Donald Trump has several legal tactics to try to stay out of state prison, but his best chance of success turns on the outcome of the presidential election.
The former president has already twice successfully delayed his sentencing past Election Day on 34 felony counts of falsifying business records to influence the 2016 election by hiding a hush money payment to Stormy Daniels. His lawyers are gearing up for more legal fights ahead, but no tactic will influence his future more than how voters cast their ballots.
“It’s 50/50” that he gets sentenced in November, said Karen Friedman Agnifilo, a former top official at the Manhattan district attorney’s office and a CNN legal analyst. “If he loses the election, I think he gets sentenced, and I think he gets sentenced to prison. If he wins, I don’t think this goes forward.”
A victory on Election Day, she added, is “his get out of jail free card.”
For years, Trump’s legal playbook has been to seek delays. Often, he’s been successful. He was facing four criminal indictments by late 2023 and only one of those cases went to trial before the election.
Now his lawyers are sketching out several tactics to postpone his sentencing, currently scheduled for November 26, whether he wins or loses the presidential election. How the courts handle these last-ditch efforts will dictate an unprecedented moment in American history and whether and when a former US president serves time in prison.
“The uniqueness of this entire situation is beyond anything any founding father could have ever contemplated,” said retired New York state Judge Jill Konviser. “There’s no playbook here. You can’t look this up in a law book and find an answer to the query because it doesn’t exist.”
Previously, prosecutors have not objected to Trump’s bids to delay his sentencing before the election, which Judge Juan Merchan noted in agreeing to postpone Trump’s sentencing until late November. It isn’t clear what position prosecutors will take once all the votes are counted.
Immunity and removal
Merchan, who oversaw the hush money trial, said he will decide on November 12 – one week after Election Day – Trump’s motion to dismiss his conviction in light of the US Supreme Court’s decision on presidential immunity that limits what evidence can come before a jury.
If Merchan grants Trump’s motion, the charges would be dismissed, and he would not be sentenced.
If Trump loses on immunity, his lawyers are expected to ask Merchan to delay Trump’s sentencing so they can appeal. And if that’s not granted, his attorneys are planning to appeal the immunity decision to state appellate courts and potentially all the way to the US Supreme Court to ask the courts to delay Trump’s sentencing until all appeals are exhausted, which could take months.
Simultaneously, Trump is trying to move the hush money case out of state court and into federal court, where he thinks he has a better shot at an appeal.
Trump’s attorneys attempted this in 2023, and District Judge Alvin Hellerstein denied it. But following the Supreme Court ruling, Trump’s attorneys made a second attempt this summer. Hellerstein denied that request, too, finding Trump didn’t show “good cause” for why he should reconsider his 2023 ruling. He wrote, “Nothing in the Supreme Court’s opinion affects my previous conclusion that the hush money payments were private, unofficial acts, outside the bounds of executive authority.”
Trump’s attorneys appealed that ruling and the Manhattan district attorney’s office has three months to respond. The window provides Trump’s lawyers another avenue to try to move the sentence by arguing that Merchan can’t sentence Trump while an appeal on a question of removal is outstanding.
Their argument will hinge on a line in the law that says final judgment, in this case the sentencing, cannot proceed if a notice of removal is pending.
Federal law states that, “The filing of a notice of removal of a criminal prosecution shall not prevent the State court in which such prosecution is pending from proceeding further, except that a judgment of conviction shall not be entered unless the prosecution is first remanded.”
In previous court filings opposing an earlier effort to delay his sentencing, prosecutors argued that there isn’t a valid notice of removal pending because the judge found Trump didn’t have “good cause” to make one.
“But the district court did not enter a remand order here because defendant never filed a proper notice of removal,” the district attorney’s office wrote in September. At the time, Trump was trying to get the federal appeals court to delay or “stay” his sentencing so he could appeal the district court’s ruling. That was denied when Merchan agreed to postpone Trump’s sentencing.
