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“You Help Criminals.”

White Collar Advice

Release Date: 01/22/2026

Michael Santos Told Me About Roman Fabrizi show art Michael Santos Told Me About Roman Fabrizi

White Collar Advice

July 9th, 2008, four or five months into my sentence, around 3:45 in the afternoon just after mail call. Michael Santos asked if I knew the new prisoner who had transferred in from another prison, about 20 feet away, loud, showing off, telling everyone there's no deal he can't close, the jets he flew on, the models he slept with. I said no. Michael said that's Roman Fabrizi. Walking the track that afternoon he told me Roman Fabrizi isn't a person, it's a type of prisoner: the one who mocks other prisoners who are willing to try and build, and who cozies up to staff hoping for a benefit, more...

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Pity Was Worse Than Any Day in Prison show art Pity Was Worse Than Any Day in Prison

White Collar Advice

I was working late with Breaking Bad on in my office, season two, episode six, and when Gretchen told Walter she feels so sorry for him I stopped and filmed this. When I was a defendant I took terrible care of myself. In-N-Out four nights a week. A thing of Red Man chewing tobacco every two days. My teeth would bleed and I wouldn't stop. I was punishing myself because I felt like I deserved it, and I got so used to the pain that I didn't even try to get better. Right after I was sentenced I played in a charity golf event at El Caballero Country Club in Tarzana, and an old friend, a retired...

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Don't Pack Anything You're Not Prepared to Lose show art Don't Pack Anything You're Not Prepared to Lose

White Collar Advice

He called 90 minutes before surrendering to the camp at Fort Dix and wanted to know what to pack. I told him the longer you stay on the wrong train, the more expensive it is to get home. He said he didn't want to talk about the train, he wanted the packing list. So here's my story. Three days before I went to prison I looked at the Taft commissary list, saw white Reebok shoes and a Timex watch, drove to Big 5, bought them, and surrendered wearing them. They told me I could donate them or send them home. I think they went to the correctional officers trust fund. Don't pack anything you're not...

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How Do I Leave Prison Better Than I Went In show art How Do I Leave Prison Better Than I Went In

White Collar Advice

A crypto executive, married with two young children, emailed me. He's going to prison for 37 months for money laundering and mail fraud, and he asked how he can leave prison better than he went in. Four things. First, what is the next right thing for you to do? The consequences of a conviction are overwhelming, and plenty of people, including him until he went to jail, never start. Maybe you want to engineer an earlier release, so begin answering that. Second, why are you going to prison? There was a breakdown, a fracture, that compelled you to go rogue, to launder money, to break the law....

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My Son Asked If Prison Was Kind of Fun show art My Son Asked If Prison Was Kind of Fun

White Collar Advice

My young son asked me if I'm happy I went to prison. I asked him why he would ask that. He said it seems like it was kind of fun. I told him I'm not happy I went, and I don't want him to go. I speak about it favorably because I learned so many valuable lessons. Here's a small one. I had a great trip in Billings, Montana, I'm flying home, and terrible weather in Denver has me delayed two hours, then another two. I'm not complaining. I'm sitting here alone listening to a Jim Rohn audiobook. I'm not standing for count. I'm not doing a fire drill at 2 a.m. When I share those details with my son...

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Start Thinking Like the Underdog You Are show art Start Thinking Like the Underdog You Are

White Collar Advice

About six months ago a former accountant who served 15 months for payroll protection fraud called me with one question: how do I disclose my felony conviction to potential employers. He didn't take the advice, because he called me today with the same problem while I'm in Montana still trying to get home. I reminded him that prison doesn't change the fact that he ran a successful business for more than 20 years and holds an undergraduate and a master's degree. He owned the conviction and accepted responsibility for it, but he isn't thinking like an underdog. Malcolm Gladwell wrote about that in...

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Matt Cox on the Fry Machine and Freedom show art Matt Cox on the Fry Machine and Freedom

White Collar Advice

Matt Cox on the guys who won't take a job because it pays a hundred dollars a day instead of 300 or 400. Work five days at a hundred and you have 500 you didn't have before. He says they would rather stay in prison than do something beneath them, and he asks what's beneath you when prison is where you already are, at the bottom. If he's working the fry machine at a fast food place, he still gets to watch YouTube, watch Netflix, turn the channel, meet a girl, order his own food. All of that is an improvement. The worst day out here is better than the best day in prison. They don't see it that...

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He Told Me His Lawyer Wouldn't Let Him show art He Told Me His Lawyer Wouldn't Let Him

White Collar Advice

A doctor back east called me. I spoke with him about nine months ago and he told me his lawyer wouldn't let him do the work. I said he could have a different conversation and try to engineer something different. He said no, he won't let me. So now he has a probation interview that isn't correct, a sentencing memorandum he never reviewed, and the longer sentence he absolutely knew was coming, and he's blaming everybody else. The lawyer is an opponent. The prosecutor is an opponent. The judge is an opponent. I told him how he gets back on track, and telling people what they don't want to hear...

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Instagram Followers Don't Make You a Lawyer show art Instagram Followers Don't Make You a Lawyer

White Collar Advice

I'd rather be in prison than on a fast boat in the ocean, but my kids love it and I love my kids. When I got off the boat in the Bahamas I had a kind text from a guy who scheduled a call with me for Monday. He asked me to review his indictment and his potential plea agreement before we talk. I won't, and here's why. A consultant in Florida who has been to prison twice told someone he might as well go to trial, because if he loses the sentence is the same either way. That guy got nine or 10 years. Another guy, apparently because he has some followers on Instagram, told a doctor to take the deal...

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What Chipper Told My Best Friend Over a Drink show art What Chipper Told My Best Friend Over a Drink

White Collar Advice

I saw Chipper Jones at dinner in the Bahamas and it took me back to 1999. I'm not comparing myself to a Hall of Famer, the second greatest switch hitter of all time behind Mickey Mantle, but it shows what one conversation can do. My best friend Brad Fulmer, who came to my sentencing hearing and visited me twice a month in prison, was in his second year with the Montreal Expos. He finished third or fourth in Rookie of the Year voting the year before, then got off to a bad start and felt the manager wasn't a fan and wouldn't play him against lefties. I was in Montreal watching the Braves play...

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More Episodes

After my daughter’s basketball game, someone pulled me aside and said I work with “criminals.” Years ago, I would’ve argued. Now I listen. Before prison, I would’ve said the same thing. A DOJ press release tells one side. That’s it.

I asked him how he saw me—as a father, a husband. Then I asked how he would’ve seen me 20 years ago reading my indictment. The answer was obvious. People aren’t frozen at their worst moment. I’ve watched men rebuild after creating their own crisis. I’m proud to call them friends.

Judges—formal or informal—should look at the record being built today, not headlines from the past.
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