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Donald Trump is facing an extreme sliding-doors scenario on Election Day. If he wins, he would have the power to single-handedly scuttle the federal criminal cases against him, be immune from prosecution while in office, and, thanks to the Supreme Court, have broad immunity from prosecution once — if — he leaves. If he loses, though, he will face criminal penalties that could leave him in command of a 70-square-foot prison cell for most of the rest of his life.
“He will be facing serious legal jeopardy if he loses. He knows that,” says Bennett Gershman, a professor of constitutional law at Pace Law School who served for a decade as a New York prosecutor. “It’s probably on his mind every day. He faces four very, very serious cases, in one of which he has already been convicted as a felon. The others are easily convictable.”
The minute it becomes clear that Trump has lost the election, his legal team will be preparing for the fight of a lifetime to keep him out of prison. “This defendant will use every means at his disposal to delay the outcome and complicate the adjudication,” says Martin Horn, a professor of corrections at John Jay College and the executive director of the New York State Sentencing Commission. “Who knows what legal maneuvers are available to him?”
Here is a look at where the four cases against Trump stand and how they might play out.
The New York Hush-Money Case
Trump’s first hurdle will come 21 days after the election on November 26, when New York justice Juan M. Merchan is scheduled to sentence him on the 34 counts of falsifying business records he was found guilty of this past May. The charges stem from hush-money payoffs he directed to be made to porn star Stormy Daniels in the runup to the 2016 election, in order to hide her story of an illicit affair a decade earlier.
Norm Eisen, a lawyer and author who served as counsel to House Democrats during Trump’s first impeachment, analyzed 10,000 similar cases in New York and concluded that given the particulars of his case — including the severity of the underlying crime, his lead role in the scheme, and his lack of contrition — Trump faces about a 50/50 chance of being sentenced to incarceration “with jail time of less than a year,” Eisen says.
Gershman thinks the odds are better than that and foresees a longer sentence. “I think he almost definitely will receive a prison sentence,” he says. “I could see Judge Merchan sentencing him to 24 months in jail.”
If he does receive a prison sentence, Trump will be entitled to appeal and, under state rules, the judge “can allow him to remain out on bail pending the outcome of an appeal,” Horn says. There’s little chance that the appeals will succeed in tossing Trump’s convictions, but they will certainly slow the wheels of justice. “His appeal could take a year or two,” guesses Matthew Seligman, a fellow at the Stanford Constitutional Law Center.
Gershman foresees a quicker process: “The bars would slam shut, I would say, in under a year.”
Georgia’s Election-Interference Case
Down in Atlanta, Trump faces another set of state charges. In 2023, he was indicted by Fulton County district attorney Fani Willis for his effort to subvert the 2020 election in Georgia, most infamously by calling the secretary of state Brad Raffensperger and asking him to “find 11,780 votes” to put him over the top against Joe Biden.
The case was headed for trial in 2024 but then stalled out after the lawyer for one of Trump’s co-conspirators alleged that Willis had been engaged in a romantic relationship with a co-prosecutor and asked that she be removed from the case. The judge presiding over the case, Scott McAfee, ruled that Willis could remain at the helm but allowed Trump’s team to appeal his decision. The next hearing in the matter is scheduled for December 5.
“I don’t think that she should be disqualified, but that’s up to the Georgia courts,” Seligman says. “What we know for certain is that that’s going to take a while. And I’ll also say that, you know, legal cases in Fulton County take a very, very, very long time. On the order of years.”
He points to the RICO case against the rapper Young Thug, which started in 2022 and whose ten-month jury-selection process was the longest in Georgia history. “This is a particular dynamic in Fulton County where there’s just a history of [RICO] cases taking a very, very long time. The wheels of justice turn very slowly in these sorts of cases.”
Given all the potential sources of delay, Seligman says he sees the Georgia case as “beyond the horizon.”
The Classified-Documents Case
In many experts’ estimation the most open-and-shut criminal case against Trump is the one he’s facing in federal court in Florida over his handling of classified documents after leaving the White House. In late 2022, Attorney General Merrick Garland appointed Jack Smith as special counsel to oversee the ongoing federal investigation, and in June 2023, Smith obtained a 37-count indictment against Trump centered on the ex-president’s retention of documents at Mar-a-Lago and allegations that he obstructed federal efforts to retrieve them.
Smith pushed for a trial to start this past July, but the Trump-appointed judge overseeing the case, Aileen Cannon, has consistently steered the case in Trump’s favor, sometimes via rulings whose shoddiness has astonished the legal community. Cannon delayed the start of the trial, then tossed the whole case on the grounds that Smith hadn’t been properly appointed as special counsel. She is now reportedly on a list of potential attorneys general, should Trump win.
Smith has appealed Cannon’s decision to the 11th Circuit Court of Appeals, where many experts expect him to prevail. “Her decision was off the wall,” Gershman says. “The precedents are so strong in favor of the special counsel that the case will be resuscitated.”
