Ezra Chowaiki and fellow inmates at the Otisville Federal Corrections Center.Courtesy Ezra Chowaiki

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........

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