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What Inmates Are Saying About Trump Possibly Going to Prison

"There would have to be some kind of protective custody situation."
(Photo by Win McNamee/Getty Images)

The events of this past year made it easier than ever to envision Donald Trump being charged with a crime. The sentencing memos recently issued by Special Counsel Robert Mueller in the case of the president's convicted former fixer, Michael Cohen, argued the then-candidate—a.k.a. "Individual 1"—was a party to financial felonies. Specifically, Trump was said to have overseen the silencing of two women who claimed they had affairs with him, and whose stories might have damaged his bid for office. While Mueller did not argue Trump had "knowingly and willfully violated the law," as would be required for his prosecution, Democrat Adam Schiff, the incoming chair of the House Intelligence Committee who will soon have new investigative powers over the White House, went so far as to say the president "faces the real prospect of jail time" in that case. He's not the only former prosecutor in Congress going there. The Russia investigation is still swirling—and Trump's claims that he had no business dealings with Moscow late into his candidacy keep getting debunked—but the Cohen case, which is separate, remains the probe that likely presents the clearest danger to his status as a free man.


As a two-plus decade denizen of the federal prison system, these latest legal developments—coming after years of steady revelations about the president thumbing his nose at the rule of law—made me curious whether inmates were tracking Trump's exposure to prosecution. Did people who had been caught up in (and convicted by) the American criminal-justice system actually expect the heir to a real-estate fortune whose family cheated on their taxes and who somehow became the most powerful man in the world anyway to get his? Was the prospect of a former president joining them—DOJ guidelines hold that a sitting president cannot be indicted, even if some legal scholars disagree—in one of the country's correctional institutions actually a thing people on the yard were entertaining? Were inmates even looking that far ahead?

Conversations with federal inmates at men's prisons pointed, first, to Trump's legal drama producing plenty of chatter inside the "belly of the beast," as we tend to call it. But a general consensus emerged that the "Teflon Don," as some called him, would never see the inside of a cell. Maybe Donald Trump, Jr., or Jared Kushner might eventually be prosecuted for some crime or another related to, say, perjury or lying to the FBI, inmates suggested. But the idea that Donald Trump himself would go down was difficult for most inmates to imagine.

Not that it wasn't a tantalizing possibility.


An inmate who called himself "Po Boy," a native of Chicago doing time on a parole violation who like several others in this article requested his real name be withheld for fear of retribution, argued Trump carries himself like a mob boss. In that sense, the inmate suggested, Trump was probably safe, even if he shouldn't be.

“He went out and got himself a real mob lawyer in [Rudy] Giuliani," Po' Boy told VICE. "If he don't go to jail for all the crimes, and I mean all the crimes he's committed, then no one should ever say we have equal justice in this country. Let's keep it real: Trump’s worse than any dope dealer or white-collar criminal in here. He makes Bernie Madoff look like a saint. As a black man who was proud to have Obama as president and sick to see how Fox News treated him, I now watch how Fox treats Trump—a real criminal—and it makes me sick.”

Another inmate who called himself "Show Boat," an ex-cop doing time for robbery, said he thought Trump had been damaged goods since well before he entered the political arena, with a long laundry list of crimes and criminal characters attached to his name.

“We have a president whose entire life has been a con, and he was so good at it that he conned his way into the White House, aided by a poor Democratic presidential candidate and foreign governments," Show Boat told VICE, adding, candidly, "I want to see Trump go to prison.”

He's not the only one.


“Even though we do have a two-tier justice system, I think it would send a powerful message to go ahead and make Trump pay for what he's done," an inmate who called himself "Red" and was doing life for a meth conspiracy told VICE. "Fox News contributor Andrew McCarthy, who also happens to be a former prosecutor, is saying that Trump is likely to be indicted on at least campaign finance laws. There’s no doubt in my mind that the real powers that be will take down Trump.”

But the prevailing sentiment was that despite how bad it may look for Trump, he'll never be locked up. That's just now how the rule of law works in this country.

“The odds of our current president ever going to prison are slim to none," Robert Lustyik, a former FBI agent serving 15 years for corruption, told VICE in an email. “People don't realize that he’s protected from any indictment while sitting in office. He can only be charged after leaving the Oval Office, thus insuring the integrity of the institution of the presidency worldwide. If he’s re-elected, that window probably closes. Therefore both sides can argue, make allegations, point fingers and gossip all they want. The simple truth is that a second term almost guarantees Trump stays a free man.”

As for how things might go in the event that Trump actually did get convicted and sentenced to hard time, in 2021 or otherwise, inmates found it hard to imagine him, you know, fitting in.


"There would have to be some kind of protective custody situation, even in low-security prisons," Jeremy Fontanez, who was serving a life sentence for murder and other crimes in West Virginia, said in an email. Alluding to the unprecedented prospect of Secret Service agents trailing a former president in a federal prison compound, Fontanez conceded it was an absurd notion.

But this is Trump we're talking about. "I wouldn't put it past them," he told me.

Robert Rosso contributed reporting to this story.

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