Prosecutors wrote in September that sending the case back to Hellerstein would restore Trump’s motion seeking permission to ask for removal and not turn it into a notice of removal. “The mere pendency of such a motion neither removes the state criminal case nor stays any aspect of the state criminal proceeding. Only a properly filed notice of removal could have such effects.”
Mixed outcomes
If Trump wins the race for the White House but loses his argument to dismiss the case, then his attorneys are likely to shape their legal arguments about constitutional issues and challenge whether a state judge could sentence a former president and president-elect, which could tie the case up in courts for years.
In addition, they are likely to argue that Trump shouldn’t be sentenced until after his term is completed – four years from January.
If Trump loses the election and his effort to overturn his conviction, his lawyers will likely make similar legal arguments to keep him out of prison, but whether they carry the same weight with courts could be different if Trump is a convicted felon without the protections of the presidency.
And without the shield of the White House, Trump could face trial in his other criminal cases, including the Washington, DC, federal election subversion case. If Trump wins, his Justice Department is expected drop that case altogether.
Sentencing day
Sentencing a former president or potential president-elect has never happened before in American history, putting Merchan in a unique position if it does go forward.
“When you’re in the middle of a high-profile media case, everybody is watching you,” said Diane Kiesel, a retired New York Supreme Court judge who served alongside Merchan. “But you don’t want to change what your approach to handling the case would be just because everybody is watching you.”
“You want to be sure, for lack of a better phrase, that you’re not playing to the cameras. You’ve got to step back a lot and say to yourself, “Am I doing here what I would be doing if there were three people in the courtroom?’” said Kiesel.
Merchan could sentence Trump to no time, probation, conditional release, or prison. Trump faces between 1-1/3 to 4 years in state prison on each count, which is capped at 20 years. During the criminal trial, Trump violated the judge’s gag order 10 times, which is something he can take into consideration.
“Sentencing is hard for judges,” Konviser said. “Some judges have reputations as tough sentencers and some have reputations as lenient sentencers and it’s just my opinion that Judge Merchan is neither. He would fall into the middle: harsh where it should be and lenient where it should be,” she added.
As a senior citizen with no previous convictions, Trump’s lawyers are expected to argue that he should not be sentenced to prison. It’s unclear what position Manhattan District Attorney Alvin Bragg, a Democrat, will take.
“It’s just really difficult for Bragg, prosecutorially and politically, to bring this charge, get a conviction and then say, ‘But we’re fine with no prison time,’” said Elie Honig, a CNN senior legal analyst and former state and federal prosecutor. “I think it’s substantially more likely than not that Bragg asks for prison.”
If Trump is sentenced to incarceration, under New York law, he would ordinarily be taken into custody immediately. Convicted felons are housed at New York’s notorious city jail, Rikers Island, where sentences of less than one year are served. For longer sentences, they often are housed temporarily at Rikers until they are transferred to the prison they’re assigned to serve longer sentences.
That raises additional questions about US Secret Service protection for Trump, whether as president-elect or a former president.
How Trump’s lawyers would respond to jail time
If a prison sentence is handed down, Trump’s lawyers are expected to immediately ask Merchan to let Trump stay out of lockup in a secured location in the courthouse, so he can appeal the verdict and sentence, among other issues. It would be up to Merchan to decide whether to grant that, and if not, Trump’s attorneys could race to the state appellate courts to seek an emergency stay of the sentence.
Honig said it was likely that Trump would be granted bail pending appeal – and suggested the district attorney’s office might even agree to such a condition if the judge imposes a jail sentence.
“Prosecutors do sometimes agree to it and say, ‘Look, there’s reasons to let this person do his appeal first, and then make him serve the sentence if he loses,’” Honig said.
If the sentencing date is not moved, the courts could decide that Trump, if he’s elected, could begin serving the sentence after his term is up, when he will be 82.
And if Trump is successful at delaying his sentencing day indefinitely, it could be the ultimate coup for his legal strategy. But some lawyers say it would send the wrong message.
“Nobody is supposed to be above the law,” Agnifilo said. “I think it would certainly send a message to people that certain people are above the law, and you can get away with things if you are powerful enough.”
