Can Trump run for president from prison? Yes, and it’s been done before.

Those requirements are minimal: A person must be at least 35 years old, must be a natural-born citizen and must have lived in the U.S. for at least 14 years.

The Supreme Court has never weighed in directly on those requirements, Mazo said, but in a 1995 case, the justices rejected an attempt by Arkansas to impose term limits on its U.S. senators and House members. That logic seems to extend to any attempt by a state to declare a presidential candidate ineligible for reasons not spelled out in the Constitution, the professor added.

States remain free to exclude felons from the ballot for state and local positions, just not federal ones, Mazo said. “In the states, we have different rules,” he said.

What would happen if a person in prison actually won the presidency is a thornier question. Would the new president have to govern from a jail cell?

Probably not. Many legal experts argue that a state-court sentence would have to be held in abeyance. Whether a federal sentence would also have to be postponed is less clear, but the question might not matter if the new president used his pardon power to set himself free — or preemptively pardon himself from any pending federal charges. (The pardon power covers federal crimes, but not state crimes like the New York charges for which Trump was indicted this week.)

Stebenne noted that Trump has extra motivation to win and dodge whatever charges federal prosecutors may be considering against him. “It provides a strange reason to run, but a powerful incentive,” the professor said. “If Trump attempted to do that, it would probably create some sort of constitutional crisis.”

An exotic cast of characters

After Debs, the history of prisoners seeking the presidency is peppered with eccentric personalities.

Conspiracy theorist Lyndon LaRouche ran for the White House eight times, with one of those bids — in 1992 — coming as he served a 15-year sentence for mail fraud, conspiracy and tax evasion. He was released in 1994 and died in 2019.

And there’s already one prominent declared candidate running from prison in the 2024 contest: Joseph Maldonado-Passage, better known as Joe Exotic. The former zookeeper and star of the Netflix “Tiger King” series is running as a Libertarian after filing candidacy papers in February with the Federal Election Commission.

Maldonado-Passage is mounting his presidential bid from a medical center for federal inmates in Fort Worth, Texas, where he’s serving a 21-year sentence for a slew of animal trafficking and abuse offenses as well as attempting to arrange the murder-for-hire of a rival private zoo owner, Carole Baskin.

Despite the fact that it came over a century ago, Debs’ candidacy may bear the closest resemblance to the one Trump could wind up pursuing if he’s jailed before November 2024.

One notable parallel is that Debs was imprisoned under one of the same statutes that Trump is now being investigated for potentially violating: the Espionage Act. Debs was accused of violating provisions of the law that prohibited encouraging insubordination in the armed forces or interference with the enlistment of troops.

More than a century later, federal prosecutors have indicated in court filings that they’re investigating the presence of classified documents at Trump’s Mar-a-Lago estate in Florida as a potential violation of another Espionage Act provision barring “willful retention” of national defense information after a request to return it. No charges have been filed, and Trump has denied wrongdoing.

Debs’ key conviction and his 10-year sentence were upheld by the Supreme Court in an opinion written by Justice Oliver Wendell Holmes. Holmes eventually became one of the court’s biggest champions of free expression, but the Debs opinion is now seen as a low point in the protection of the First Amendment during wartime.

“He was in prison on free-speech principles,” Dreier said, noting that when prosecutors had trouble proving exactly what Debs said, he essentially admitted to it.

At his trial, Debs declared to the jury: “I have been accused of obstructing the war. I admit it. Gentlemen, I abhor war. I would oppose the war if I stood alone.”

Trump’s motivations in the New York hush money scheme that prompted his indictment this week seem considerably less pure, Dreier noted. “There are people that admire Trump,” he said, “but nobody thinks he’s going to prison on principle.”