I never paid much attention to America’s criminal justice system until I, unexpectedly, got into serious trouble. Being labeled a criminal felt to me as unlikely as someone finding Kool-Aid on Jupiter. I was the rarest of things, an honest dealer among the myriad elegant sharks and scumbags in the very prestigious realm of high-end art sales. Or so I thought. But desperate to keep my gallery afloat, I had to juggle some money and payments. I began lying about my receivables, paying Paul while putting off Peter—until I couldn’t pay him either. This was unsustainable and, it turned out, illegal. My assistant and my business partner lawyered up, distanced themselves from me, and ratted me out. I was arrested, charged, convicted of wire fraud, and sentenced to 18 months in a minimum-security federal prison.

As another convicted felon, former President Donald Trump, has pointed out, America has a two-tiered justice system. Trump just refuses to publicly acknowledge what that really means and the fact that he’s in the top bunk, so to speak. But should he lose and end up serving time, there’s a good chance that my experience might shed light on what he would be likely to face. You see, as scary as it is to be prosecuted, my experience was a dream compared to the plight of some others I knew.

I wrote this story to dispel certain myths, but also to give you an idea of what a white-collar prosecution and incarceration is like and how much of one’s experience hinges on wealth and connections, both of which Trump has in spades. As a billionaire ex-president, the strings he could pull would be far more influential than those of a merely well-connected art dealer from New York. But whatever strings exist, they matter—a lot.

Having the cash to hire a good lawyer, and not having to rely on an overburdened public defender, is the first step toward a better outcome. As you know, it often seems as though a lawyer has a professional obligation to fight harder for a client who is paying a ton of money. But what you may not know is that the conditions of your incarceration also depend, often quite a bit, on your position in the financial and social hierarchy. And the horrific Hollywood depictions of prison life for people who are not wealthy and connected can be pretty close to the mark. Consider this snippet from a Marshall Project report on conditions at an Illinois penitentiary:

In stories that echoed with the same visceral details, dozens of men said they lived under the pressing threat of violence from cellmates as well as brutality at the hands of staff. Specifically, many men reported being shackled in cuffs so tight they left scars, or being “four-pointed” and chained by each limb to a bed for hours, far beyond what happens at other prisons and in violation of [Bureau of Prisons] policy and federal regulations.

Let’s just say that nothing like that ever happened to me. Yet just because I had it easier—easy even—doesn’t mean that incarceration isn’t life altering. Being a member of the elite (more or less) and enjoying some privilege (more or less) won’t save you from the consequences of a not-so-bad incarceration. Notably, your family, career, and social standing are generally ruined forever. Your relationships that survive may end up stronger, but many will wither and die. And if you think you will ever reach the pinnacle of whatever it was you did before you went away, well, you won’t.

I know what I’m talking about.

“Do you want good news or bad news?” my no-nonsense criminal attorney, Danny Parker, asked me one bleak morning in December 2017. The weather may have been beautiful, but all days felt bleak then. At least Danny gave me an option. His news was normally just bad.

“Bad news first,” I replied. “Always.”

“There’s a warrant out for your arrest,” he said.

I struggled to breathe. I hadn’t thought this would happen so soon, even though I’d known I was in serious trouble for about a month and a half. But the justice system works in secrecy, and as I quickly learned, you never know what’s coming.

“The good news: It’s federal.”

Until that moment, I was ignorant as to the vagaries of the criminal justice system. As it turns out, the state system is more chaotic, a bit cruder, and uneven. There are 50 disparate jurisdictions, each with its own rules, characters, and, let’s call it, charm. The Bureau of Prisons tends to be better funded than state prison systems. It also has clearer standards and is a bit more humane. And the federal system prosecutes far fewer criminals than the states do overall—about 10 percent of the total. So in a perverse way, it’s a more exclusive social group.

The prisons themselves, though still awful, are generally less so than state and private prisons. At the state level, prisoners tend to have more options for getting sentences reduced, but the federal facilities are safer and their inmates less violent. Also, the food is better.

If I were to be found guilty—and I was guilty—I would likely serve my time in a minimum-security camp. Federal security classifications range from minimum (think Trump lieutenant Peter Navarro) to supermax (El Chapo). Only about 15 percent of federal prisoners end up in minimum security. But landing in one of the nicer facilities, like Otisville or Pensacola, is exceedingly difficult. As with exclusive Ivy League schools, it usually requires hiring a consultant who can lobby public officials to improve your odds of admission.

Shocked? I sure was. I learned from my lawyers that these consultants, much like college counselors, also advise prospective, uh, freshmen on which campus would suit them best. (This applies only to nonviolent criminals. If you’re a murderer or serial rapist, all bets are off.) Once you narrow down your list of prospective prison camps, like Tom Wambsgans in Succession, your consultants pull strings to try to get you your preferred choice. And once you’re accepted, they’ll advise you on what to expect.

When it became clear I would be doing time, I called prison consultant Joel Sickler, who boasts an 80 percent success rate in landing people the facility of their choice. Given my level and type of offense (felony, wire fraud), he was confident he could get me into Otisville—which we, the cognoscenti, call OTV. Roughly half of its clientele consists of white-collar criminals: disgraced executives, unscrupulous lawyers, careless politicians, and wayward rabbis. Most of the rest are in for more serious offenses, like nonviolent drug crimes, or because good behavior at a higher-security facility earned them an upgrade. Otisville is the clubbiest of Club Feds, the Harvard of the Catskills, the yeshiva of misconduct. The best possible option for the worst part of your life.

