Will Trump Be Safe in Jail?

Photo Illustration by Luis G. Rendon/The Daily Beast/Getty Images
Photo Illustration by Luis G. Rendon/The Daily Beast/Getty Images
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If Donald Trump is actually jailed for what appears to be a near-pathological inability to abide by a gag order handed down by the New York State Supreme Court judge overseeing his criminal hush-money trial, the logistics of such an undertaking will present a first-of-its-kind quandary for authorities.

On Monday, Judge Juan Merchan fined Trump $1,000 for violating the gag order yet again, cautioning the former president that he was playing with fire.

“I’ll find you in criminal contempt for the tenth time,” Merchan warned from the bench. “It appears that the $1,000 fines are not serving as a deterrent. Therefore, going forward, this court will have to consider a jail sanction.”

Contempt of court carries a $1,000 per violation and/or up to 30 days in jail.


Former Trump Organization CFO Allen Weisselberg, now serving a five-month bid for perjuring himself in the former president’s civil fraud trial, is doing his time at Rikers Island’s West Facility, according to jail records. And although experts say the chances of Trump in fact seeing the inside of a cell remain extremely slim, the lockup would be one possible destination for the twice-impeached ex-commander-in-chief, a corrections insider speculated to The Daily Beast.

The West Facility, one of seven active facilities on the 413-acre island in the East River, is home to the New York City Department of Correction’s Communicable Disease Unit (CDU) but has separate cells for high-profile inmates and those in protective custody.

Other notable guests of the West Facility have included ex-International Monetary Fund head Dominique Strauss-Kahn (rape, later acquitted); former NFL star Plaxico Burress (weapons possession, later sentenced to two years); and disgraced movie mogul Harvey Weinstein (rape, presently serving a multiyear sentence on convictions in two states—one of which was recently overturned on appeal.)

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Some have theorized about potentially housing Trump in an unused jail on Rikers, such as the shuttered Anna M. Kross Center. There is also a decommissioned jail barge anchored just off Rikers, as well as a federal detention center close to Manhattan Criminal Court, where Trump is being tried, which was shut down after convicted pedophile and onetime Trump associate Jeffrey Epstein died by suicide in 2019.

What is clear, however, is that incarcerating Trump would be an incredibly dicey proposition. For starters, as Secret Service spokesman Anthony Guglielmi told The Daily Beast, Trump is entitled to round-the-clock protection even if he’s in jail. And having a coterie of armed bodyguards inside a city jail, according to former New York City Department of Correction (DOC) Commissioner Martin Horn, runs completely counter to the no-firearms policy that is standard in New York and across the nation. (Guns are carried by officers, for example, while transporting inmates, by those patrolling outside the walls, and by members of special units that respond to emergencies inside.)

Furthermore, Horn told The Daily Beast, housing Trump by himself in an otherwise empty facility could constitute solitary confinement, which is outlawed in New York.


If he were to be treated like any other detainee, Trump’s stay on Rikers would begin with the standard intake process, which includes a strip search and a medical screening. Those charged with misdemeanors are given a “less invasive” search, according to The City. In 2022, Rikers inmates managed to seize control of the intake unit after stealing riot gear from a DOC captain’s office. Everyday inmates have described their arrival at Rikers as a special form of hell, standing by while watching others in the throes of withdrawal, fighting over space on bullpen benches and floors, and fielding bologna sandwiches tossed at them by officers.

Trump would likely avoid this, of course.

Processing normally takes as long as 16 hours, but has been known to last weeks, according to a 2022 report issued by a federal monitor appointed to oversee conditions at Rikers, which it described as “horrifying.”

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“The Monitoring Team’s February 2022 site visit found the conditions at one intake to be particularly distressing—a toilet was overflowing with feces and an individual was sleeping on the floor outside one of the intake pens,” the report said. “If staff were aware of these problems prior to the Monitoring Team’s visit, they did nothing to correct the situations. In addition to poorly supervised spaces and unsanitary conditions in these units, the risk of violence to individuals in intake is also a continuing cause for concern.”

As one former Rikers detainee wrote in 2020 for The Daily Beast, onboarding at Rikers is “not fun.”