Assuming the appeals court does put the case back on track, onlookers speculate that the court would also remove Cannon from the case, having already dinged her for a bad call in an earlier ruling. Given her apparent bias, it would seem that Cannon is overdue for removal. But Mary McCord, a professor at Georgetown Law who formerly served as an acting assistant attorney general for national security, thinks that’s unlikely. “The special counsel is very reluctant to move for a judge to recuse,” she says. “The Department of Justice is really reluctant to do that unless a judge’s rulings become so one-sided and so wrong under the law. Otherwise it just looks like sour grapes. In a case with inherently political overtones, the department is going to be even more reluctant.”
Given the overwhelming evidence against Trump, a jury trial will likely result in Trump’s conviction, according to most legal experts. If that’s the case, he’s facing a prison term of many years. “This is a very serious case,” McCord says. “People frequently go to prison for mishandling classified information, and here you have an enormous volume of it. You also have two different types of obstruction of justice. So I think it’s entirely possible that there would be prison time.”
Under federal rules, Trump would likely be remanded into custody upon sentencing, rather than being allowed to remain free pending appeals as is common with state charges. “How long it takes to get there ranges from a year to a couple of years,” Seligman says.
For her part, McCord doubts that the judge will send Trump to prison, as much as he deserves it. “This is Judge Cannon,” she says. “Given the way she’s treated this case so far, I think she would probably find a way not to.”
Trump-appointed judges have skewed legal proceedings in his favor in another case, the biggest of them all, surrounding his efforts to overturn the 2020 election that culminated with the January 6, 2021, attack on the Capitol.
The January 6 Case
Last year, Smith indicted Trump on four counts, and the case was heading toward a March trial when Trump’s team delayed that schedule by filing an appeal claiming that, as a former president, he enjoyed immunity from prosecution. Though Trump was shut out in the D.C. Court of Appeals, the Supreme Court decided to hear the case, then delayed it for months. Then, in July, the court’s six conservative justices (three picked by Trump) declared to the shock and dismay of many legal observers that Trump’s claim was largely valid. The case was sent back down to trial judge Tanya Chutkan so that she could decide which of the charges should be thrown out under the Supreme Court’s new standard that “official” presidential acts are immune from prosecution. Smith subsequently tailored his case and submitted it to Chutkan, whose ruling is pending.
Despite this setback for the prosecution, legal observers I spoke to believe it’s virtually certain that some, even most, of the charges will stand. “I think Judge Chutkan will hold that there are some things clearly not done in his official capacity that he can be held accountable for criminally,” says McCord. “And he will take that up and go all the way up to the Supreme Court again.”
After wending its way up and down the court system, the case will eventually go ahead in a time frame that can only be guessed at. “This will go to trial,” says Seligman. “It’s just a question of whether that’s in 2025 or 2026 or 2027.”
And he will likely be convicted in Gershman’s opinion. “The charges are very, very strong,” he says.
The counts with the most severe penalties call for a maximum of 20 years’ incarceration. If he’s sentenced to prison, Trump would likely begin serving his sentence immediately. “Because of the gravity of the charges and the overwhelming evidence of guilt,” says Seligman, “I think that it’s much more likely that he would be remanded into custody during the pendency of his appeal.”
So if he’s not already serving time in a New York prison by then, Trump could find himself in a federal penitentiary as early as the end of next year.
The Wild Cards
Trump has spent a lifetime honing his skills at evading justice, and there are any number of maneuvers he could attempt to reduce his risk of prison time. One would be to seek a plea deal that would exchange an admission of guilt — and possibly a promise to stay out of politics — for a sentence that doesn’t include time behind bars. “That’s certainly what I would be recommending if I were his attorney,” McCord says. But Trump has always been extremely averse to admitting culpability.
Another escape route involves delaying the legal proceedings long enough that Trump’s lawyers could then argue that he is too old and infirm to stand trial. But he would have to be really far gone for that approach to work. “A stroke that leaves him unable to speak or communicate — that’s the level of incapacitation that would be necessary to avoid criminal proceedings,” Seligman says.
And then there’s the possibility that, having been sentenced to incarceration, Trump is allowed to serve that time in home confinement, perhaps within the confines of Mar-a-Lago or even while shuttling among his various estates. While that sounds pretty cushy, “after a few months — especially for somebody who’s used to traveling on a whim and going wherever they want to go — it gets punitive pretty quick,” Chris Maloney, a former chief U.S. probation officer, told Intelligencer earlier this year.
All told, barring his reelection, the odds are that Trump will find himself in some form of confinement at some point over the next few years. What his rise and fall will have shown is that while there are powerful forces within the justice system — some put there by Trump himself — to prevent a man of his station from facing the legal consequences of his actions, there are also other implacable forces at work to make sure that the law ultimately applies to everyone. And that, given enough time, the latter will prevail.
“Hopefully, at the end of the day, we can see that justice is done,” Gershman says. “We want the truth to come out. We want people to feel confident that the system works.”
