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The election calendar’s set. Trump’s trial timing? Deeply unclear.

Four judges, multiple appeals courts and ‘a completely unpredictable defendant’ add up to a trial schedule shrouded in uncertainty

Former president Donald Trump attends the Trump Organization's civil fraud trial in New York on Dec. 7. (David Dee Delgado/Pool/AP)
10 min

As Donald Trump prepares for somewhere between one and four criminal trials this year, the only thing certain about his court schedule is the profound uncertainty that hangs over all of it.

The diffuse nature of the U.S. court system, the uncharted legal territory of the cases against the former president and the roiling political debates around Trump’s 2024 presidential campaign all add to the lack of clarity.

Legal experts caution that the actions that will determine precisely when Trump goes on trial have yet to happen. Judges — two federal, two state — in four parts of the country often seem to be waiting for others to make key decisions, while Trump’s attorneys have launched a flurry of appeals that could delay proceedings. Federal prosecutors, in turn, have stressed urgency without providing a specific reason for the need for speed.

“It’s not like there’s one court system that can direct the sequence; there are four different jurisdictions” operating independently, said Leslie Caldwell, former head of the Justice Department’s criminal division. “And the closer you get to the election, the bigger a challenge it is, because it becomes not just trying your case in court, but also becoming part of the campaign story.”

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What’s clear is that primary voting will start before any of the criminal trials. The Iowa caucuses are on Monday, and the New Hampshire primary is a week later, with Trump as the Republican front-runner. Super Tuesday, the largest single day of primaries and the day that often reveals who the major-party nominees will be, is March 5. That is a day after the scheduled opening date of Trump’s first criminal trial, in Washington, but that trial may be delayed by ongoing appeals.

The March 4 case involves federal charges of conspiring to obstruct the 2020 election. Trump also faces federal charges in Florida of mishandling classified documents, state charges in New York related to 2016 hush money payments, and state charges in Georgia of trying to obstruct the 2020 election results there.

“There’s no way to predict all the moving pieces that is the Trump legal saga,” former federal prosecutor Jim Walden said. “In the history of mob prosecutions, I don’t think we ever saw an organized crime boss with four active criminal cases at the same time, and in Trump’s situation, it’s not just a matter of four cases and four judges.”

Walden described Trump as “a completely unpredictable defendant who is not motivated necessarily by vindication now as much as creating chaos so that he can eventually try to pardon himself if he’s lucky enough to eventually win the political contest.”

A judicial game of chicken

Multiple appellate courts are weighing pieces of the Trump prosecutions in ways that could drastically alter their courses.

People close to the former president, speaking on the condition of anonymity to describe private discussions, say his legal strategy is focused on the two federal cases brought by special counsel Jack Smith. And the central target of the Trump strategy on those two cases is to delay them until after the election, these people said.

The dynamic is a tricky one, the Trump advisers say. They want to push the trials back as far as they can — preferably to after the election — but they also do not want a September or October court date, particularly in the D.C. election-obstruction case. While Trump has viewed going to court as a political benefit and a fundraising mechanism in the GOP primaries, some of his political and legal advisers fear that the cases, and the damaging disclosures they are likely to bring, would be an albatross in a general election.

Trump’s team has spent months plotting how to combine the political calendar and the potential legal one. “You try to control what you can control, but with the courts, some of it is out of your hands,” one of Trump’s advisers said.

A Trump spokesman did not respond to requests for comment.

The U.S. Court of Appeals for the D.C. Circuit heard arguments Tuesday on whether the charges should be dismissed because of presidential immunity or double jeopardy claims. While that panel has sent signals that it intends to move quickly, the pretrial schedule is frozen until the appeal is resolved.

Those questions have never been directly addressed by the Supreme Court, which will probably have to decide the matter before Trump can be tried. Even assuming the high court allows the case to proceed, those deliberations could set the trial back by months.

The second federal case, in Florida on charges of mishandling national security documents and obstructing government efforts to retrieve them, is slated to begin in late May. But U.S. District Judge Aileen M. Cannon has set pretrial deadlines that make some lawyers skeptical the case will stay on schedule, particularly given the complex rules of classified evidence and Cannon’s relative lack of experience.

“Any judge applying any procedure is going to do it more efficiently the second time than the first time,” said David Aaron, a former federal prosecutor. The law for how to handle classified evidence “is so nuanced and such a niche part of the law that a judge may want to take her time doing it,” he said.

At a hearing last year in which Cannon expressed skepticism about the special counsel’s timeline for the trial, prosecutor Jay Bratt conceded: “We don’t know what is going to happen in this case. We don’t know what is going to happen in the D.C. case. … That trial date could disappear. We understand that.”

Like cars at a four-way stop sign, most of the judges overseeing Trump’s cases seem to be seeking cues from the others to know when to proceed with their own cases.

