September will bring a swiveling of eyes to New York, where Judge Juan Merchan is set to make two decisions that could alter the trajectory of President Trump’s future — and America’s. Trump, though, could mount an unprecedented and lightning appeal to stop a prison sentence from being handed down.

On September 16 Judge Merchan is scheduled to rule on whether the Supreme Court’s landmark immunity decision in Trump v. United States upends the “guilty” verdicts brought in against the 45th president on 34 felony counts in the Manhattan hush-money case. Two days later, he will hand down a sentence against Trump for those convictions, one that could include prison time. 

Legal observers say a typical defendant with no priors would not be sentenced to incarceration, but Trump is no ordinary defendant and is deeply unpopular in Manhattan, where he only received 12 percent of the vote in the 2020 general election. He was recently levied financial judgments in two civil cases.

As for the hush-money case, all of Judge Merchan’s prior rulings in that case have been unfavorable to Trump, who has formally sought three times for the judge to recuse himself due to what the former president alleges is bias towards his enemies. Judge Merchan has refused his requests and has insisted on staying on the case.

Should Judge Merchan rule against Trump on the immunity issue, the 45th president could move to ensure that  the judge does not have the opportunity to hand down a sentence before November’s election, which is shaping up to be a tight contest. District Attorney Alvin Bragg has already signaled that he will not oppose such a request for delay. He wrote Judge Merchan that the People “defer to the Court on whether an adjournment is warranted to allow for orderly appellate litigation of that question.”

Both the district attorney and the former president are contemplating a situation where Judge Merchan rules against Trump on immunity. Such a decision would likely reckon that the acts for which the former president was convicted — hush-money payments to an adult film star, Stormy Daniels, whose real name is Stephanie Clifford — were not official acts, and therefore not entitled to the presumption of immunity granted by the Supreme Court. 

Mr. Bragg’s office has written Judge Merchan that the evidence that Trump claims is  “affected by the Supreme Court’s ruling constitutes only a sliver of the mountains of testimony and documentary proof that the jury considered in finding him guilty” and that “this case involved evidence of defendant’s personal conduct, not his official acts.” While Trump does not argue that the charged acts themselves are protected, he alleges that protected evidence made it sway before the jury and tainted the verdict.

The most persuasive refutation to Trump’s argument that the verdict ought to be overturned is that the payments, which were facilitated by the attorney Michael Cohen, were issued before the election. Trump, though, reimbursed Cohen from the White House. Mr. Bragg contends that the payments amounted to an effort to corruptly affect the vote, making the payments felonious. 

The district attorney, though, did adduce evidence from Trump’s presidency, like his interactions with two of his closest White House aides, Hope Hicks, who cried on the witness stand, and Madeleine Westerhout. The government referred to those colloquies as significant evidence in closing arguments.     

If Judge Merchan keeps the sentencing date — that is within his discretion  – and finds for the government that the convictions “exclusively stem from defendant’s ‘unofficial acts’ — conduct for which ‘there is no immunity,’” Trump will have to appeal in something like 48 hours if he wishes to avoid a sentence before the election. Such a request for review would normally be addressed first to the New York Appellate Division and then, potentially, to New York’s top state court, the Court of Appeals. After that, the United States Supreme Court could deign to hear an appeal invoking its own ruling in Trump. 

The rub is that New York’s criminal procedure mandates that convictions are only appealable after sentencing, not before. Empire State courts have not allowed what is called interlocutory, or intermediate, appeals, after conviction and before sentencing. Trump could have to turn to a federal district or appellate court for that intervention, on the basis of the high court’s ruling in Trump. Judge Merchan, though, could choose to moot the issue by delaying the sentencing pending appeal of the immunity issue — or the election.

Trump’s attorneys appear to have anticipated the tight turnaround time between the immunity ruling and sentencing when they asked Judge Merchan to delay sentencing. Earlier this month, they argued that a “single business day is an unreasonably short period of time for President Trump to seek to vindicate these rights, if he must.” Instead, they request “adequate time to assess and pursue state and federal appellate options in response to any adverse ruling.”

Those lawyers — Todd Blanche and Emil Bove — also dilated on the possibility of an interlocutory appeal delivered from the federal judiciary. They contend that “the Trump decision arose from an interlocutory appeal, while proceedings were stayed in the federal trial court, and the Supreme Court confirmed that a trial court’s denial of immunity’ is ‘appealable before trial.’” They reason that since Trump arose from an appeal from Judge Tanya Chutkan’s ruling, a denial of immunity ought to be “immediately appealable in a similar procedural posture.” 

That Mr. Bragg declined to take a position on scheduling suggests that the district attorney, an elected Democrat, could be aware of the political impact a sentencing could have on the tight presidential race. 

If Judge Merchan declines to prescribe prison, it could appear as a verdict from the bench on the flimsiness of the charges. If he does, Trump could make the kind of claims of political prosecution and persecution that appeared to bolster his fortunes when the verdict was brought in during the Republican primaries.   In the hours following his conviction in May, Trump raised $52 million for his campaign.

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This article has been updated from the bulldog