What Jail Would Be Like for Trump

donald trump

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Where would he do his time?

A version of this article originally appeared on Jonathan Alter’s substack Old Goats, which you can subscribe to here.


Day 12 of Trump’s hush money trial began with high drama when Judge Merchan warned Trump that his 10th violation of the gag order would be his last or he’d be sanctioned with jail time.

Merchan told Trump that he was well aware that “you are the former president of the United States and possibly the next president as well” and that he understood that jailing Trump “would be disruptive to the proceedings.” The judge said he also worried about the court officers, corrections officers, Secret Service, and other law enforcement personnel who would be involved in Trump’s incarceration.

“The magnitude of that decision is not lost on me,” Merchan said. “But at the end of the day, I have a job to do.” Trump’s offenses, he noted calmly, represented “a direct attack on the rule of law, and I cannot allow that to continue.”

In March, I posted a column here that argued that the most appropriate punishment for the sociopath on the loose would be to make him pick up trash…but by the end of the day, I was back to favoring incarceration.

My new courtroom friend, George Grasso, a former cop and retired city judge who attends court as a spectator, told me that the security requirements of having a former president outdoors for hours on end would be a nightmare for the Secret Service. It occurred to me that Trump, in an orange jumpsuit, would make him an easy target from a high building. It wouldn’t be so horrible if Trump accidentally choked on a pretzel, as George W. Bush once did, but someone harming him physically would be a bad thing for the country. 

Society’s task is to bring Trump to justice and make sure he is not re-elected president, and if he can be disgraced and humiliated in the process, all the better. But we shouldn’t encourage or even hope for violence. That’s Trump, not us.

What we must do instead, as the judge noted, is stand up for the rule of law. In this case, that means jailing him if he opens his yap one more time to attack witnesses or the jury.

Where would he do his time? Until recently, it might have been at the huge jail next door, “The Tombs,” an infamous dungeon that made Rikers Island look like Mar-a-Lago. Unfortunately, the Tombs was razed last month, so the most likely place for Trump to spend a night or two is a holding cell on the 16th Floor of the Manhattan Criminal Courthouse, one floor up from the courtroom. 

View Of Prisoner Cell at Rikers Island from 1974
The New York City Tombs in 1974. Photo shows empty cells inside Cell Block 7. (Getty)

While Trump would enjoy a “solitary” instead of sharing a larger cell with other inmates, the accommodations are satisfyingly unpleasant. The bed, if you could call it that, is narrow and hard, with the harshest blanket Trump has ever slept under and a sheet thread count one-tenth of his usual 500. Instead of a gold-plated commode like the ones that Trump enjoys at his many homes, the former commander-in-chief would find a low metal toilet, quite possibly missing a seat. 

Thanks to the watchful presence of his Secret Service detail, Trump would likely be allowed to skip the standard practice of turning over his belt and shoelaces to avoid a suicide attempt, a procedure that did not help his friend and fellow man-on-the-make, Jeffrey Epstein. In this regard, Trump would be more fortunate than we reporters, who must take off our belts and watches to get through two metal detectors every time we enter the building. The first week of the trial, I decided to go belt-less, which makes my low-slung pants resemble those of the hand-cuffed defendants I’ve seen marched through the halls.

While it’s unlikely we would catch a glimpse of Trump in an orange jumpsuit, there’s always hope. In 1928, an enterprising photographer lied his way into the execution chamber with a camera tied to his toe and got a famous shot of Ruth Snyder in the Electric Chair. 

For Trump, the most onerous part of his incarceration might be the disruption of his morning ritual. Trump said last month that it would be his “great honor” to be jailed by the judge, whom he routinely calls “crooked.” But some things are more important than honor—like hair. Absent his hairdresser and product, how would he show up in court the next day without the dreaded “bed head” for all the world to see?

Given that, I expect Trump will zip it for the next couple of weeks, though his lack of impulse control might kick in when Michael Cohen takes the stand.


Jonathan Alter is an award-winning author, political analyst, documentary filmmaker, columnist, television producer, and radio host. He’s authored three New York Times bestsellers: The Center Holds: Obama and His Enemies (2013), The Promise: President Obama, Year One (2010), and The Defining Moment: FDR’s Hundred Days and the Triumph of Hope (2006). His most recent book is His Very Best: Jimmy Carter, a Life (2020). Alter has written for the New York Times, the Washington Post, the Washington Monthly, the New Yorker, Bloomberg, the Daily Beast, and other publications.