In court hearings in the Georgia state case, Judge Scott F. McAfee has signaled he is looking for a clear opening in Trump’s federal court calendar before picking a date for a sprawling trial with more than a dozen defendants that prosecutors say they expect will last four months. Trump filed an immunity-based appeal in that case last week.

1 in 4 Americans say they believe the FBI instigated Jan. 6 riot

All of which leaves a potential window for what many lawyers view as the least significant of the Trump criminal cases — the New York fraud charges surrounding 2016 hush money payments to an adult-film star — to go to trial first.

The indictment was the first one brought against Trump, in March of last year, and New York Supreme Court Justice Juan Merchan has set March 25 as the opening day for a trial.

But he has done little with the case over the past nine months. Merchan has scheduled a hearing in February that could reveal whether he plans to stick with the late March trial date — a decision that may well depend on the status of the appeal in Trump’s D.C. case.

Prosecutorial discretion

Walden, the former federal prosecutor, worries that the potential for confusion and delay surrounding the Trump trials could “wreck what’s left of the public’s view of the legitimacy of our law enforcement institutions and our courts, because in this whole saga, everyone’s got a political stake in either ensuring Donald Trump is vindicated or convicted.”

Justice Department policy has long held that within a few months of an election, the department should not take overt steps that could be seen as trying to affect the outcome of the vote. But that policy is not absolute and is meant primarily for indictments, searches and subpoenas — not a trial schedule imposed by a judge.

During the 2016 election, FBI officials were determined to reach a decision before the Democratic nominating convention on whether charges should be filed in the investigation of classified information found on a private email server used by presidential candidate Hillary Clinton. Those same FBI officials, however, decided 11 days before the general election to publicly reveal they had reopened the case.

While Trump’s legal team has made no secret of its desire to push the trials until after the election, the special counsel has argued for urgency in the two federal cases, without explicitly saying why.

In court filings, federal prosecutors have cited the “exceptional national importance” of a quick trial when it comes to the charges against Trump — but have not mentioned the presidential nominating contests or the general election on Nov. 5.

Legal experts say prosecutors’ reticence to mention the election or the politics intertwined in Trump’s cases is to be expected. Justice Department officials do not want to appear to be interfering in an election — but there’s also a public interest in knowing whether Trump is guilty or innocent before voters head to the polls, lawyers said.

“The unique situation that the Justice Department is in is an unprecedented one that no one ever expected. So there are no precise rules or traditions that cover this scenario,” said Aaron, the former federal prosecutor. “They are between a rock and a hard place on this.”

Dan Schwager, a former federal prosecutor who handled public corruption cases, pushed back against the claim frequently made by Trump and his attorneys — that the criminal prosecutions amount to election interference. The government frequently indicts politicians, he said, and the fact that Trump has been charged does not mean prosecutors are interfering in an election.

Still, even while handling political cases, prosecutors have a responsibility to ensure that their work does not stoke divisions unnecessarily.

In the Trump case, Schwager said, the public — and Trump himself — dissect every filing and court hearing. The former president and his allies often misconstrue what happened and make routine court proceedings seem politically explosive. In that context, Schwager said, it makes sense that prosecutors would be extra careful to avoid mentioning politics in proceedings.

“In part, it is because of how much spin and lies and hypocrisy” are disseminated by Trump and his supporters, said Schwager, who as a lawyer in private practice has also defended public officials accused of wrongdoing. “What prosecutors try to do is stay away from inflaming public passions — I think Jack Smith has done an incredibly good job of staying away from that while speaking in court in forceful, but tame, ways.”

None of the 2024 election milestones — the primaries, the conventions or 90 days before the general election — are likely to serve as stop signs for a criminal trial, according to current and former law enforcement officials.

But as each of those milestones is reached, the risk and difficulty of conducting a trial increases, the current and former officials said. And it’s unclear how those concerns might weigh on the judges overseeing the cases.

More on the Trump Jan. 6 indictment

The charges: Former president Donald Trump pleaded not guilty to charges that he plotted to overturn the 2020 election in the run-up to the Jan. 6, 2021, attack on the U.S. Capitol. Here’s a breakdown of the charges against Trump and what they mean, and things that stand out from the Trump indictment. Read the full text of the 45-page indictment.

The trial: Jury selection in the D.C. criminal trial is set to begin Feb. 9, with the trial set to begin March 4. U.S. District Judge Tanya S. Chutkan has imposed a gag order on Trump’s public statements in advance of the trial.

The case: The special counsel’s office has been investigating whether Trump or those close to him violated the law by interfering with the lawful transfer of power after the 2020 presidential election or with Congress’s confirmation of the results on Jan. 6, 2021. It is one of several ongoing investigations involving Trump.

Can Trump still run for president? While it has never been attempted by a candidate from a major party before, Trump is allowed to run for president while under indictment in four separate cases — or even if he is convicted of a crime. Here’s how Trump’s indictment could affect the 2024 election.