This could have been a year of court reckoning for Trump. Judges had other ideas

The indictment charging Donald Trump with hoarding classified documents leveled one jaw-dropping allegation after another, including that he showed off a secret Pentagon attack plan to guests at his golf club and suggested his lawyer mislead the FBI about the presence of the White House records.

But those details proved beside the point to the Trump-appointed judge presiding over the prosecution, who dismissed the case on grounds that the special counsel who brought it was unlawfully put in the job.

A separate criminal case accusing Trump of conspiring to overturn the outcome of the 2020 election seemed an opportunity for a trial this year focused on Trump’s failed effort to retain power after his loss to Democrat Joe Biden.

But the Supreme Court erased that possibility with an opinion that granted former presidents expansive immunity from prosecution.

A year that began with the prospect of a federal court reckoning for Trump will end without any chance of a trial, leaving voters without the finality of an up-or-down jury verdict in the two most consequential cases against the Republican presidential nominee. Yet both cases still loom over the election, their potential resurgence in the coming months making clear that at stake on Nov. 5 is not only the presidency but also possibly Trump’s liberty.

If Trump loses to Democrat Kamala Harris, he is at risk of trial and possible conviction in the classified documents case, assuming a federal appeals court revives it, or in the election interference case, where prosecutors issued a new indictment after the Supreme Court’s immunity opinion.

If Trump wins the White House, his attorney general could end both cases, and an already delayed sentencing in his state hush money case in New York — his only prosecution to reach a jury and end with a conviction — will be in even further flux.

That neither federal case made it to trial despite being brought well over a year ago highlights the complexities of prosecuting a former president and represents a vindication of sorts of the Trump team’s strategy of delay. It’s also a reflection of the immense hurdles prosecutors encountered before Republican-appointed judges, some of them selected by Trump, who in one case articulated a hugely expansive and novel view of presidential power and in the other appeared deeply skeptical of the prosecution’s premise well before derailing it.

“The reality is that efforts to hold the former president legally accountable (before the election), independent of the realm of politics, have failed in a wide variety of venues for a wide variety of reasons,” said Temple University law professor Craig Green.

“And what that means is it’s up to the American people” — not the courts — “what they have in mind for their future president.”

The Florida dismissal

The dismissal of the classified documents indictment was especially stunning because the case was seen inside the Justice Department and by legal experts as the most legally straightforward of the Trump prosecutions. Unlike the election interference case, it concerned behavior that occurred after Trump had left office in January 2021 and for which federal prosecutions are routine.

The outcome followed nearly two years of tensions between prosecutors and Aileen Cannon, a federal judge in Fort Pierce, Florida, with scant trial experience whose relationship with special counsel Jack Smith’s team had long ago soured and whose willingness to entertain all manner of motions by Trump’s defense lawyers had snarled the case before its eventual dismissal.

An indication of just how far afield the case had strayed from core factual issues was evident during a June hearing where Cannon occupied herself with the so-called Reno Regulations, the Ethics in Government Act and an esoteric legal principle, the “de facto officer doctrine.”

By day’s end, the government’s simmering exasperation had boiled over, with prosecutor David Harbach complaining that because of Cannon’s persistent questions, he’d been able to make only one of his points.

“Mr. Harbach,” she snapped. “I don’t appreciate your tone. I think we’ve been here before, and I would expect decorum in this courtroom at all times.”

The hearing ended without a ruling.

But three weeks later, and two days after Trump survived an assassination attempt at a campaign rally in Pennsylvania, Cannon dismissed the case. Siding with Trump’s arguments, she ruled that Smith had been appointed illegally by Attorney General Merrick Garland and should have been subject to confirmation by the Senate. Smith appealed, calling Cannon’s ruling contrary to decades of precedent.

It’s unclear how long it will take for the appeal to resolve, but if Cannon’s opinion is overturned and Trump loses the election, prosecutors would be able to resurrect compelling evidence accrued during the investigation.

That includes an audio recording of Trump boasting of a sensitive document he said he knew was classified and security camera footage showing boxes of records being moved from a storage room at Mar-a-Lago, his Florida home, days before investigators came to collect documents. When that June 2022 visit occurred, a Trump lawyer handed over a single folder even though boxes of files remained at the property.