Otisville is the clubbiest of Club Feds, the Harvard of the Catskills, the yeshiva of misconduct. The best possible option for the worst part of your life.

It likely helped that I’m Jewish because OTV is viewed as the Jewish prison. For years, advocacy groups had lobbied federal officials to develop a lockup with accommodations for religiously conservative Jews. As such, Otisville has a real Torah, a kosher kitchen, and a huge Hebrew library. It makes accommodations for the High Holidays. (I’m basically an atheist, but I would take all the help I could get.) You’d have to be a fool, Sickler told me, to cause trouble and get yourself transferred out of this promised land. “Keep your head down and don’t mess around,” he advised.

But before you book a stay, let me dispel your preconceived notions about Club Fed’s reputation for being cushy and how white-collar felons get undue perks. Much of that is exaggerated. Maybe it sounds better than that cruise you took with your in-laws, but minimum-security prison is still prison. I figured that much out pretty quickly.

Danny called me into his office one day for a horrible conversation. The US attorney was offering a deal, he informed me. If I admitted to my crimes, which are not uncommon, as I once wrote, in my profession, I could expect a lenient sentence: 51 to 63 months—4¼ to 5¼ years! He then gave me the best legal advice I’ve ever received: Take the deal without counteroffers or complaints.

This is the dirty little secret of the federal system: Once indicted, you will almost certainly lose. Plead guilty should you ever find yourself in such a mess. I know many people who tried to fight, and they all got longer sentences. Guilty or innocent, you’re fucked at that point, so you might as well accept your fate. My only consolation was that I knew I was guilty and had no desire to pretend otherwise.

After carefully researching the various bridges in downtown Manhattan—they’re all about the same height, turns out—I drew up a list of “mitigating factors” to convince the court I was still basically a good guy despite my monumental fuckup. I stressed my remorse and said I would take my punishment like a man. For this, the judge rewarded me.

Sentencing took place in 2018, on a Thursday in September, and the judge put me away for 18 months. Two weeks later, I received my assignment in the mail: I was to self-surrender at Otisville on the last day of November. (I got in! I got in!) This gave me ample time to put my affairs in order.

I couldn’t believe my luck.

To enter Otisville, you first pass through the adjacent medium-security prison. Here, the guards questioned me about every aspect of my life and then led me into a small room with shelves containing uniforms, either green or tan. “What’s your waist?” a guard asked. He then instructed me to take off my clothes and put them in a bin nearby. I had heard about this part: the strip search. I would get used to it eventually.

Front. Back. Squat. Cough. Lift your right foot. Now your left. Turn back around.

“Up,” he said, and, when I looked puzzled, he motioned to my groin. I lifted my scrotum.

“Okay,” he tossed me a green uniform. When I pointed out the pants were loose, he assured me: “You’ll get a new uniform. Don’t worry.”

After my fingerprinting and a mug shot, the officer was joined by another guard. Rosado was loud and funny and perhaps a bit scary. He locked me up in an actual cell for several hours before giving me a bedroll, taking me out to the quiet parking lot, and pointing to the top of a winding road, where I would meet my new friends.

“This is weird,” I thought as I walked, unaccompanied, up the hill.

The camp at Otisville is very different from the prison it surrounds—a spartan enclave in the mountains of upstate New York. There are only two buildings. One is a dormitory that houses 100 men in a maze of 50 cubicles with 6-foot-tall cinderblock walls. No doors. Each two-man cubicle contains a metal bunk bed, two metal cabinets, and two plastic stools. The smaller administration building has offices for the “counselor,” who oversees the camp, and the case manager, who advises and advocates for inmates. It also has classrooms, a chapel, a dorm for 20 more men, and a visiting room with all the charm of a Greyhound terminal. One of the former inmates I’d spoken with in advance captured the vibe perfectly: “It’s like going to a shitty summer camp in the ’70s—in Alabama.”

“It’s like going to a shitty summer camp in the ’70s—in Alabama.”

Walking into the dormitory for the first time, I was full of trepidation. In the movies, the new guy is always a target. But when I entered my 8-by-9-foot cube—home for the next several months—I was immediately welcomed by several mild-mannered, middle-aged guys. They gave me a toothbrush, toothpaste, deodorant, and even new shoes. I arrived with nothing, and they gave me everything I needed. It was a Friday evening. Within an hour, I found myself at a full-fledged Shabbat service and dinner, replete with prayer books, brisket, and babka. Mickey, the de facto head of Otisville’s Jewish community, gave the following speech:

“As we know, this is the Sabbath of Unity. We are all reminded that in here, we are brothers, united in our shared experience. No matter how religious anyone is or from what background, we are all Jews. The Jews of Otisville…welcome to the Sabbath of Unity.”

Where the fuck am I?

Waking up at OTV for the first time was weirdly serene. There was barely any schedule and little to do, but also little to fear. I witnessed no violence during my time there. The camp is small, and with everyone in our green uniforms, it felt like being in the Army, only without drills and commanding officers. There’s neither reveille in the morning nor a specified bedtime. You can watch TV all night, play cards, or hang out and talk. I realized I’d be having plenty of interesting conversations, as I had in the dorms back in college.

I was genuinely shocked by how accomplished, educated, intelligent, and, dare I say, normal nearly everybody was—a far cry from the cartoon villains I’d imagined. Most of the prisoners were simply average (or above-average) men who’d screwed up, misjudged, gotten too ambitious or desperate, and were turned in by someone they trusted. Just like me!

