anything else, what stood out to me in the conversation with Rabbi Lipskar was that beautiful imagery of how do you lift up a building? How do you lift up a building? Do you pick it up from the top? Do you take a crane and pull the building up from the top floor of the building and get it off the ground?

No, of course you don’t. You have to get a lift and lift it up from the bottom. And that’s the only way you’ll ensure that by lifting up the building, you don’t also destroy it. And I think about that in terms of society, in helping, assisting and supporting the people who at least through our eyes seem to be at the bottom. But more than that, I think about the way we lift ourselves up and that you could kind of conceive and look at your own life as a building of sorts. And how do you lift up the building that is your life? How do you lift up a family? Do you just take the best parts, the most wonderful parts and pull that up by the head and hope that the rest of the body, the rest of your life stays intact? Or do you find a way to include even the parts of your life that seem to be at the bottom, that seem to be most isolated, most dark and lift from there as well.

And I think a part of the process of teshuvah is giving us the capacity and the strength to confront even the bottom floors of the building that is our lives. To find that freedom and redemption even in those bottom floors, even in the cellars of our lives, the darkest points. And I think that’s why in many ways the introduction to the entire service of Yom Kippur is where we ask, “lehatir atzmo l’hitpalel im ha’avaryanim,” where we ask permission to pray even with those people who we call “avaryanim,” who are the kind of the boorish, lowly parts of our society. And it’s a strange way to introduce such a lofty part of davening, we don’t introduce davening like this on a regular weekday. We don’t ask permission on Shabbos to pray with the lowlives, with the bums. And maybe somebody would say, well we have to do this specifically on Yom Kippur because they’re not showing up the rest of the year.

So here is where we have to ask for permission. But another idea that I heard from my rebbe, when it comes to the Torah of teshuvah, Rabbi Yaakov Glasser, is something so moving and so beautiful that “lehatir” doesn’t just mean to ask for permission. “Lehatir” also means to untie. It also means to create, to untie those knots and create a little bit of room to be able to daven with those parts of yourself. “Lehatir atzmo l’hitpalel im ha’avaryanim,” to let go of those parts of yourself that are so ugly. That to give yourself the perspective that even from those bottom cellars, I can lift those parts of my life up. I don’t have to look at myself and I don’t have to look in the mirror and just focus and just squint enough so I only see the good things that I’m doing, that I only see the wonderful things that I’m doing.

But “lehatir atzmo l’hitpalel im ha’avaryanim,” is to untie and unburden and un-package and process all of the ugliness that remains dormant in the cellars of our lives. And allow ourselves to enter fully into the Yamim Noraim and to daven and to have the teshuvah experience. Address both the top floors and the bottom floors of our lives to give ourselves permission to enter into the teshuvah process with the totality of ourselves. So thank you so much for listening, for this podcast especially. I just want to begin by thanking our dear friends at The Aleph Institute for their help coordinating this entire episode and specifically if I can call out my dearest friend Rafi Chemel, again, whose last name I’m not sure I’m pronouncing correctly, for really helping make all of this happen.

If you want to be a part of the amazing work that The Aleph Institute does, especially in these days of din v’rachamim, days of judgment and mercy, then please head over to their website, Alephinstitute.org/donate. Where you could help The Aleph Institute continue to support and help people no matter what floor of the building of society they may be on to find freedom, mercy, and redemption in their own lives. Their work is entirely made possible by caring people just like you. And of course, thank you so much to our series sponsor Daniel and Mira Stokar for making this entire teshuvah series possible. We are so grateful for your support and friendship. This episode, like so many of our episodes was edited by our dearest friend, Denah Emerson.

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