That August, the FBI recovered 11 sets of classified documents during a search of Mar-a-Lago, an action that followed heated disagreements between FBI and Justice Department officials focused less on the strength of the evidence and more on whether it was the appropriate investigative step.

Trump has maintained he did nothing wrong by retaining records from his presidency.

The investigation was far along by the time Smith, a war crimes prosecutor in The Hague and a known commodity inside the Justice Department who’d been brought in more than a decade earlier to lead its public corruption section, was appointed by Garland in November 2022.

Once on the job, Smith took steps to press the case toward indictment — his team successfully argued before a federal appeals court to secure grand jury testimony from a lead Trump lawyer, M. Evan Corcoran, whose cooperation Trump had sought to block by invoking attorney-client privilege.

Though Trump’s legal peril had long been clear, one late surprise surfaced when prosecutors began presenting evidence to a grand jury in Florida — rather than the one in Washington they had been using — to obtain the indictment. After all, the documents were found in Florida and indicting the case there would avert a court fight over proper venue.

The decision carried significant risk.

Before the indictment was unsealed, word came that the case had been assigned — randomly, the court clerk said — to Cannon.

It was an unwelcome development for a Justice Department that had tangled with her a year earlier when she ruled in favor of Trump’s request for an independent arbiter to review the records seized by the FBI. That order was overturned by a unanimous federal appeals panel after prosecutors vigorously objected.

The fraught dynamic resumed where it had left off as prosecutors’ desire for a trial collided with Cannon’s deliberative, often quixotic, style that permitted drawn-out disputes on seemingly peripheral motions and produced flashes of exasperation.

When Cannon initially permitted the defense to file a motion that would include names of government witnesses, prosecutors implored her to reconsider, citing what they said were security risks. When she asked the two sides to formulate jury instructions, prosecutors complained that she had articulated a “fundamentally flawed” premise of the case.

Under her watch, long-shot defense requests lingered for months, causing delays that led her to indefinitely postpone the trial date. She held a hearing on Trump’s legally questionable claim that he was permitted under the Presidential Records Act to take the files to Mar-a-Lago, and agreed before dismissing the case to revisit a different judge’s order that gave prosecutors access to Corcoran, Trump’s lawyer.

Smith’s team had hoped for a trial that could have started last spring. Instead, prosecutors found themselves before Cannon for a multiday hearing in June over Smith’s appointment, where Harbach lamented that defense lawyers had been permitted to “hijack” the proceedings with what he said were frivolous arguments.

Days later, Trump’s lawyers got an unexpected lift from the Supreme Court immunity ruling, which included a concurring opinion from Justice Clarence Thomas backing their position that Smith’s appointment was illegal.

Just like that, an argument that to many legal experts seemed dubious had an endorsement from a member of the nation’s highest court.

Even as frustrations mounted, department officials never sought Cannon’s removal from the case, a low-probability request that likely would have exacerbated relations had it failed. They did not do so even when they told the Atlanta-based 11th U.S. Circuit Court of Appeals in August that her order dismissing the case relied on a “nonsensical” analysis.

The appeal is pending before that court, which has the option to reassign the case if it reverses Cannon’s ruling.

The Washington delay

Late last year, the judge overseeing Trump’s election interference case was pushing toward trial.

With an eye toward a March 2024 date, U.S. District Judge Tanya Chutkan planned to summon District of Columbia residents to complete a questionnaire in a step toward winnowing the potential juror pool. Officials braced for a crush of reporters covering the historic trial.

It screeched to a halt in December.

From the start, allegations that Trump broke the law through actions he took in the White House seemed destined for a protracted court fight testing the limits of presidential power. So it was hardly surprising when Trump’s lawyers demanded the case’s dismissal, arguing he enjoyed absolute immunity from prosecution.

Chutkan, who was nominated by Democratic President Barack Obama, rejected the argument with a December ruling that said the office of the president “does not confer a lifelong ‘get-out-of-jail-free’ pass.”

But crucially, she put the case on hold to give Trump time to appeal to Washington’s federal appeals court and ultimately the Supreme Court.

It would be nearly a year from the time the case was frozen before it was back in Chutkan’s courtroom. By then, the indictment was slimmed down, and it wasn’t clear when — if ever — there would be a trial.

