In the past several months, Donald Trump has had a burning question for some of his confidants and attorneys:
Would the authorities make him wear “one of those jumpsuits” in prison?
As the criminal cases against him have piled up, the former president and 2024 GOP frontrunner has wondered aloud in recent months about what life would be like if he’s convicted, and if appeals fail. While Trump publicly professes confidence, privately, three sources familiar with his comments say, he’s been asking lawyers and other people close to him what a prison sentence would look like for a former American president.
Would he be sent to a “club fed” style prison — a place that’s relatively comfortable, as far these things go — or a “bad” prison? Would he serve out a sentence in a plush home confinement? Would government officials try to strip him of his lifetime Secret Service protections? What would they make him wear, if his enemies actually did ever get him in a cell — an unprecedented set of consequences for a former leader of the free world.
What would happen — including in the Fulton County, Georgia criminal case against him and various co-defendants — if he were convicted and sentenced, but also re-elected?
The private questions are a departure from the air of supreme confidence invincibility Trump has projected. In interviews and elsewhere, he has claimed that the thought of losing in court and going to prison simply cannot enter his mind.
“I don’t even think about it,” Trump told NBC’s Kristen Welker during an interview last week. “I’m built a little differently I guess.”
Trump’s attorneys like Alina Habba have amplified that bravado. Habba told Fox News’ Shannon Bream last month that the former president was so confident he would be vindicated that he’s not even preparing for his various trials. “If it was a normal person, honestly Shannon, I could understand the concern,” she said, adding that “You don’t have to prep much when you’ve done nothing wrong.”
But now out of office, sources close to Trump and those who’ve heard him ask these questions about a hypothetical sentencing tell Rolling Stone that it’s clear the gravity of his mounting legal peril is getting to Trump, regardless of whether the former president can admit to it in public.
A Trump spokesperson did not respond to questions from Rolling Stone.
Trump’s private concerns mark a significant departure from some of the private confidence he displayed during his first brush with a special counsel investigation. One former White House official who worked on the Mueller investigation said Trump was not remotely worried about consequences from the Russia inquiry. Not only was he convinced he had done nothing wrong; Trump was also aware of the Justice Department policy that a sitting president cannot be indicted while in office.
Even before he faced criminal charges, Trump showed at least a distant concern about looming criminal liability. As Rolling Stone reported in 2022, the former president told associates that he was looking forward to running for president again at least in part because the office would afford him at least temporary immunity from prosecution. He and his legal team have also grasped at exotic legal theories in seemingly desperate attempts to shut down the cases against him in Fulton County and New York City.
Experts say that, in the event of a conviction, Trump would still be entitled to Secret Service protection for the rest of his life. But the answers to many of his other questions — like where he’d have to serve a sentence and under what conditions — would vary based on whether he’s convicted and on which charges.
Still, the former president faces daunting math given the scope of charges against him. At the moment, Trump is set to stand trial in four criminal cases spanning 91 charges, including several felony counts.
The jeopardy places the former president in rare company with few historical examples to illustrate what he might expect in the event of a conviction. The closest equivalent to Trump’s legal predicament lies in the 1973 federal prosecution of Nixon Vice President Spiro Agnew on charges related to bribes from his tenure as governor of Maryland. In that case, Agnew struck a plea deal that netted him only probation.
Like Trump, Agnew campaigned as a populist pugilist eager for conflict with the political left. But as the criminal investigation of him mounted, privately “Agnew was utterly terrified of going to jail,” his biographer Charles J. Holden told Rolling Stone. “He was still terrified of that and the humiliation of it haunted him as well.”
