Democrats perturbed about Donald Trump’s lead in 2024 polling have long had a comforting hope to fall back on: that Trump, who is facing four criminal prosecutions, will likely become a convicted felon before election day — or even be sent to prison.
That’s still possible — but it’s not as sure a bet as it once seemed.
Delays have piled up in federal court proceedings in the District of Columbia case about Trump’s attempt to steal the 2020 election and the Florida classified documents case against Trump, making it unclear whether either case will go to trial before November. (For the DC case, the hold-up is higher-court appeals; for Florida, it’s a slow-walking judge.)
Meanwhile, the Georgia election case has recently been consumed by scandalous allegations about Fulton County District Attorney Fani Willis, which throw the future of that prosecution into question. A judge will soon consider whether Willis and her office should be disqualified. He could decide not to do that, but even then, a trial date has not yet been set in the complex case.
That leaves the New York hush money case as the only trial that still seems on track. It’s currently scheduled to begin on March 25 — but first, on February 15, a judge will consider whether the felony charges against Trump there are legal.
The upshot is that Trump’s only trial this year could end up being the New York one — the least substantively significant of the four. The charges are about whether Trump improperly logged Trump Organization payments to his then-attorney Michael Cohen as legal expenses, when they were reimbursements for hush money Cohen paid Stormy Daniels. It’s shady behavior, but it’s not exactly at the level of stealing an election or jeopardizing national security secrets.
Yet there’s little that can be done to expedite things at this point. Prosecutors filed their cases last year, but now, they’re in judges’ hands — and judges are not beholden to the election calendar.
It’s not certain that even multiple Trump convictions would be the game-changer in the polls Democrats hoped for. But getting a verdict before November 5 is the only way we’d ever come close to finding out. (As to whether Trump might be sentenced to prison, we can’t know that until an actual trial takes place.)
So Election Day could come and go with most of Trump’s legal jeopardy unresolved — and, if he wins, some of those delays could become permanent, since he’d almost surely shut down the federal investigations targeting him.
Fani Willis is facing allegations in Georgia
Fulton County District Attorney Fani Willis arrives to speak at a news conference at the Fulton County Government building on August 14, 2023, in Atlanta, Georgia. Joe Raedle/Getty
Until recently, the sweeping racketeering case against Trump and 18 co-defendants filed by Willis’s office last August seemed to be notching win after win. The case was lauded by many in the press as the most comprehensive attempt to hold Trump accountable for trying to steal the 2020 election. And though a trial date had not yet been set, four of those co-defendants, including former Trump attorneys Sidney Powell and Jenna Ellis, had already pleaded guilty.
But earlier this month, an attorney for another co-defendant, former Trump campaign aide Mike Roman, made some explosive allegations in a court filing.
These allegations center on the claim that Willis has been having a “clandestine personal relationship” with a special prosecutor she had brought on to the case, Nathan Wade. That alone would not seem to be disqualifying. But Roman’s attorney alleges several improprieties about Wade’s role, including that he was unqualified for the job (his prosecutorial exprience is very thin), that Willis overpaid him, and that he then paid for vacations they took together.
Some legal experts have said these allegations are not a big deal. Others are more concerned. “If her choices to extend or prolong the investigation benefit a romantic partner, who is paying for her meals and vacations, that is an actual conflict,” Georgia defense attorney Andrew Fleischman writes in the Daily Beast. “Willis needs to level with the public, and she needs to do it fast,” former federal prosecutor Ankush Khardori writes in Politico Magazine.
Willis has not yet directly addressed these claims — but Judge Scott McAfee has told her to respond by Thursday. If McAfee decides there is impropriety here, he can disqualify Willis’s office from prosecuting the case. If that happens, the Prosecuting Attorneys’ Council of Georgia would get to choose a replacement prosecutor — and the path forward for the case would depend on whom they choose.
But, needless to say, the prosecutor getting tossed would not be a good sign for getting this case tried before election day.
DC trial preparation is on hold while higher courts decide on presidential immunity
This combination of pictures shows special counsel Jack Smith in Washington, DC, on August 1, 2023, and Trump in Palm Beach, Florida, on November 8, 2022. Saul Loeb and Eva Marie Uzcategui/AFP/Getty
The federal prosecution against Trump for trying to steal the 2020 election was brought by special counsel Jack Smith in Washington, DC. And Judge Tanya Chutkan seemed to be moving ahead quickly, with a trial date of March 4.
In pretrial motions, however, Trump’s attorneys put forward a defense: that he couldn’t be prosecuted for what he did between November 2020 and January 6, 2021, because has president — and a sitting president, they claim, should be absolutely immune from prosecution for actions that related to his official conduct while he was in office.
Judge Chutkan rejected that argument in an early December ruling, but Trump’s attorneys appealed to the DC Circuit. And, importantly, while the appeal is pending, Chutkan decided (in accordance with the law) to pause pretrial preparations. That stay was issued on December 13 — more than a month and a half ago.
The first stop in the appeal process is before a three-judge panel of the DC Circuit Court of Appeals. Arguments before that panel took place on January 9, but they have not yet issued their ruling. If they side against Trump, as expected, he could ask the full DC Circuit Court to hear the case — and then, inevitably, the Supreme Court.