The only major drama was the occasional abrupt shakedown, during which staffers would kick us out of the buildings and rifle through our belongings, looking for drugs, booze, cellphones, and other contraband. These raids usually followed a tip that someone had brought something in, like Billy McFarland of Fyre Festival infamy, who smuggled in a phone and a recording device—stupid transgressions that led to me and some others getting strip-searched again. Spoiler alert: None of us had an iPhone up his butt.

But mostly, we just wiled away our days doing the mindless “jobs” we were assigned; working out; and playing chess, poker, Scrabble, or tennis. There was lots of free time to talk, laugh, and bond. If Trump loses the election and eventually lands at Otisville or a comparable place, I can predict how his bluster might be received. Prison, even pampered prison, is a great equalizer. The uniforms, the demeaning jobs like cleaning toilets, the standing up to be counted several times a day, the inane “programming”—one class was called “Doing Time With the Right Mind”—strip away one’s individuality and dignity. Whatever fame or fortune you had in real life means little here. As your fellow inmates will tell you, “In here, you’re no better than me.”

That sentiment was expressed to the likes of former Trump fixer Michael Cohen (in for tax evasion, making false statements, campaign finance violations), Jersey Shore’s The Situation (tax evasion), and former New York state Sen. Dean Skelos (bribery, extortion, corruption). All of them managed to check their egos at the gate. Could Trump? A prisoner who acts as though he deserves special treatment tests the patience of his peers. And running afoul of their expectations can make for an isolating experience.

Thriving at a place like Otisville also requires a very non-Trumpian trait: selflessness. Inmates, despite their meager possessions, are usually quick to share their coffee hoard or shaving cream with peers who have run out. Commissary comes but once a week, and strict spending limits guarantee that everyone will be short of something at some point. There are also small indulgences from the outside that get shared on the inside—books and magazines are traded frequently; Cohen would give me his “cryptic” crossword from the Financial Times. Then there’s the shared intellectual property, knowledge, and expertise, and the legal, financial, or personal advice, whether good or not. Nobody expects anything in return. In fact, the long stretches of idleness and the need to coexist peacefully means that most of the guys look forward to helping a fellow inmate. Could Trump manage that?

He’d have to learn.

An age-old question about penal systems is whether they are designed to rehabilitate or simply to punish. America focuses on the latter. Formal punishment at Otisville ranges from relatively benign (cleaning the latrines) to harsh (a stint in the “Special Housing Unit,” or SHU, a.k.a. solitary confinement). But a big part of the punishment at any prison, even OTV, is the crushing boredom. Every inmate faces an immediate and severe demotion of self-worth and confidence. By the time you enter, you’ve lost everything you most value. Minimum-security prison may be a respite from the ferocity of prosecution, but once you’re in, boredom becomes your enemy.

The most insidious epidemic in prison—though I got out before Covid hit—is mental illness. Most of the inmates I knew seemed to experience almost constant depression and despair. In many cases, their pre-prosecution lives were filled with substance abuse, anxiety, paranoia, OCD, ADHD, and other mental issues that contributed to their extreme behavior. I don’t know, for instance, what might cause a successful financial adviser to gamble away tens of millions of dollars of his clients’ money, but it can’t be psychologically healthy. According to the New York State Bar Association, an estimated 70 percent of incarcerated people show symptoms of mental illness, and up to 1 in 3 have serious diagnoses such as bipolar disorder or schizophrenia. The comparable figure for the free world is about 1 in 10.

I reached out to Lauren Brinkley-Rubinstein, an associate professor of population health sciences at Duke University who focuses on incarceration, to ask about this. Given our insufficient public investment, “who ends up treating mental health? Well, jails and then prisons, primarily,” she told me. “Because there are no community alternatives. It’s a sort of perfect storm of people who are under-resourced and then traumatizing them further.”

“Who ends up treating mental health? Well, jails and then prisons, primarily. Because there are no community alternatives. It’s a sort of perfect storm of people who are under-resourced and then traumatizing them further.”

Even OTV’s most noteworthy inmates—formerly hotshot lawyers, esteemed doctors, and titans of industry—struggled with their alienation from society. If you thought Club Fed would offer adequate psychological support, think again. There were no therapists on hand beyond the one who managed care for the broader facility, including the medium-security prison, and she was rarely at the camp. Even accessing our prescriptions was a challenge. I had to lobby hard for my Wellbutrin after the medical team initially refused to give me my prescribed dose. When the doctor asked what I thought would happen if I switched meds, I replied, “suicide,” which apparently was enough of a magic word to change their stance.

One antidote to the boredom, however, was the revolving door of new enrollees. Before Trump pardoned him, his disgraced former campaign manager Paul Manafort did some time in a Otisville-esque facility in Pennsylvania. Trump adviser Steve Bannon, ineligible for minimum-security status on account of a superseding state fraud indictment, was just released from Danbury, a decidedly harsher low-security federal institution in Connecticut. Trump’s loyal accountant Allen Weisselberg was in the unenviable position of doing state time at Rikers Island, but with two sentences that didn’t even add up to a year, he survived. Trump himself could wind up in Otisville one day if convicted of federal crimes, but I hope not.

We have our standards.

