Could Trump Go to Prison? It’s Not Out of the Question

“I do think prison is a likely and appropriate punishment for the charges under consideration by the special counsel,” former White House lawyer Ty Cobb told The Messenger


Lawyers and ethicists are debating the unthinkable as the legal probes into Donald Trump plow forward: Whether the former president could eventually be sent to prison.

The chatter has only escalated in recent days, and for good reason. 

A New York judge on Tuesday set March 25, 2024, as the date for Trump to begin standing trial on charges surrounding alleged “hush money” payments to adult film actress Stormy Daniels during the 2016 White House campaign. In Georgia, Fulton County District Attorney Fani Wilis has signaled an August indictment of Trump is possible surrounding his conduct during the state’s certification of the 2020 election results. Special Counsel Jack Smith is also reportedly nearing the completion of at least one part of his multi-pronged federal investigation into Trump’s conduct in connection with the events of January 6 and the discovery of classified records in his Mar-a-Lago resort in Florida.  

While Trump is still a long way from being convicted, let alone sentenced, people who have worked for the current 2024 Republican presidential frontrunner say the prospects are increasing that Trump will be incarcerated as a result of at least one or more of the active criminal cases. 

Former U.S. President Donald Trump Visits Scotland
(Jeff J Mitchell/Getty Images)

“I do think prison is a likely and appropriate punishment for the charges under consideration by the special counsel,” Ty Cobb, a former Trump White House lawyer, told The Messenger. He said he expected the former president could wind up in federal prison for up to eight years if Smith’s probe leads to a conviction on Trump mishandling classified documents and defrauding the United States in his bid to hold onto the White House after the 2020 election. 

“What he did as president is so abhorrent to the Constitution, such a constitutional insult, that the laws they will be applying were never expected to be used against a president of the United States. And because they have to be used against a man who swore to uphold the Constitution while in the highest job in this land, they should be used forcefully as both punishment and a deterrent,” Cobb added.

Sending Trump to prison remains a deeply divisive subject among those who have been in his orbit, and among the many legal and security experts tracking his legal issues.

For starters, Trump is not any defendant. In reality he may have opportunities for plea deals, pardons or other means of sidestepping a prison sentence if he winds up in criminal court, legal experts told The Messenger. Even just the logistics of keeping a former president safe in prison would be immensely challenging, which could incline a judge to avoid a prison sentence altogether. 

“How do you put a president in jail? I don’t know. I don’t have an answer to the question,” said one former lawyer in the Manhattan D.A.’s office. “But my instinct says that judges would be disinclined to want to put a former president in jail, irrespective of the charge. To put Trump in jail would be very challenging from every standpoint.” 

A spokesman for Trump's campaign did not respond to a request for comment.

As part of The Messenger’s mission to highlight multiple views on complex topics, we’re going to unpack a few different perspectives over whether Trump could go to prison. Read them below.

Point of view: No one is above the law, not even a former president

Readers who follow Trump’s legal proceedings are familiar by now with the refrain: “No man is above the law.”

It’s an idea that gained real-life relevance with Richard Nixon during Watergate and then again during the Trump era. From Sen. Elizabeth Warren (D-Mass.) to former Trump fixer Michael Cohen and the ACLU, the argument goes that Trump needs to be treated fairly under the law in order for the rule of law to continue.

“We had a candidate who as a sitting president tried to use his power to stay in office even though he lost the election. If there is a strong case that he did it by illegal means, then he needs to be prosecuted for there to be the rule of law,” said Richard L. Hasen, director of UCLA Law’s Safeguarding Democracy Project.

This idea of fairness is not just a legal concept: It’s also necessary for maintaining a healthy democracy, said Rachel Kleinfeld, an expert on troubled democracies and fellow at the Carnegie Endowment for International Peace.

The judiciary’s responsibility to carry out the law is instrumental to keeping democracy functioning, Kleinfeld said.

“If a former president has committed crimes that seem likely to hold up in a court of law, and they’re serious crimes, we actually have to have a trial. Otherwise it would be violating the rule of law,” said Kleinfeld. “A president who is no longer in office can’t give up the law. That’s a monarchy.”

Lawyer George Conway, a prominent Trump critic, echoed Cobb in an interview with MSNBC’s Chris Hayes on Monday. Based on the information that’s available about the investigation, he argued the Justice Department’s Mar-A-Lago probe is a strong case that could warrant a prison sentence.

The fact that a federal judge in Washington D.C., was willing to pierce attorney-client privilege between Trump and his lawyer shows “the evidence is incredibly strong,” Conway said.

Point of view: “The system will break” before Trump goes to prison

Sentencing a former president to prison would be a first for the United States, and security experts cite logistical challenges as a reason they don’t believe it would ultimately happen. Trump’s allies warn that such a severe penalty would do damage to the country. 

“The system will break before Donald Trump goes to prison,” longtime Trump friend and former aide Michael Caputo told The Messenger.

For starters, it’s not clear yet if Trump will be convicted of crimes that would warrant prison time. 

Public information suggests additional criminal charges may be brought against Trump as early as this summer, but it’s still far from a certainty in any of the jurisdictions from federal court in Washington D.C. to Fulton County. It’s possible any of these cases against Trump would not result in convictions. Trump has pleaded not guilty in the New York case and denies having had sex with Daniels, whose real name is Stephanie Clifford. Trump's lawyers can be almost certain to file appeals, lots of them. And even if any indictments result in guilty verdicts, the judges in each case will have discretion as to how to mete out punishment. 

Fulton County District Attorney Fani Willis
Fulton County District Attorney Fani Willis (C) is investigating Trump over his actions around the 2020 presidential election. (Photo by Megan Varner/Getty Images)

In Georgia, Willis is reportedly weighing racketeering and corruption charges against the former president. If charged and convicted of these crimes under Georgia law, Trump could face a minimum five-year sentence, and up to 20 years, though some or all of the sentence could be probation. 

As for the New York trial relating to Trump’s hush money payments, each of the 34 felony counts comes with a maximum sentence of four years in prison. But even there, three legal experts told The Messenger they’re skeptical Trump would be locked up.

“It would be unusual and unexpected for him to go to jail,” said the lawyer who formerly worked for the Manhattan D.A.’s office. Based on currently available information, District Attorney Alvin Bragg’s strategy of using federal law to escalate charges to felonies is unusual, the lawyer said, and would likely be challenged extensively by Trump.

America also has a tradition of pardoning or brokering plea deals with former presidents in the name of national healing. Most famously, President Gerald Ford pardoned Nixon shortly after Nixon resigned from office. President Bill Clinton cut a deal with federal investigators ensuring he would not be indicted after the Monica Lewinsky scandal just hours before he left the White House.

Then there are complex practicalities. For one: A prison would need to ensure Trump’s safety while he is incarcerated, a challenge for one of the most recognizable people on earth.

High-profile inmates – like Martha Stewart, who spent five months in a West Virginia federal prison in 2004 – are generally sentenced to low-security facilities that put special procedures in place to monitor the inmate, said Donald Mihalek, who spent more than two decades in the Secret Service. That includes establishing regular check-ins, doctors visits and conducting threat assessments to keep the inmate safe.

As a former president, Trump is also legally entitled to lifetime protection from the U.S. Secret Service – and those protections can’t be waived by a judge or jury. The Secret Service has never had to protect a former president while in prison.

“The Secret Service works with stakeholders to protect all locations protectees go to,” said Mihalek. “That goes with combat zones, non combat zones– you name it.”

“But I can’t fathom that happening,” Mihalek added. “I think there’s a round agreement that, based on the current crime charged, nobody could see jail time extended to a former president.”

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