WASHINGTON — Former President Donald Trump has a massive personal stake in the upcoming election, which could either send him back to the White House -- or to a courtroom for what could be years of legal proceedings under the looming threat of incarceration.
No other presidential candidate in history has faced the possibility of such drastically different outcomes, in which Trump's legacy, personal fortune, and individual liberty could be decided by a few thousand swing state voters.
If he returns to the White House, Trump has vowed to fire Jack Smith, the special counsel who has brought two federal cases against him, "within two seconds"; he has said he would punish the prosecutors and judges overseeing his cases; and he will likely avoid serious consequences for any of the criminal charges he continues to face.
"If he wins, say goodbye to all the criminal cases," said Karen Friedman Agnifilo, who previously served as the chief of the Manhattan district attorney's trial division.
"The criminal cases are over, whether it's legally or practically," added Friedman Agnifilo, who said a Trump victory would be a "get out of jail free card" for the former president.
If he loses the election, Trump faces years of court proceedings, hundreds of millions in civil penalties, and the possibility of jail time, beginning with the sentencing for his New York criminal case on Nov. 26.
Here is what could happen in each of Trump's criminal cases.
New York hush money case
Trump's most pressing legal issue following the election is his Nov. 26 sentencing on 34 felony counts for falsifying business records to cover up a 2016 hush money payment to adult film actress Stormy Daniels.
Defense lawyers were able to successfully delay the sentencing twice -- first by asking to have the case dismissed based on presidential immunity and the second time by highlighting the political stakes of a pre-election sentencing. Describing Trump's case as one that "stands alone, in a unique place in this Nation's history," New York Judge Juan Merchan opted to delay the sentencing until November to ensure the jury's verdict would "be respected and addressed in a manner that is not diluted by the enormity of the upcoming presidential election."
While first-time offenders convicted of falsifying business records normally avoid incarceration, legal experts told ABC News that the unique factors of Trump's case -- including him being held in criminal contempt ten times and the finding that he falsified business records to influence an election -- could push Judge Merchan to impose some prison time. When ABC News surveyed 14 legal experts about Trump's sentence in June, five believed an incarceratory sentence was likely, two described the decision as a toss-up, and seven believed a prison sentence was unlikely.
The sentencing could still proceed in November if Trump wins the election, though the new circumstances could influence Judge Merchan's decision, according to Boston College law professor Jeffrey Cohen. Merchan could opt to impose a lighter sentence -- such as a day of probation -- or opt to delay the sentence until Trump leaves office.
"A sitting president wouldn't be forced to be incarcerated while they're serving their presidency, and so he could theoretically serve it once he's out of office," said Cohen, who noted that a delayed sentence could incentivize Trump to remain in office as long as possible.
"If he wins, I think realistically speaking, not there will be no meaningful sentence because of it," said Friedman Agnifilo.
Trump's lawyers could also attempt to delay the sentencing in light of the outcome of the election, and the former president still has multiple outstanding legal efforts to delay the case. On Nov. 12, Judge Merchan plans to issue a ruling on Trump's motion to throw out the case because of the Supreme Court's recent ruling granting him immunity from criminal prosecution for official acts undertaken as president -- and if Merchan denies that motion, Trump could attempt to immediately appeal it to try to delay the sentencing further.
Trump has also asked the U.S. Court of Appeals for the Second Circuit to move the state case into federal court, which his lawyers could use to prompt a delay of the sentencing. Unlike his federal cases -- for which Trump could theoretically pardon himself -- the state case will likely remain outside the reach of a presidential pardon, even if Trump successfully removes the case to federal court, according to Cohen.
Federal election interference case
In the shadow of the presidential race, U.S. District Judge Tanya Chutkan has been considering how Trump's federal election subversion case should proceed in light of the Supreme Court's immunity ruling, which delayed the case for nearly a year. Fifteen months after Trump pleaded not guilty to charges of undertaking a "criminal scheme" to overturn the results of the 2020 election, Judge Chutkan has set a schedule for the case that stretches beyond the election, with deadlines for key filings set for as late Dec. 19.