I hereby interrupt this story to offer a quick cheat sheet of my own selected wisdom for indicted Trump officials and others who end up serving time—even at Club Fed:

• Time flies: Your days will seem to drag on forever, but the months and years move fast. And both for the same reason: Nothing much happens in prison. After a while, time becomes irrelevant. One new year blends into the next, and though you don’t feel it, you can sense the time zooming by and leaving you and your fellow inmates behind.
• Everyone hates a rat. Yes, just like on TV.
• Don’t expect any privacy: With more than 100 guys under one roof, there’s a good chance someone is watching you all the time.
• Remorse either: The idea that contrition will miraculously appear for those who sit and think deeply about the crimes they committed is just not a thing. When prisoners ponder their actions, it is usually to justify them. Admitting one’s faults is not only difficult but unnatural. People can’t walk around all day believing they are assholes. Denial, minimization, pride, and forgetfulness are essential to moving on. The rare person, like me, who is remorseful in prison probably came in that way.
• Enablers are everywhere: “It’s not like you killed anyone,” is a reassuring sentiment I heard a million times at Otisville. But I brushed it off. Because it was guilt and remorse that liberated me from the bitter feeling that I got screwed by the system. Blaming myself actually made me feel better.
• America needs to make its prisons less hellish. The relatively humane conditions at OTV should be much closer to the norm. We were all appalled when Vladimir Putin treated Russian opposition leader Alexei Navalny so harshly in prison. Are we so far behind? People who commit crimes are still human, and they need a modicum of dignity. Some of them offered no mercy to their victims, so they don’t deserve any, the logic goes. But do we really want to be as bad as the bad guys at their worst?

Now back to the story.

Perhaps the most surprising thing I learned at OTV was that prison can catalyze a positive change in a person’s life. After a period of adjustment, including plenty of self-flagellation and disbelief at my stupidity, something began to shift. Nothing spiritual, but rather, I felt unexpectedly motivated by the trauma of confinement. I began writing, dreaming, making friends, and having deep conversations. I read all the books I’d previously only pretended to have read, got myself fit, and laughed my ass off. I later found out I was experiencing a phenomenon called post-traumatic growth (PTG) that was identified in the 1990s by psychologists Richard Tedeschi and Lawrence Calhoun and which psychologists and behavioral scientists have analyzed in depth.

PTG is experienced by a small percentage of people who endure something awful and unforeseen. Just as an actor might repurpose stage fright into the energy needed to perform, a person with PTG uses trauma to become a better and more productive person.

Lucky, right?

You bet. Now that I’m out, I am as happy as I was as a child. I’m less interested in money or success and more interested in just reducing stress and being with my girlfriend, kids, and friends—the real ones, not the jerks who populated my life before. I found that most of the guys I met at OTV were top-grade individuals and are some of the very few people from whom I experience no judgment. I’m happy I have them in my life. In prison, my entire world fit into a cubby. By comparison, a small apartment in Manhattan feels like a gift. Simply walking to the Hudson River as I write this article on my phone is a luxury.

Everything in life is.

Not that being a former felon is easy. Society cares little about the former part. We retain some rights, like voting (in most states) and paying taxes, but anyone ever convicted of a serious crime will face great difficulty keeping bank accounts or credit cards, getting loans, landing jobs, and having a normal online presence. Like substance abusers risking relapse, most former felons can never shake their odious tag. Thus, their incarceration reverberates throughout their families and communities for years.

I have charmed many a person with my intellect, my irrepressible modesty, and winning personality, only to be ghosted after what I assume was a little Googling. But that’s nothing compared to the plight of underprivileged former inmates who aren’t even eligible for public housing. Where are they supposed to live? Do we have enough underpasses to house all the formerly incarcerated in this country?

People who have served long stints have difficulty fitting back into society and are further stigmatized as they struggle to adapt. “When you are stripped of your agency for so long, you often feel unable to traverse these kinds of labels that have been put on you,” the Duke scholar Brinkley-Rubinstein told me. “Your power is gone, and you have to figure out how to get that power back. Often, people do get stuck in these systems, stuck in these stigmatizing categories, in part because the dehumanization continues after people get out.”

My criminal friends and I can at least take heart, I suppose, that a former—and perhaps future—president is one of us. Many of our fellow citizens are even treating him with respect and adulation! Is this our turning point? Will we finally be accepted again as equals?

I met recently with my wealthy and connected former business partner—the one who turned me in—in the hope of settling a lawsuit between us. Yes, it wasn’t enough that I paid for our company’s sins and served time, he then sued me for the last of my assets. But during our lunch, face to face after all these years, it was clear he felt bad for doing his best to ruin my life. He even apologized. Not only that, he extended a generous peace offering.

“If Trump gets elected,” he said, “I’ll ask him to pardon you.”

He actually knows Trump, who granted clemency to some pretty unsavory characters at the end of his first term. My billionaire cousin, who had already completed his sentence, received a pardon. I’m sure now he can enjoy his new unit adjacent to his giant apartment at Trump Tower in peace. Another guy I know from OTV, Jonathan Braun, also received a pardon and immediately went back to his day job as a predatory lender. Eventually, New York state barred him from working in the industry, and a federal judge stepped in and imposed a nationwide ban on him. In a telephone interview with reporters from the New York Times, Braun said the only way he could explain his pardon was, “God made it happen for me because I’m a good person and I was treated unfairly.” Braun is considered an undeserving thug by many—you can Google videos of him threatening his borrowers and assaulting his wife and father-in-law—but in the short time we overlapped, he was nice to me. (Editor, please don’t omit the latter pandering sentence. I need all the friends I can get.)

Speaking of pardons, through my ex-wife, I happen to know President Joe Biden’s son-in-law. He’s a truly great guy, and after Biden was elected, I asked my ex whether she could float the idea with him. She adamantly refused. (We liberals do not approve of special treatment.) I was out of luck.

I am no longer rich enough to buy influence, alas, much less a pardon. All I can do is make my political voice heard through my vote. But my former business partner’s offer does raise a question I had never thought to ask:

Who should I vote for?