In December, Smith tried to move this process along by asking the Supreme Court to consider the immunity question right away — but the justices declined to do so.
How long this will all take to shake out is anyone’s guess. But the longer each step in the process takes, the more the date for the trial will slip.
Judge Aileen Cannon has slowed the Florida case to a crawl
Judge Aileen Cannon United States District Court for the Southern District of Florida
Delays have also plagued Smith’s prosecution of Trump for mishandling classified documents in Florida. Here, the holdup is not higher-court appeals, but the district court judge assigned to handle the case: Aileen Cannon.
Cannon, a Trump appointee, has courted controversy on this case since before the former president was even indicted. After the FBI’s 2022 searches at Mar-a-Lago, Trump sued to try and block the government from reviewing some seized documents. Cannon heard the suit, and her conduct shocked legal observers, when she contorted the law in various rulings in Trump’s favor. A three-judge appeals court panel eventually reined her in in what the National Law Journal called “a rebuke.” (Two of those judges were themselves Trump appointees; the third is a hardline conservative appointed by George W. Bush.)
So it was of course great news for Trump that, when the special counsel indicted him last June, Cannon got the case. Initially, she didn’t seem to blatantly be going out of her way to help Trump — she set a May 20, 2024, trial date. It was, however, widely understood that this date might slip due to the need to settle complex issues about how the classified information at issue was to be handled and shared with Trump’s legal team.
The problem is that since then, Cannon has appeared to be in no hurry whatsoever to resolve these issues. By November, Politico’s Josh Gerstein wrote that Cannon was “slowing down the case,” saying she “has postponed key pretrial deadlines, and she has added further slack into the schedule simply by taking her time to resolve some fairly straightforward matters.” For instance, Cannon moved one hearing about how the classified documents at issue would be redacted from October to February — a four-month delay.
Things haven’t improved lately. Two weeks ago, Dennis Aftergut and Laurence Tribe argued in Slate that Cannon was continuing to demonstrate a “pattern” of “laying the groundwork for delaying Trump’s trial — until it’s too late for a jury to be empaneled and the case tried to verdict before the election.” No one seems to believe at this point that this trial will actually happen in May, and there are real doubts about whether it will happen this year at all.
The New York trial is still on track — but a judge will soon consider whether the charges will stand
Manhattan District Attorney Alvin Bragg speaks during a news conference following an arraignment of Trump on April 4, 2023, in New York City. Kena Betancur/Getty
When Manhattan District Attorney Alvin Bragg indicted Trump for falsifying business records last March, he faced a good deal of skepticism from national legal commentators about both the strength of the case and whether his decision to charge Trump was politicized. It’s also the least substantively important of the four prosecutions.
So naturally, this is the only trial that seems like it will happen anytime soon.
Last year, Judge Juan Merchan set the trial date for March 25, 2024. But he openly acknowledged he might move that date, to let Trump’s federal prosecutions get priority to go first. With the delays in those other prosecutions, though, New York seems like the best bet to go first after all.
There is just one hurdle first: On February 15, Merchan will hold a hearing at which he’ll consider Trump’s pretrial motions. And in those motions, Trump has raised many of the same doubts that outside legal commentators — and a former top prosecutor in the district attorney’s office — had about the charges.
Specifically, there’s been much debate over whether Bragg was on firm ground to charge the 34 falsifying business record counts against Trump as felonies, rather than misdemeanors. (Misdemeanor charges would not come with the possibility of prison time and would not make Trump a convicted felon.)
To charge felonies, Bragg must assert that Trump falsified business records — specifically, that he categorized reimbursements to Michael Cohen for Stormy Daniels’s hush money as legal expenses — with the intent to commit or conceal “another crime.”
The problem is: What crime?
Violating federal campaign finance law seemed like the clearest fit, but it involved federal and not state law, and existing case law was unclear about whether a state prosecutor could use federal law to justify this felony enhancement. Another potential federal crime, dodging taxes, had the same issue. A third possibility was a state law about unlawfully conspiring to promote an election candidate — but does state law apply to a federal presidential election?
This question bedeviled Mark Pomerantz, who was a lead prosecutor of the district attorney’s case before resigning shortly after Bragg took office. Pomerantz wrote about his worries in a book written before the indictment last year, opining that no specific “other crime” seemed to be a slam dunk guaranteed to survive judicial scrutiny. He said he hoped Bragg would charge the case anyway, but, he said, there would be a risk “that the charge will be reduced to a misdemeanor before a jury even hears it.”
Trump’s pretrial motions cite all these objections (and repeatedly cite Pomerantz’s book). “Even the most ardent and publicly supportive former prosecutor, Mark Pomerantz, to have worked on the case doubted that DANY’s legal theory is viable,” his attorneys wrote. Bragg’s team, for their part, claims that they don’t need to be specific — that they only need to establish “general intent” to commit or conceal a crime. However, they also argue that all of the crimes mentioned above apply.
So on February 15, these matters will finally be addressed at a hearing from Judge Juan Merchan. If Merchan lets the felony charges stand, Trump could then appeal. But one problem would be that he’d be appealing in New York state court, where few judges are likely to be particularly sympathetic to him. Bragg’s charges may well survive. And, flawed as it is, the New York case seems to be the best bet remaining for a Trump conviction before the election.
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