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Show Notes:

308 Jeff Grant

Co-Founder of Progressive Prison Ministries

“I was dressed up looking the part, but deep inside, I was just vacant. I just was not someone I was proud of anymore.”

Jeff Grant, J.D., M.Div. is Co-Founder of Progressive Prison Ministries, Inc., the world’s first ministry serving the white collar justice community. Jeff co-hosts with Babz Rawls Ivy the Criminal Justice Insider podcast and hosts the White Collar Week podcast. He also leads a weekly online confidential White Collar Support Group.

Twitter: @RevJeffGrant


Nadia Bolz-Weber:

When I was in seminary, an older pastor said “Nadia I’ve seen you around for a few years now…and you give off a lot of strength – I think that’s what people see when they look at you, which is great. But… what is it we don’t see”

That was about the rudest question I’ve ever been asked.

But I answered as honestly as I could; “I get my feelings hurt more than anyone would suspect” I replied. Which is true, but only a partial truth.

I’ve found myself asking a form of that question a lot. What’s the thing under the thing? A question which has led me to understand, even if just a little bit, how shame really operates in our lives. 

Because it can feel as though shame can be like a quill that writes its own story inside of our bodies, a story that tries to tell us who we are, and what we are worth. A story that keeps us moving in the same unhelpful direction just because its familiar, and just because we’re scared.

And I used to think that the people who struggled with shame were the ones who wear that story like a name tag – letting the world know that they are who their shame says they are, the ones slouched over with trauma and wounds and a diminished self.

But I’ve started to see that others of us are equally defined by shame –  we just carry it in opposite ways – we spool all our energy into trying to prove our internal story wrong, we cover the truth of what we don’t want to admit to with bravado and confidence and grandiosity and hope no one notices. 

Because the deeper truth to the question that Pastor asked me is that my youthful swagger was protective – it was brilliantly strategic. My confident posture hides the fact that, despite how my life looks on the outside, I still can feel like that skinny big eyed kid who was chronically sick and spent years sitting by herself at middle school lunch tables. 

Shame is such a powerful driving force that if harnessed, I’m pretty sure it could replace fossil fuels.

I’m Nadia Bolz-weber and you’ve stepped into the Confessional, it’s like a carwash for our shame and secrets. Stay with us.

NBW: My name is Nadia Bolz-Weber and you have stepped into The Confessional. Joining me today is Reverend Jeff Grant. I’m delighted to have him with me in The Confessional. I can’t wait to hear your story. Welcome, Jeff.

Reverend Jeff Grant: Thanks for having me here, Nadia.

NBW: Set the scene for me, tell me what was going on in your life that led up to the moment you want to describe.

JG: I think the word that comes to mind is grandiosity. My family and I went on vacation, probably five times a year. It was always the same. There was no backpacking or skiing for us, we went shopping. We would fly out to Los Angeles and stay in the Chateau Marmont and to rub elbows with the stars that were staying there. I remember, once we were at this store that’s pretty well known. We were just spending a ton of money. and at the time, I was probably high on three or four tabs of Demerol.

The young women who worked there were just paying me with scotch. My ex wife and my kids were just picking out whatever they wanted and they just piled it up on my lap. I fell asleep in the chair and when I woke up from passing out, the clothes on my lap were over the top of my head. I was just a prop. I pulled out my black American Express card because that’s what I thought people were supposed to do, and paid for everything. We left with shopping bags worth of clothes, This was our life. There was never a day that there weren’t shopping bags and new acquisitions. It was a sickness. It was something that we took pride in, in this sick way.

NBW: Were you raised in a wealthy family, or was there a novelty to it for you? 

JG: We were raised in a Jewish ghetto, on Long Island. This was the swinging ’50s, and swinging ’60s and my parents were into all kinds of crazy stuff that people were into back then.

Mostly what they were into was ignoring their children. I lived in a neighborhood of parents that were absent. We raised ourselves and we did a pretty bad job of it in a lot of ways. We didn’t really grow up with any character or ethics. We were alone, so we created rules, and we learned rules, and we developed this arrogance that didn’t serve us, certainly didn’t serve me later in life. This contempt for authority was pervasive all through my childhood and then when I went to school, and ultimately when I became a lawyer

NBW: What was your law practice like? 

I had a good practice, successful.. I had about 20 people working for me.  and I owned a bistro that was in the neighborhood.

NBW: What kind?

JG: It was a new American restaurant, a bistro, it had 36 seats. 

and the reason I opened the restaurant was to meet clients, and I met them. 

