CNN  — 

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.”