Trump’s Appeal Could Deliver Him a Huge October Surprise

Donald Trump has vowed to appeal his historic criminal conviction in New York City, but the awkward timing means a final decision might not come until days before the November election—tossing a flaming catalyst into an already combustible situation.

Trump could be forced to spend time in a state prison, have his movements narrowly controlled on probation, or even be ordered to engage in community service over the summer—long before a higher court might overturn the first conviction of a former president. The alternative is that he remains out pending an appeal, with the judgment hanging over his head as he nears Election Day.

The irony is that Trump—who has always employed delay tactics to slow down the many legal actions against him, for sexually abusing a journalist, defrauding banks, faking business records, and so much more—could get a taste of his own medicine thanks to the bureaucratic New York court system.

“We’re gonna be appealing this scam,” Trump railed last week inside Trump Tower, just before calling the judge “a tyrant.”

He was talking about New York Supreme Court Justice Juan Merchan, who oversaw the seven-week trial that ended with a jury unanimously finding Trump guilty of all 34 felony counts of faking business records to pull off a cover-up.

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Merchan set sentencing for July 11, just three days past the First Judicial Department deadline to receive the basic appeal paperwork. The appellate division’s calendar shows that the soonest it can schedule oral arguments is Oct. 1, giving those judges only a few weeks to consider the case before voters go to the polls.

“There’s no avenue to get to the appellate court until there’s a judgment of conviction. And the judgment of conviction is entered when he’s sentenced,” said Jill Konviser, a retired New York criminal court judge.

It’s difficult to see how to speed that up. Appellate judges are on their summer break. The First Department doesn’t hear arguments in June, July, or August.

“In general, appellate work can move very slowly and deliberately. Nobody is generally in a rush to decide matters unless it’s something like a voting matter,” said Alan David Marrus, another former New York state judge.

Marrus noted that appellate courts sometimes expedite cases when considering election laws, like issues that relate to voter access, districting, or candidate qualifications. But while the conclusion to Trump’s case could certainly affect how some people vote, it’s not strictly an election matter.

Then there’s the likelihood that Trump will pull off the same trick as his former White House chief strategist, the right-wing media personality Steve Bannon, who was convicted by a jury of criminal contempt for ignoring a congressional subpoena but managed to stay out of prison for two years until being ordered behind bars this month.

Trump’s fate is certainly a matter of political exigency. But it lacks legal urgency, noted Marrus, who was chief of the appeals bureau at the Bronx District Attorney’s Office before becoming a judge in 1983.

“In a criminal case, the defendants get a stay of judgment if the court thinks there’s a real issue,” Marrus said. “I don’t know what’s going to happen with the Trump case. I’m assuming he’s not going to be in jail while this appeal is being heard. So, what’s the urgency to decide this case? You tell me. Why would they rush to decide this case?”

In reality, it’s up to Trump’s own legal team. And that’s where—once again—Trump could drag his feet. In his two federal trials against the journalist E. Jean Carroll, both of which he lost, Trump slow-walked every step of the rape defamation cases in an attempt to hold off on handing over the $88 million he owes her. He’s currently appealing a state court’s bank fraud judgment pegged at nearly $500 million, one that allows the New York Attorney General to seize Trump properties.

This criminal conviction is no different, Marrus noted. While Trump loves to tout how he packed the U.S. Supreme Court with three conservatives, tilting it rightward 6-3, he’ll first have to contest with an appellate court that oversees Manhattan—and is made up of judges from the same progressive metropolis Trump keeps bashing.

“The lawyers can work as diligently as they want to. But I don’t see them rushing it,” Marrus said. “I don’t think they’re expecting to win in the appellate division. If this case were going to the Supreme Court, I can see them wanting to get this right away. But the First Department has it now, and these are the same kinds of judges who were on the trial bench. They’re of the same mold: Elected and mostly Democrats from the New York area.”

Former prosecutor Tess Cohen said there’s certainly an impetus for Trump to try to speed up the appeal. She said Trump is likely to start serving a sentence—whether that’s at New York City’s dreaded Rikers Island jail or even a conditional freedom with strict rules attached. And while prison time could theoretically be put on pause by Justice Merchan or even an emergency stay from the appellate division, she said it isn’t likely.

“It’s almost never done. That’s a really rare thing. You basically have to have a very good chance at winning on appeal,” she said.

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Asked whether Merchan seems amenable to that—after watching Trump violate his gag order 10 times over, intimidate jurors, threaten the prosecutor, and even launch verbal attacks against the judge’s daughter—Cohen answered point blank.

“Not even remotely. And there’s no reason for him to. No standard defendant would get a stay pending appeal after a trial like this.”

In some ways, Trump spun this tangled web himself. The trial was scheduled to start on March 25, but was pushed back three weeks after some last-minute legal maneuvering by Trump’s defense team. Had the seven-week trial ended in mid-May, sentencing could have been set for mid-June, allowing Trump to argue for an appeal in September.

Instead, it’s possible Trump will head to the polls against President Joe Biden while his conviction is under appeal—giving MAGA apologists a lame-but-real excuse to say the judgment has not been finalized.

And if the First Department does issue an opinion cementing Trump’s fate by swiftly affirming the case in October? Cohen thinks Merchan is likely to push off the final court hearing until after the Nov. 5 election—raising the stark possibility that the judge who sentenced a former president might have to punish a president-elect.

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