I was a backslapping, good old boy kind of guy, who people liked, I think, but everybody likes to know the owner of a restaurant. I would go over to their table and schmooze with them.

And I became the general counsel to some major real estate companies. and the money was flowing and the spending was flowing. 

NBW: When I hear you describing being this successful owning businesses, being an important fixture in the community, the money’s flowing, the spending’s flowing. That  sounds like you were living the dream , but what was the reality?

JG: I think it was living the dream but the problem is that it had its dark side and that was the anxiety of having to always have more and to grow way beyond my comfort zone. My payroll was about $125,000 a month, which means I had to make $1.5 million a year just to pay the over-heard. The weight of that was just crushing. I thought I could solve problems by becoming bigger. It never even dawned on me that the way I could solve personal problems or business problems was to become smaller, to simplify life. 

The more things ramped up and the more complicated they became, the more I turned to drugs.

I had doctor friends who kept prescribing and I kept manipulating them into it.

NBW: Can you describe that manipulation?

JG: Sure. Mostly, it was because I was the lawyer in this group of people and I held all their secrets.  Everybody wanted my time, but not to pay for it if they could avoid it. What I did was I traded my time for drugs. I lived this double life where I was a great dad and family man and I own restaurants and real estate and parts of health clubs and things like that. Every night, I was stoned out of my mind.

I had a client who had broken his neck and so he had an unlimited supply of Oxycontin. He walked into my office one day, I guess he knew that I was taking prescription opioids at the time. He just opened up his hand and he dropped the pile of Oxycontin on my desk.

He said, “I think you might like this.” Once I started the Oxycontin, there was no turning back. In fact, I couldn’t even go to work. I spent afternoons sitting in his house, watching the golf channel with him. 

NBW: So What happened? 

JG: What happened was I stopped being able to show up to work regularly. I was just too out of it, I was too stoned.

The day came when we ran out of money in the law firm. 

You just can’t not show up at your business for a year or so and expect it to be healthy

my office manager had come into my office and told me that we weren’t going to be able to make payroll. That I had to come up with some money. I remember just feeling desperate. What was I going to do? 

I said to her, “How much money is in the escrow account?” She looked at me like, “What are you doing?” I said, “We’re going to borrow some money from the escrow account.” 

At any given time, we had several million dollars in escrow sitting there that was client’s money, that was meant to be transferred to clients for the sales of their houses, or sales of their building, or sales of their businesses. 

I had no money in my operating account and to transfer the money from the escrow account to the operating account was just two pushes of a button on a computer. I thought that I would borrow it and pay it right back, which is I guess, the great lie of everybody who gets involved in these things. 

She checked me and she said, “Are you sure this is what you want to do?” I said, “Yes,” and I felt nauseated. I knew that it was wrong but on some level underneath I also knew that it was absolute and utter destruction. And that I didn’t have the character to do what really needed to get done. 

 I could’ve called my banker, that would’ve been sane. I could’ve called a friend,  

I was just not able to do it because I was just so full of shame. instead what I did was I invaded the client escrow account and I took my client’s money. `

NBW: What did that voice of shame– What was it saying?

JG: It was telling me that I was that fat kid from first grade who got picked on. I was the kid who would sit in my room and cry when my parents were screaming at each other.

There I was all alone. There was nothing I had. I had an empty well. I had nothing in reserve. Nothing.

NBW: You made this choice to take money out of the escrow account … and it made you sick to do it, but then did it keep feeling that way every other time you did it?

JG: I think the answer to that is yes, but I became increasingly numb. Less guilty, but more shamed, was feeling shame in everything. I was dressed up looking the part, but deep inside, I was just vacant. I just was not someone I was proud of anymore. The reasons I had become a lawyer, the initial goal to help people, I wasn’t helping anyone anymore. I was just trying to make enough money to survive. 

It wasn’t long after that, that there was an investigation into my finances by the grievance committee of the bar…and we fought it for over two years.

Once the investigation started and I was compounding the lying that were depositions and I was lying through the depositions, because what choice did I have? I was living a lie and I probably believed the lie in a lot of ways

During those two years was 9/11. That really threw me for a loop. It’s like it is right now in COVID. The world was spinning out of control. There were advertisements on TV and on the radio for businesses that were in economic distress to borrow money from the Small Business Administration, just like there are now. I applied for an SBA loan but I lied on the application and said I had an office about a block from ground zero. 

They lent me the money, $247,000 but it didn’t do anything to save my firm because my firm was heading down.