I never paid much attention to America’s criminal justice system until I, unexpectedly, got into serious trouble. Being labeled a criminal felt to me as unlikely as someone finding Kool-Aid on Jupiter. I was the rarest of things, an honest dealer among the myriad elegant sharks and scumbags in the very prestigious realm of high-end art sales. Or so I thought. But desperate to keep my gallery afloat, I had to juggle some money and payments. I began lying about my receivables, paying Paul while putting off Peter—until I couldn’t pay him either. This was unsustainable and, it turned out, illegal. My assistant and my business partner lawyered up, distanced themselves from me, and ratted me out. I was arrested, charged, convicted of wire fraud, and sentenced to 18 months in a minimum-security federal prison.

As another convicted felon, former President Donald Trump, has pointed out, America has a two-tiered justice system. Trump just refuses to publicly acknowledge what that really means and the fact that he’s in the top bunk, so to speak. But should he lose and end up serving time, there’s a good chance that my experience might shed light on what he would be likely to face. You see, as scary as it is to be prosecuted, my experience was a dream compared to the plight of some others I knew.

I wrote this story to dispel certain myths, but also to give you an idea of what a white-collar prosecution and incarceration is like and how much of one’s experience hinges on wealth and connections, both of which Trump has in spades. As a billionaire ex-president, the strings he could pull would be far more influential than those of a merely well-connected art dealer from New York. But whatever strings exist, they matter—a lot.

Having the cash to hire a good lawyer, and not having to rely on an overburdened public defender, is the first step toward a better outcome. As you know, it often seems as though a lawyer has a professional obligation to fight harder for a client who is paying a ton of money. But what you may not know is that the conditions of your incarceration also depend, often quite a bit, on your position in the financial and social hierarchy. And the horrific Hollywood depictions of prison life for people who are not wealthy and connected can be pretty close to the mark. Consider this snippet from a Marshall Project report on conditions at an Illinois penitentiary:

In stories that echoed with the same visceral details, dozens of men said they lived under the pressing threat of violence from cellmates as well as brutality at the hands of staff. Specifically, many men reported being shackled in cuffs so tight they left scars, or being “four-pointed” and chained by each limb to a bed for hours, far beyond what happens at other prisons and in violation of [Bureau of Prisons] policy and federal regulations.

Let’s just say that nothing like that ever happened to me. Yet just because I had it easier—easy even—doesn’t mean that incarceration isn’t life altering. Being a member of the elite (more or less) and enjoying some privilege (more or less) won’t save you from the consequences of a not-so-bad incarceration. Notably, your family, career, and social standing are generally ruined forever. Your relationships that survive may end up stronger, but many will wither and die. And if you think you will ever reach the pinnacle of whatever it was you did before you went away, well, you won’t.

I know what I’m talking about.

“Do you want good news or bad news?” my no-nonsense criminal attorney, Danny Parker, asked me one bleak morning in December 2017. The weather may have been beautiful, but all days felt bleak then. At least Danny gave me an option. His news was normally just bad.

“Bad news first,” I replied. “Always.”

“There’s a warrant out for your arrest,” he said.

I struggled to breathe. I hadn’t thought this would happen so soon, even though I’d known I was in serious trouble for about a month and a half. But the justice system works in secrecy, and as I quickly learned, you never know what’s coming.

“The good news: It’s federal.”

Until that moment, I was ignorant as to the vagaries of the criminal justice system. As it turns out, the state system is more chaotic, a bit cruder, and uneven. There are 50 disparate jurisdictions, each with its own rules, characters, and, let’s call it, charm. The Bureau of Prisons tends to be better funded than state prison systems. It also has clearer standards and is a bit more humane. And the federal system prosecutes far fewer criminals than the states do overall—about 10 percent of the total. So in a perverse way, it’s a more exclusive social group.

The prisons themselves, though still awful, are generally less so than state and private prisons. At the state level, prisoners tend to have more options for getting sentences reduced, but the federal facilities are safer and their inmates less violent. Also, the food is better.

If I were to be found guilty—and I was guilty—I would likely serve my time in a minimum-security camp. Federal security classifications range from minimum (think Trump lieutenant Peter Navarro) to supermax (El Chapo). Only about 15 percent of federal prisoners end up in minimum security. But landing in one of the nicer facilities, like Otisville or Pensacola, is exceedingly difficult. As with exclusive Ivy League schools, it usually requires hiring a consultant who can lobby public officials to improve your odds of admission.

Shocked? I sure was. I learned from my lawyers that these consultants, much like college counselors, also advise prospective, uh, freshmen on which campus would suit them best. (This applies only to nonviolent criminals. If you’re a murderer or serial rapist, all bets are off.) Once you narrow down your list of prospective prison camps, like Tom Wambsgans in Succession, your consultants pull strings to try to get you your preferred choice. And once you’re accepted, they’ll advise you on what to expect.

When it became clear I would be doing time, I called prison consultant Joel Sickler, who boasts an 80 percent success rate in landing people the facility of their choice. Given my level and type of offense (felony, wire fraud), he was confident he could get me into Otisville—which we, the cognoscenti, call OTV. Roughly half of its clientele consists of white-collar criminals: disgraced executives, unscrupulous lawyers, careless politicians, and wayward rabbis. Most of the rest are in for more serious offenses, like nonviolent drug crimes, or because good behavior at a higher-security facility earned them an upgrade. Otisville is the clubbiest of Club Feds, the Harvard of the Catskills, the yeshiva of misconduct. The best possible option for the worst part of your life.