Trump has vowed to fire Smith if he's reelected, but that might not be necessary since long-standing DOJ policy bars the prosecution of a sitting president -- meaning the federal cases against Trump may be stopped immediately should Trump take office.
While Smith could attempt to continue his prosecution in the two months between the election and the inauguration, there's little he could do to revive the case, according to Pace University law professor Bennett Gershman.
"They can continue to do what they're doing, but it's not going to really matter if, at the end of the day, Trump is able to appoint an attorney general who will then make a motion to dismiss the charges," Gershman said.
While his federal case will inevitably go away if Trump wins, the exact way it happens is uncertain. Smith could attempt to issue a final report about his findings, Trump could face a standoff with Congress or the acting attorney general about firing Smith, or Judge Chutkan could push back against the Justice Department's eventual move to dismiss the charges.
If Trump loses the election, Judge Chutkan is expected to continue to assess whether any of the allegations in the case are protected by presidential immunity. Her final decision will likely be appealed and could return to the Supreme Court, likely delaying a trial for at least another year, according to experts.
Federal classified documents case
After U.S. District Judge Aileen Cannon dismissed Trump's criminal case for retaining classified documents and obstructing the government's efforts to retrieve them, Smith asked an appeals court to reinstate the case, arguing that Cannon's decision about the appointment and funding of special counsels could "jeopardize the longstanding operation of the Justice Department and call into question hundreds of appointments throughout the Executive Branch."
If Trump wins the election, prosecutors will likely have no choice but to withdraw their appeal, according to Friedman Agnifilo, cementing Judge Cannon's dismissal of the case.
If Trump loses the election, the case faces a long road before reaching a trial. Prosecutors need to successfully convince the Atlanta-based 11th U.S. Circuit Court of Appeals to reverse Cannon's dismissal, and Trump's team has already raised a defense based on presidential immunity, which could become the basis for a future appeal.
Faced with a series of adverse rulings, Smith would also face a key decision about whether to ask for Judge Cannon to be recused from the case, according to Cohen.
"I'm not sure what their reasons are now, except 'We don't really like what she's decided,'" said Cohen, who was skeptical about the government's grounds for recusal based on the trial record alone.
In a separate case overseen by Judge Cannon, defense lawyers for Ryan Routh -- the man accused of trying to assassinate Trump at his Florida golf course in September -- moved to have Cannon recused, in part citing ABC News' reporting that a personnel roster circulating through Trump's transition operation included Cannon's name among potential candidates for attorney general should Trump be reelected. Cannon on Tuesday rejected that motion, describing the argument about a potential appointment as "'rumors' and 'innuendos.'"
"We had a brave, brilliant judge in Florida. She's a brilliant judge, by the way. I don't know her. I never spoke to her. Never spoke to her. But we had a brave and very brilliant judge," Trump said about Cannon last week.
Fulton County election interference case
Trump's criminal case in Fulton County, Georgia, related to his effort to overturn the results of the 2020 election in that state, has been stalled since June while an appeals court considers the former president's challenge to Judge Scott McAfee's decision not to disqualify District Attorney Fani Willis for what McAfee called a "significant appearance of impropriety" stemming from a romantic relationship between Willis and a prosecutor on her staff. A Georgia appeals court scheduled oral arguments about whether Willis can continue her case on Dec. 6.
When asked about the future of the case if Trump wins the election, Trump defense attorney Steve Sadow told Judge McAfee last December that a trial would likely have to wait until after Trump completes his term in office.
Since August 2023, when Trump was charged in Fulton County with 13 criminal counts, Judge McAfee has chipped away at the indictment by tossing five of the counts with which Trump was originally charged.
If he loses the election, Trump could attempt to stall the case by continuing to push to have Willis disqualified or by mounting a presidential immunity defense.
"The indictment in this case charges President Trump for acts that lie at the heart of his official responsibilities as President," Trump's lawyers wrote in a January motion.