I took most of the money and I repaid personal credit cards that I had run up trying to save the business. That was money laundering. That was a violation of the terms of the loan. I think a lot of people are probably doing that right now. The lesson I learned was that you can’t save your business and your lifestyle at the time. 

One day in July of 2002, I couldn’t handle it anymore. The news was just not good in terms of trying to save my business. I called up my ethics attorney and told him to resign my law license for me. I’ve got one last prescription from a doctor friend.  AndI went home that night. After my wife and kids went to bed, I took 40 tabs of Demerol and tried to kill myself.

NBW: It’s amazing, you’re alive. It’s astounding. 

JG: It didn’t kill me—

I wound up going through detox and then seven weeks in rehab. 

When I came out of rehab, I went to my first recovery meeting. That was eighteen and a half years ago. After 9,000 meetings, I’ve never touched another drug or drink since.

I was sober for about 20 months, and I was going to three meetings a day to recover. I got a phone call from a federal agent, who told me that there was a warrant out for my arrest in connection with the misrepresentations I’d made on that loan.  I knew that I was cornered. 

Two weeks later, I appeared at the US courthouse in Downtown Manhattan and turned myself into the US marshals. Downtown Manhattan then was still like a war zone, post 9/11. There were checkpoints and barricades and military outside of buildings with machine guns. I felt like the biggest criminal in the world. I knew that I had taken advantage of a national emergency and had profited from it by borrowing this money. 

NBW: Jeff, it strikes me that at the beginning you talked about how it never dawned on you that you could solve your problems by getting smaller, or asking for help – that like, the grandiosity you inhabited in this life you built drove you to keep going in the same direction that was destroying you.

But you also started out by telling me about your wife and kids – what happened there?

JG: My wife had had it with me already. When the time came that I got arrested, I guess that was the last straw. She threw me out. Any money I had, I dedicated to paying for her and my kids’ rent and overhead. I couch-surfed for two years waiting to go to prison.

NBW: You went from high-end retail vacation, having all the luxury goods piled up and paying for them, to you covering their basic expenses and sleeping on people’s sofas.

JG: Yes. That was pretty much the case right up to when I went to prison in 2006.

NBW: Wow. Tell me about going to prison.

JG: On Easter Sunday of 2006, I reported to Allenwood low-security correctional institution in White Deer, Pennsylvania.

On that compound of 1,500 men. There were five former stockbrokers. There was one former lawyer that was me and there were two former doctors and basically 1,500 drug dealers. For the next 13 and a half months, I learned how to navigate life in a prison of people who– the type of person I had never really met in my life.

I learned incredible life lessons while I was in prison about respect and dignity and humility and character. I met some of the most fascinating, interesting, intelligent people I’d ever met in my life. 

NBW: You know what just kind of dawns on me is when you were describing your childhood, you were like, “We had to parent ourselves and we weren’t good at it. There was no one there to teach us about character and responsibility.” You literally just described that you finally learned those things from drug dealers in prison.

JG: Yes. I’m getting the chills. You just telling me that, but that’s true. I knew nothing about how to treat other people. I knew nothing about how to treat myself. When I came out of prison I was different. My motivations were different, the things I cared about were different, I was broken, I was softer, I was gentler, I started to volunteer.

I volunteered in drug rehabs and in residential criminal justice organizations until the day came when I didn’t really know what I was going to do and I went to the pastor of the church that I had been going to and I tried to describe to him that I want to live a life of service, but I don’t know what that means. He said to me I think you should consider going to seminary.

NBW: It’s a sucker punch.

JG: Yes. I had no idea what that meant.

NBW: That’s probably the only reason you agreed to go. 

JG: I thought a seminary was where monks walked around in robes.

NBW: Sure.

JG: I didn’t know. He explained to me that a progressive seminary was really a place to learn about social justice. I applied to Union Theological Seminary in New York City. 

It was the first time I’d ever told my story anywhere. I had to write it in my application

NBW: What’d that feel like?

JG: It was horrifying. It was the most frightening thing I could imagine. It probably felt more frightening than going to prison because I had to tell the truth.

NBW: Yikes

JG: I was as surprised as I could be when I got the letter in the mail that I was accepted to seminary and it wasn’t easy.

It was also a time when all the students were involved in Occupy Wall Street, and they were down fighting against the one-percenters and I had been a one-percenter., They didn’t know what to make of me, but I learned about the underground economy, and I learned about showing up for people because it was the right thing to do not because they could afford my services, for example.

NBW: Can you tell me who and what did you harm through the crimes that you committed?