Otisville is the clubbiest of Club Feds, the Harvard of the Catskills, the yeshiva of misconduct. The best possible option for the worst part of your life.

It likely helped that I’m Jewish because OTV is viewed as the Jewish prison. For years, advocacy groups had lobbied federal officials to develop a lockup with accommodations for religiously conservative Jews. As such, Otisville has a real Torah, a kosher kitchen, and a huge Hebrew library. It makes accommodations for the High Holidays. (I’m basically an atheist, but I would take all the help I could get.) You’d have to be a fool, Sickler told me, to cause trouble and get yourself transferred out of this promised land. “Keep your head down and don’t mess around,” he advised.

But before you book a stay, let me dispel your preconceived notions about Club Fed’s reputation for being cushy and how white-collar felons get undue perks. Much of that is exaggerated. Maybe it sounds better than that cruise you took with your in-laws, but minimum-security prison is still prison. I figured that much out pretty quickly.

Danny called me into his office one day for a horrible conversation. The US attorney was offering a deal, he informed me. If I admitted to my crimes, which are not uncommon, as I once wrote, in my profession, I could expect a lenient sentence: 51 to 63 months—4¼ to 5¼ years! He then gave me the best legal advice I’ve ever received: Take the deal without counteroffers or complaints.

This is the dirty little secret of the federal system: Once indicted, you will almost certainly lose. Plead guilty should you ever find yourself in such a mess. I know many people who tried to fight, and they all got longer sentences. Guilty or innocent, you’re fucked at that point, so you might as well accept your fate. My only consolation was that I knew I was guilty and had no desire to pretend otherwise.

After carefully researching the various bridges in downtown Manhattan—they’re all about the same height, turns out—I drew up a list of “mitigating factors” to convince the court I was still basically a good guy despite my monumental fuckup. I stressed my remorse and said I would take my punishment like a man. For this, the judge rewarded me.

Sentencing took place in 2018, on a Thursday in September, and the judge put me away for 18 months. Two weeks later, I received my assignment in the mail: I was to self-surrender at Otisville on the last day of November. (I got in! I got in!) This gave me ample time to put my affairs in order.

I couldn’t believe my luck.

To enter Otisville, you first pass through the adjacent medium-security prison. Here, the guards questioned me about every aspect of my life and then led me into a small room with shelves containing uniforms, either green or tan. “What’s your waist?” a guard asked. He then instructed me to take off my clothes and put them in a bin nearby. I had heard about this part: the strip search. I would get used to it eventually.

Front. Back. Squat. Cough. Lift your right foot. Now your left. Turn back around.

“Up,” he said, and, when I looked puzzled, he motioned to my groin. I lifted my scrotum.

“Okay,” he tossed me a green uniform. When I pointed out the pants were loose, he assured me: “You’ll get a new uniform. Don’t worry.”

After my fingerprinting and a mug shot, the officer was joined by another guard. Rosado was loud and funny and perhaps a bit scary. He locked me up in an actual cell for several hours before giving me a bedroll, taking me out to the quiet parking lot, and pointing to the top of a winding road, where I would meet my new friends.

“This is weird,” I thought as I walked, unaccompanied, up the hill.

The camp at Otisville is very different from the prison it surrounds—a spartan enclave in the mountains of upstate New York. There are only two buildings. One is a dormitory that houses 100 men in a maze of 50 cubicles with 6-foot-tall cinderblock walls. No doors. Each two-man cubicle contains a metal bunk bed, two metal cabinets, and two plastic stools. The smaller administration building has offices for the “counselor,” who oversees the camp, and the case manager, who advises and advocates for inmates. It also has classrooms, a chapel, a dorm for 20 more men, and a visiting room with all the charm of a Greyhound terminal. One of the former inmates I’d spoken with in advance captured the vibe perfectly: “It’s like going to a shitty summer camp in the ’70s—in Alabama.”

“It’s like going to a shitty summer camp in the ’70s—in Alabama.”

Walking into the dormitory for the first time, I was full of trepidation. In the movies, the new guy is always a target. But when I entered my 8-by-9-foot cube—home for the next several months—I was immediately welcomed by several mild-mannered, middle-aged guys. They gave me a toothbrush, toothpaste, deodorant, and even new shoes. I arrived with nothing, and they gave me everything I needed. It was a Friday evening. Within an hour, I found myself at a full-fledged Shabbat service and dinner, replete with prayer books, brisket, and babka. Mickey, the de facto head of Otisville’s Jewish community, gave the following speech:

“As we know, this is the Sabbath of Unity. We are all reminded that in here, we are brothers, united in our shared experience. No matter how religious anyone is or from what background, we are all Jews. The Jews of Otisville…welcome to the Sabbath of Unity.”

Where the fuck am I?

Waking up at OTV for the first time was weirdly serene. There was barely any schedule and little to do, but also little to fear. I witnessed no violence during my time there. The camp is small, and with everyone in our green uniforms, it felt like being in the Army, only without drills and commanding officers. There’s neither reveille in the morning nor a specified bedtime. You can watch TV all night, play cards, or hang out and talk. I realized I’d be having plenty of interesting conversations, as I had in the dorms back in college.

I was genuinely shocked by how accomplished, educated, intelligent, and, dare I say, normal nearly everybody was—a far cry from the cartoon villains I’d imagined. Most of the prisoners were simply average (or above-average) men who’d screwed up, misjudged, gotten too ambitious or desperate, and were turned in by someone they trusted. Just like me!