Trump’s reported appetite for greasy fast food would not be sated at Rikers, according to Paulette Johnson, who oversees nutritional services on the island. Still, meals on Rikers are healthful and well-balanced, she said. In the 2016 book Food and the City, Johnson told author Ina Yalof that the various industrial-size kitchens on Rikers use only three types of cooking equipment: 100-gallon vats, combi ovens (convection and steam), and rotisseries. The rotisseries, Johnson said, can turn out 400 roast chickens in 15 minutes. The combis, she told Yalof, can handle 2,000 meals at a time. Knives are kept in locked boxes, and civilian staff must sign them out for use.

“A lot of people, when they think of prison food, they think of slop,” Johnson said. “They think of putting everything in a pot, stirring it around, and dumping it on a tray. They think of inferior food being prepared and served in an inferior manner. This is the total opposite of what’s happening here.”

According to Johnson, the menus at Rikers are all “heart-healthy,” which she described as her “dream come true.” Trans fats were phased out years ago, and black pepper, paprika, and garlic have largely replaced salt in Rikers recipes.

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“The prisoners don’t get anything fried,” Johnson said. “Nothing. And it’s whole grains only, as well. We started this process 20 years ago when the DOC undertook a kitchen renovation project. First thing we did was get rid of the fryers. No fryers? No fried foods! Easy enough… Over the course of the day, the Rikers Island inmates probably eat much healthier than most people.”

For a “normal” Rikers inmate, a continental-style breakfast is served at 5 a.m., which consists of hot or cold cereal, fresh fruit, and coffee or tea. Lunch is at 11 a.m., and includes a protein, a starch, a vegetable, fresh fruit, and a salad. Dinner is served at 4 p.m., and the menu is along the same lines as lunch, Johnson said. Baked chicken, turkey stew, and chili con carne are typical menu items, according to one former Rikers cook. (Federal prison menus look virtually the same.)


If Trump receives any visitors while at Rikers, they will not be allowed to bring gifts, which must be mailed to the detainee. Packages cannot weigh more than 15 pounds and must be less than 24 inches wide, 12 inches high, and 14 inches deep, according to DOC regulations. Detainees are allowed “one cubic foot (12 inches X 12 inches X 12 inches) of non-legal printed materials, including soft and hardcover books, magazines, newspapers, periodicals, pamphlets, advertisements and other printed articles, in any combination.”

“Toiletries and food items are prohibited,” the DOC regulations state. “They must be purchased by the inmate in the commissary. Cash for inmate fund accounts is no longer being accepted by mail. Only money orders and cashier checks will be accepted by mail. NO clothing, footwear or accessory is permitted in the colors of red, yellow, and light blue. Permissible colors for clothing and accessories for detained persons are: Brown, Grey or White, but no button down white shirts. Permissible colors for footwear are: Black, White or Grey or any combination of the three.”

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Detainees “are not permitted to wear personal footwear, except for scheduled on-trial court appearances or significant family events,” the rules continue. “Upon admission, all detainees are issued one pair of Department issued footwear. All detainees are allowed to have one (1) pair of personal footwear in their property, which will only be re-issued for scheduled on-trial court appearances or significant family events.” Upon release, Rikers inmates can pick up their valuables—money, keys, wallet—at the Samuel L. Perry Center, located on the island and accessible via the Q100 bus.

“It’s very disorienting for people,” Barbara Hamilton, head of the Legal Aid Society’s Incarcerated Client Services Unit, told The City earlier this year. “Nothing is in your control anymore. Showering. Using the facilities. Eating.”

Cash is considered contraband at Rikers, and money must be put on an inmate’s “books” if they want to purchase items at the commissary. According to the federal monitor’s report, “delayed access to commissary” is one of the triggers causing “tension that ultimately leads to uses of force and violence on the housing units.”

But with Trump likely cordoned off from everyone else, he wouldn’t have to worry about such indignities.


Broadly speaking, Horn, the former DOC commissioner, now a professor at Manhattan’s John Jay College of Criminal Justice, would be highly surprised if Trump spent any time at all on Rikers Island over the gag order.

As he told The Daily Beast, “Any defendant, 77 years old, with no prior criminal convictions—a non-violent crime, not addicted to drugs, not likely to commit another crime—it would not be appropriate to send him to jail, even though the statute permits it. It’s not mandatory, and it’s highly unlikely. The statute allows for other sentences: probation, conditional discharge, a fine.

“I think jail is highly unlikely.”

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