JG: It took me probably 10 years or more to recognize that I hurt anybody. It was only when working with other men who had been through similar circumstances and counseling them that I was able to talk to them about the wreckage that they had caused and then finally recognize in me that I did that too. That I’d hurt my ex wife, I hurt my children, I hurt my community, I hurt all the people who were dependent upon me, I hurt my clients. I hurt the fabric of the profession that I made my living in that I hurt people’s ability to trust lawyers.

NBW: Jeff, can you name what it is that prevented you from seeing that? You just had a long list there, what kept you from seeing the fact that you had caused that kind of harm?

JG: I think that primarily, it was self pity, and also, it was the only way I knew how to cope. I had to compartmentalize. It was unbearable to look backwards.

NBW: It’s amazing to me how often our coping mechanisms involve some sort of mental gymnastics we have to perform in order to justify our behavior – where we basically just cant let in competing information about ourselves

JG: Later on, I asked friends,  “You must’ve seen I was crazy, that I was acting crazy, that I was on drugs. Why didn’t you ever say anything?” They all said, “We did say things. We all told you that you needed help. You just couldn’t hear us.” 

NBW: How many of us have those people in our friends and family groups, who we see them spinning out and we’re totally powerless. We do the brave thing of confronting them or saying something or going like, “This isn’t okay, and you need help.” They have a million justifications for why they’re actually fine and you’re wrong.

JG: Exactly.

NBW: The guilt that so many people carry because they can’t help this person in their life. 

NBW: Jeff, Before we go, I’d love to hear about the work you do now.

JG: I met a woman in recovery who later became my wife and We decided to start a ministry to support white collar criminals and their families.  No one had ever done it. There’s so much stigma and shame and schadenfreude for these people who – their families have been destroyed and they can’t get jobs and they’re facing prison sentences or they’ve come home from prison.

JG: And If I sit down with someone who has been prosecuted for a white collar crime and we meet in a diner, for example, and we sit down, and he doesn’t know that I’m gauging him from the minute that we shake hands.If he’s wearing a $50,000 watch, I already know that that’s what he’s using to hide behind. There is so much shame there. There’s so much that he can’t talk about. There he is, with his arms folded in front of him and using that watch as a shield. 

NBW: That’s extraordinary. I love that this is the work that you do. It’s just incredible.. where are you at with self-forgiveness? 

JG: I would love to be able to tell you that I’ve forgiven myself but it’s so different than feeling like I’ve been forgiven. Because in my heart, I really do feel like I’ve been forgiven. Whether that’s Jesus or God or just the universe has opened up again so that it’s allowed me to feel like a whole person maybe for the first time in my life. I honestly do feel forgiven. Do I forgive myself? Maybe on a good day. It’s fleeting but I do get to experience it every once in a while.

NBW: I guess sometimes for myself when I don’t feel that self-forgiveness, I just have to rely on redemption. I feel redeemed. A lot of my mistakes or my f ailings have gone through some fucking spiritual dishwasher and are to be useful for other people. It wasn’t all for naught. The end sum is more than just the harm that was caused, that there has been good that’s come out of it, and sometimes I just have to lean on that.

Well, I’m really grateful for you sharing your story and I just absolutely love the work that you do in the world. It just feels subversive in the most spiritual sense of the word. You know? [chuckling]

JG: Yeah.

NBW: Well, keep doing it, friend. Glad you’re out in the world.


A blessing for Jeff:


You mentioned that when you stole your clients money, you felt like the scared boy who sat crying just one room over from screaming adults, the kid who was empty and had nothing.  The fat kid in 1st grade, you said.

Shame does this to us, that asshole slaps its name tag on us and says “this is who you really are.”

As if you are that terrible thing your dad used to say to you, or you are your diagnosis or you are your trauma.

So, if that happens to you again Jeff, you should know that you can try and pull off the name tag but the sticky ness, it kind of stays, it collects lint and cat hair and refuses to go away entirely, so you can pick at it, or try and hide it or pretend it’s supposed to be there – or you can just change your damn shirt.

That’s my blessing for you, friend –  

May you reject the premise of the shame.

Because he doesn’t know what he’s talking about. 

That scared crying kid need not be hidden, or denied, or loathed – he became a lawyer, built a business, made some huge mistakes and then went on to survive addiction and suicidality and prison, and now he helps others get through really horrific shit. That ignored, lonely scared kid – may you befriend him, love him, and be so proud of him. I mean, look who he’s become. 

May you Look at him in the light of the truth,  and forgiveness and see him as what he is, which is: 




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