The only major drama was the occasional abrupt shakedown, during which staffers would kick us out of the buildings and rifle through our belongings, looking for drugs, booze, cellphones, and other contraband. These raids usually followed a tip that someone had brought something in, like Billy McFarland of Fyre Festival infamy, who smuggled in a phone and a recording device—stupid transgressions that led to me and some others getting strip-searched again. Spoiler alert: None of us had an iPhone up his butt.

But mostly, we just wiled away our days doing the mindless “jobs” we were assigned; working out; and playing chess, poker, Scrabble, or tennis. There was lots of free time to talk, laugh, and bond. If Trump loses the election and eventually lands at Otisville or a comparable place, I can predict how his bluster might be received. Prison, even pampered prison, is a great equalizer. The uniforms, the demeaning jobs like cleaning toilets, the standing up to be counted several times a day, the inane “programming”—one class was called “Doing Time With the Right Mind”—strip away one’s individuality and dignity. Whatever fame or fortune you had in real life means little here. As your fellow inmates will tell you, “In here, you’re no better than me.”

That sentiment was expressed to the likes of former Trump fixer Michael Cohen (in for tax evasion, making false statements, campaign finance violations), Jersey Shore’s The Situation (tax evasion), and former New York state Sen. Dean Skelos (bribery, extortion, corruption). All of them managed to check their egos at the gate. Could Trump? A prisoner who acts as though he deserves special treatment tests the patience of his peers. And running afoul of their expectations can make for an isolating experience.

Thriving at a place like Otisville also requires a very non-Trumpian trait: selflessness. Inmates, despite their meager possessions, are usually quick to share their coffee hoard or shaving cream with peers who have run out. Commissary comes but once a week, and strict spending limits guarantee that everyone will be short of something at some point. There are also small indulgences from the outside that get shared on the inside—books and magazines are traded frequently; Cohen would give me his “cryptic” crossword from the Financial Times. Then there’s the shared intellectual property, knowledge, and expertise, and the legal, financial, or personal advice, whether good or not. Nobody expects anything in return. In fact, the long stretches of idleness and the need to coexist peacefully means that most of the guys look forward to helping a fellow inmate. Could Trump manage that?

He’d have to learn.

An age-old question about penal systems is whether they are designed to rehabilitate or simply to punish. America focuses on the latter. Formal punishment at Otisville ranges from relatively benign (cleaning the latrines) to harsh (a stint in the “Special Housing Unit,” or SHU, a.k.a. solitary confinement). But a big part of the punishment at any prison, even OTV, is the crushing boredom. Every inmate faces an immediate and severe demotion of self-worth and confidence. By the time you enter, you’ve lost everything you most value. Minimum-security prison may be a respite from the ferocity of prosecution, but once you’re in, boredom becomes your enemy.

The most insidious epidemic in prison—though I got out before Covid hit—is mental illness. Most of the inmates I knew seemed to experience almost constant depression and despair. In many cases, their pre-prosecution lives were filled with substance abuse, anxiety, paranoia, OCD, ADHD, and other mental issues that contributed to their extreme behavior. I don’t know, for instance, what might cause a successful financial adviser to gamble away tens of millions of dollars of his clients’ money, but it can’t be psychologically healthy. According to the New York State Bar Association, an estimated 70 percent of incarcerated people show symptoms of mental illness, and up to 1 in 3 have serious diagnoses such as bipolar disorder or schizophrenia. The comparable figure for the free world is about 1 in 10.

I reached out to Lauren Brinkley-Rubinstein, an associate professor of population health sciences at Duke University who focuses on incarceration, to ask about this. Given our insufficient public investment, “who ends up treating mental health? Well, jails and then prisons, primarily,” she told me. “Because there are no community alternatives. It’s a sort of perfect storm of people who are under-resourced and then traumatizing them further.”

“Who ends up treating mental health? Well, jails and then prisons, primarily. Because there are no community alternatives. It’s a sort of perfect storm of people who are under-resourced and then traumatizing them further.”

Even OTV’s most noteworthy inmates—formerly hotshot lawyers, esteemed doctors, and titans of industry—struggled with their alienation from society. If you thought Club Fed would offer adequate psychological support, think again. There were no therapists on hand beyond the one who managed care for the broader facility, including the medium-security prison, and she was rarely at the camp. Even accessing our prescriptions was a challenge. I had to lobby hard for my Wellbutrin after the medical team initially refused to give me my prescribed dose. When the doctor asked what I thought would happen if I switched meds, I replied, “suicide,” which apparently was enough of a magic word to change their stance.

One antidote to the boredom, however, was the revolving door of new enrollees. Before Trump pardoned him, his disgraced former campaign manager Paul Manafort did some time in a Otisville-esque facility in Pennsylvania. Trump adviser Steve Bannon, ineligible for minimum-security status on account of a superseding state fraud indictment, was just released from Danbury, a decidedly harsher low-security federal institution in Connecticut. Trump’s loyal accountant Allen Weisselberg was in the unenviable position of doing state time at Rikers Island, but with two sentences that didn’t even add up to a year, he survived. Trump himself could wind up in Otisville one day if convicted of federal crimes, but I hope not.

We have our standards.