The investigation into the attack on the Capitol on Jan. 6, 2021 — which has become the largest in Justice Department history — had consumed agents and prosecutors by the time Garland was sworn in as attorney general two months later.

Prosecutors had begun charging rioters through a bottom-up investigative strategy heavily focused on the most violent offenders who attacked police and far-right militia group members who were suspected of planning and coordination. Another investigative effort searching for financial ties between the rioters and Trump allies ultimately hit a dead end.

One year into the investigation, Garland defended the department’s deliberate pace as pressure mounted for the Justice Department to hold accountable more than just those who stormed the seat of American democracy.

“The Justice Department remains committed to holding all January 6th perpetrators, at any level, accountable under law — whether they were present that day or were otherwise criminally responsible for the assault on our democracy,” Garland said at the time. “We will follow the facts wherever they lead.”

The facts led squarely to Trump, according to a conspiracy and obstruction indictment filed nearly nine months after Smith’s appointment. Trump, for his part, has repeatedly maintained that he was entitled to challenge an election that he still insists was stolen even though judges and his own attorney general concluded otherwise.

The Trump team’s pursuit of immunity claims, which Chutkan swatted away without a hearing, snarled the case before it could ever develop.

Without ever explicitly mentioning the 2024 election, Smith’s team in December asked the Supreme Court to leapfrog Washington’s federal appeals court and rule quickly on whether Trump could be prosecuted. Acknowledging the “extraordinary request,” Smith’s team called it “an extraordinary case.” Trump’s campaign accused Smith of trying to rush to trial for political purposes.

After the Supreme Court denied Smith’s request to immediately take up the case, the federal appeals court heard arguments and joined Chutkan in turning aside the immunity claims. It would be another two months before the Supreme Court, in late April, said it was prepared to consider the case.

During arguments , several conservative justices indicated they were prepared to limit when former presidents might be prosecuted.

“This case has huge implications for the presidency, for the future of the presidency, for the future of the country,” said Justice Brett Kavanaugh. The court, added Justice Neil Gorsuch, is writing a decision “for the ages.” Both were nominated by Trump.

The Supreme Court moved quickly in prior cases involving presidents, deciding the 1974 Watergate tapes case against Republican President Richard Nixon just 16 days after arguments. In Trump’s case, the justices issued their ruling on July 1, the last day of their term and more than nine weeks after having heard arguments.

The decision held that Trump was absolutely immune from prosecution for acts involving core constitutional functions — in the process, stripping from the indictment Trump’s dealings with the Justice Department — and at least presumptively immune for other official actions. The court also reaffirmed that no immunity exists for a president’s private acts, like those taken as a candidate.

But the justices didn’t spell out which allegations Trump could be prosecuted for, leaving it to Chutkan to decide. Smith subsequently filed a new indictment removing references to allegations that prosecutors believed could be considered official acts.

Among the acts in legal limbo is Trump’s badgering of his vice president, Mike Pence, to refuse to certify the electoral results. Pence, who had declined to testify before Congress, became an important witness for Smith’s team after prosecutors secured court approval to enforce a subpoena for his grand jury testimony. It was a key courtroom victory given his proximity to the then-president and the fact that Pence took contemporaneous notes of conversations with Trump.

With prosecutors and Trump’s lawyers back in her courtroom for the first time this year, Chutkan vowed in September that the election would not affect how she proceeded. She acknowledged that whatever she decided would be appealed again, likely to the Supreme Court.

That means a trial, if it happens at all, could be a year or more away.

“There’s no rush to judgment here,” Chutkan said.

The path forward

The classified documents case remains frozen unless an appeals court resurrects it.

That’s in contrast to the election interference case, where, in an effort to persuade Chutkan that the case should proceed, prosecutors submitted a 165-page brief featuring revelations about the alleged conspiracy.

In one example, the filing unsealed this month quotes Trump as saying “the details don’t matter” when he was told that bogus election fraud claims would not stand up in court. And it says he responded with “So what?” when informed that Pence was in potential peril at the Capitol on Jan. 6.

No matter what happens, the cases’ topsy-turvy trajectory provides further proof that accountability for a president — whether through an impeachment process or criminal case — is never guaranteed, said Princeton University presidential historian Julian Zelizer.

The public is “counting on elected presidents to follow certain legal guardrails.” But, he added, “holding them accountable is not very easy at all.”