Diehard Trump Lackey Is in for a Strange Trip Behind Bars

·5 min read
Photo Illustration by Luis G. Rendon/The Daily Beast/Getty/Reuters
Photo Illustration by Luis G. Rendon/The Daily Beast/Getty/Reuters

Disgraced former Trump Organization chief financial officer Allen Weisselberg recently found himself in a tough spot I know all too well. Like Weisselberg, I was prosecuted for tax fraud by the government. And like him, I was “dead to rights” and looking for a way to mitigate my circumstances. If you really want to know how all this works, how the government handles offenders like us, and what he’s going through, I’m your guy.

It’s not fun.

Weisselberg refused to testify against Donald Trump directly, frustrating what remains of the criminal investigation into the former president by Manhattan prosecutors. But he has agreed to testify against his former employer—that is, Trump’s company.

Often, the government stretches the torture of what comes next for a ridiculous period of time. In my case, it was five-and-a-half years between the time I was presented with a search warrant and the day I surrendered to lock-up. By the time I turned myself in, it felt like a denouement. I could finally see light at the end of the tunnel. My year behind bars was a walk in the park. The five-and-a-half leading up were horrible.

Weisselberg got lucky that way. His torture has only lasted a little over a year, though there may be a few more months left before he actually goes inside. Multiple outlets have reported that Weisselberg will likely serve five months at New York City’s notorious—and increasingly deadly—Rikers Island jail. But that’s not assured. One presiding judge declares how long his sentence will actually be. Often in these cases, the prosecutors will write what’s called a 5k letter to that judge, describing a defendant’s cooperation in a case— and that perhaps he should go easy on the old boy.

I did get that letter myself, owing to my detailed description of exactly how the sex work business I took part in functioned—and my willingness to be an expert witness in other cases. But because I wouldn’t sandbag my customers in the manner the government wanted, it was a tepid recommendation at best.

<div class="inline-image__credit">Photo by Curtis Means/AFP via Getty Images</div>
Photo by Curtis Means/AFP via Getty Images

In Weisselberg’s case, he has refused to directly implicate his former boss, though you can bet he’ll have to take the stand if and when the Trump Organization itself goes to trial.

As for his potential vacation at Rikers, Weisselberg has two choices: The first is protective custody, a special unit whose prisoners are insulated from the general population because of their notoriety as snitches or their more general fame or infamy. Movement is restricted and often takes place alongside escorts, so they don’t get jumped.

When I arrived at Rikers for my November 2019 stay (after serving 311 days at MCC federal prison), I conferred with a couple of guards about whether I should request protective custody. Their attitude was, “No, do not request protective custody. The food sucks and you’ll hate it. PC is for snitches and pussies. You’ll be fine.” Bear in mind, that’s a guard’s take on the option. I chose to remain in the general population.

But thanks in part to his high profile and political background, Weisselberg will almost certainly go the confinement (PC) route. He’ll hole up for his time, and grin and bear it. If he for some reason landed in general population, the administration would probably send him to the unit where I stayed: an air-conditioned dorm filled with a significant number of older inmates (like I was) mixed in with noisy gangbangers who will accept you if you answer some key questions right (like “Are you a chomo?”—or child molester). Fluency in Spanish is also a big help. And there I thought high school was a waste of time!

Trump’s Money Man Allen Weisselberg Pleads Guilty

The food at Rikers isn’t the best. In fact, it was the worst of the three institutions where I did my time. And the commissary isn’t a lot better. The jail is also going through one of the deadliest stretches in its history, though it’s safe to say the Department of Correction would likely take pains not to allow Weisselberg to be subject to wanton violence.

I see a lot of trail mix in Weisselberg’s future. But if he’s resolute—and his lawyers are adept at orienting him to what’s coming—he’ll survive. The company in protective custody will consist mostly of so-called snitches, inmates who might be targeted for some identity-based reason, and even an infamous white-collar criminal or two. But if he’s lucky, Weisselberg will find somebody with whom he can relate on some level to make it through emotionally and spiritually.

And even if Weisselberg finds no kindred spirits in his unit, he can occupy his time reading. Family and friends are allowed to forward magazines and soft-cover books via mail. Weisselberg may also sign on for manual labor if he so desires—but only within the confines of his unit. As an inmate in protective custody, he will almost certainly not be able to seek prison employment outside of that area.

Then again, even if he’s no longer getting rent-free apartments or cars, it’s hard to imagine he will need the cash.

Read more at The Daily Beast.

Get the Daily Beast's biggest scoops and scandals delivered right to your inbox. Sign up now.

Stay informed and gain unlimited access to the Daily Beast's unmatched reporting. Subscribe now.