I hereby interrupt this story to offer a quick cheat sheet of my own selected wisdom for indicted Trump officials and others who end up serving time—even at Club Fed:

• Time flies: Your days will seem to drag on forever, but the months and years move fast. And both for the same reason: Nothing much happens in prison. After a while, time becomes irrelevant. One new year blends into the next, and though you don’t feel it, you can sense the time zooming by and leaving you and your fellow inmates behind.
• Everyone hates a rat. Yes, just like on TV.
• Don’t expect any privacy: With more than 100 guys under one roof, there’s a good chance someone is watching you all the time.
• Remorse either: The idea that contrition will miraculously appear for those who sit and think deeply about the crimes they committed is just not a thing. When prisoners ponder their actions, it is usually to justify them. Admitting one’s faults is not only difficult but unnatural. People can’t walk around all day believing they are assholes. Denial, minimization, pride, and forgetfulness are essential to moving on. The rare person, like me, who is remorseful in prison probably came in that way.
• Enablers are everywhere: “It’s not like you killed anyone,” is a reassuring sentiment I heard a million times at Otisville. But I brushed it off. Because it was guilt and remorse that liberated me from the bitter feeling that I got screwed by the system. Blaming myself actually made me feel better.
• America needs to make its prisons less hellish. The relatively humane conditions at OTV should be much closer to the norm. We were all appalled when Vladimir Putin treated Russian opposition leader Alexei Navalny so harshly in prison. Are we so far behind? People who commit crimes are still human, and they need a modicum of dignity. Some of them offered no mercy to their victims, so they don’t deserve any, the logic goes. But do we really want to be as bad as the bad guys at their worst?

Now back to the story.

Perhaps the most surprising thing I learned at OTV was that prison can catalyze a positive change in a person’s life. After a period of adjustment, including plenty of self-flagellation and disbelief at my stupidity, something began to shift. Nothing spiritual, but rather, I felt unexpectedly motivated by the trauma of confinement. I began writing, dreaming, making friends, and having deep conversations. I read all the books I’d previously only pretended to have read, got myself fit, and laughed my ass off. I later found out I was experiencing a phenomenon called post-traumatic growth (PTG) that was identified in the 1990s by psychologists Richard Tedeschi and Lawrence Calhoun and which psychologists and behavioral scientists have analyzed in depth.

PTG is experienced by a small percentage of people who endure something awful and unforeseen. Just as an actor might repurpose stage fright into the energy needed to perform, a person with PTG uses trauma to become a better and more productive person.

Lucky, right?

You bet. Now that I’m out, I am as happy as I was as a child. I’m less interested in money or success and more interested in just reducing stress and being with my girlfriend, kids, and friends—the real ones, not the jerks who populated my life before. I found that most of the guys I met at OTV were top-grade individuals and are some of the very few people from whom I experience no judgment. I’m happy I have them in my life. In prison, my entire world fit into a cubby. By comparison, a small apartment in Manhattan feels like a gift. Simply walking to the Hudson River as I write this article on my phone is a luxury.

Everything in life is.

Not that being a former felon is easy. Society cares little about the former part. We retain some rights, like voting (in most states) and paying taxes, but anyone ever convicted of a serious crime will face great difficulty keeping bank accounts or credit cards, getting loans, landing jobs, and having a normal online presence. Like substance abusers risking relapse, most former felons can never shake their odious tag. Thus, their incarceration reverberates throughout their families and communities for years.

I have charmed many a person with my intellect, my irrepressible modesty, and winning personality, only to be ghosted after what I assume was a little Googling. But that’s nothing compared to the plight of underprivileged former inmates who aren’t even eligible for public housing. Where are they supposed to live? Do we have enough underpasses to house all the formerly incarcerated in this country?

People who have served long stints have difficulty fitting back into society and are further stigmatized as they struggle to adapt. “When you are stripped of your agency for so long, you often feel unable to traverse these kinds of labels that have been put on you,” the Duke scholar Brinkley-Rubinstein told me. “Your power is gone, and you have to figure out how to get that power back. Often, people do get stuck in these systems, stuck in these stigmatizing categories, in part because the dehumanization continues after people get out.”

My criminal friends and I can at least take heart, I suppose, that a former—and perhaps future—president is one of us. Many of our fellow citizens are even treating him with respect and adulation! Is this our turning point? Will we finally be accepted again as equals?

I met recently with my wealthy and connected former business partner—the one who turned me in—in the hope of settling a lawsuit between us. Yes, it wasn’t enough that I paid for our company’s sins and served time, he then sued me for the last of my assets. But during our lunch, face to face after all these years, it was clear he felt bad for doing his best to ruin my life. He even apologized. Not only that, he extended a generous peace offering.

“If Trump gets elected,” he said, “I’ll ask him to pardon you.”

He actually knows Trump, who granted clemency to some pretty unsavory characters at the end of his first term. My billionaire cousin, who had already completed his sentence, received a pardon. I’m sure now he can enjoy his new unit adjacent to his giant apartment at Trump Tower in peace. Another guy I know from OTV, Jonathan Braun, also received a pardon and immediately went back to his day job as a predatory lender. Eventually, New York state barred him from working in the industry, and a federal judge stepped in and imposed a nationwide ban on him. In a telephone interview with reporters from the New York Times, Braun said the only way he could explain his pardon was, “God made it happen for me because I’m a good person and I was treated unfairly.” Braun is considered an undeserving thug by many—you can Google videos of him threatening his borrowers and assaulting his wife and father-in-law—but in the short time we overlapped, he was nice to me. (Editor, please don’t omit the latter pandering sentence. I need all the friends I can get.)

Speaking of pardons, through my ex-wife, I happen to know President Joe Biden’s son-in-law. He’s a truly great guy, and after Biden was elected, I asked my ex whether she could float the idea with him. She adamantly refused. (We liberals do not approve of special treatment.) I was out of luck.

I am no longer rich enough to buy influence, alas, much less a pardon. All I can do is make my political voice heard through my vote. But my former business partner’s offer does raise a question I had never thought to ask:

Who should I vote for?