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Documents case against Trump appears strong, but prosecutors still face hurdles, legal experts say

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A photo provided by the Justice Department, and included in the unsealed indictment of former president Donald Trump, showed 80 or more document boxes in a storage room at Mar-a-Lago.DEPARTMENT OF JUSTICE/NYT

WASHINGTON — The classified documents case against Donald Trump unveiled Friday is full of seemingly damning evidence but is by no means a slam dunk for the Justice Department as it prepares for an unprecedented prosecution of a former president, legal experts said Friday.

The 37-count indictment against Trump unsealed in Miami laid out in detail allegations that he illegally took dozens of classified documents to his Florida home and then conspired to keep them from federal officials.

“It is an extremely damning indictment,” Jonathan Turley, a George Washington University law professor who testified in Trump’s favor in both of his impeachments, told Fox News. “The Trump team should not fool themselves. These are hits below the water line.”


But even as some of Trump’s opponents reveled in the indictment — “GUILTY AS SIN,” tweeted Representative Steve Cohen, a Tennessee Democrat — there are several challenges for prosecutors in obtaining a conviction.

The assignment of a Trump-appointed judge to handle the case, at least initially, poses a potential obstacle for the Justice Department, as does the jury pool in Florida, a state that Trump won in his two previous presidential campaigns. Trump has the resources and motivation to file motions that could push a trial past the 2024 election, in which he’s hoping to win a return to the White House.

And Trump’s ability to speak unconstrained about the case in the meantime with the megaphone his celebrity provides is another hurdle for government lawyers, who are limited by rules and procedures as to what they can say publicly.

“It’s going to be a long, difficult haul between now and calling the first witness in the case,” said Jimmy Gurulé, a law professor at the University of Notre Dame who teaches national security law. “There are a lot of unknowns because we’re in uncharted waters.”


One of those is when the case would get to trial. It’s a complicated case involving classified documents with potential national security implications. The judicial system favors the defendant, so Trump’s lawyers will have the ability to file motions to delay the case as much as possible if they want.

Trump is already slated for trial in New York in March following his indictment on state charges that he illegally concealed hush money payments during the 2016 presidential campaign to squelch claims of an extramarital affair.

Renato Mariotti, a partner at the law firm Bryan Cave Leighton Paisner in Chicago who is a former federal prosecutor, said he doesn’t anticipate a trial until after the 2024 election.

“The only way this would happen before the election is if Trump and the judge both wanted that to happen and took significant steps to make that happen,” Mariotti said. “I don’t see what his incentive would be to do that. Even then, I think it would be a very significant challenge given the breadth of the classified information, which creates a lot of unique circumstances.”

Trump shows no sign he wants to expedite the process, especially since he could order the Justice Department to drop the case if he returns to the White House in January 2025.

“I’m an innocent man,” Trump said on a video he released Thursday night, after announcing his indictment on Truth Social. “I did nothing wrong and we will fight this just like we’ve been fighting for seven years.”


Harvard Law professor Laurence Tribe even speculated Friday that Trump could try to move the trial to Washington, D.C., as a stalling tactic.

“Don’t be surprised if Trump files a challenge to venue in Florida — where he of course prefers to be tried — just to use up time with a futile claim that the crime, if any, really occurred in DC when he first took the top secret papers from the White House,” Tribe wrote on Twitter, comparing him to a trickster from folklore. “Just like Brer Rabbit!”

The case had appeared to be headed for trial in Washington, where the special counsel, Jack Smith, had been presenting evidence to a grand jury. But a grand jury recently was convened in Miami and it handed up the indictment. The Justice Department’s shift to Florida was believed to be designed in part to avoid a venue challenge from Trump’s legal team.

In addition to Florida having a more favorable pool of jurors for Trump, the judge assigned to the case in the Southern District of Florida could also be a potential advantage to the former president. Judge Aileen Cannon was nominated by Trump in 2020, and she issued a ruling in his favor over the FBI seizure of records from his Mar-a-Lago home last year. The US 11th Circuit Court of Appeals reversed her ruling.

“In that prior decision, the judge really went far out of her way to find in Trump’s favor and the 11th Circuit said, ‘No, stop, you can’t do that,’ “ said Sarah Krissoff, a partner at the Day Pitney law firm in New York and a former assistant US attorney. “I think she in particular may be a challenge for the prosecution. ... She may be out of the box skeptical of the government case and really put the government to the test on the case.”


Trump’s experience in fighting multiple legal cases in the past and his large financial resources will be another obstacle for the Justice Department. He has numerous ways to get his message out through free media, campaign rallies, and paid ads to frame a narrative that he’s being treated unfairly in the court of public opinion.

Of course, that effort began well before the indictment. For months, Trump has sought to muddy the waters of his classified document troubles by saying that President Biden had even more documents found at his home. In January, White House lawyers notified the Justice Department that they had discovered a small number of classified records stored in Biden’s Delaware home and an office he used at a Washington think tank before he became president. Attorney General Merrick Garland appointed a special counsel to investigate and that probe is ongoing.

Krissoff said it was a false comparison.

“There’s a long history of people having documents they shouldn’t have on both sides of the aisle in all aspects of government,” she said. “This case really isn’t about that. It’s about what happens after those documents were identified and requests were made to get those documents back.”


But unlike most criminal defendants, Trump has the ability to disseminate his message about the case while at the same time stalling the trial that would allow the government to counter it in court, Krissoff said.

“It will make it much more difficult for the prosecution because every challenge that could be brought is going to be brought,” she said. “Even if those challenges don’t have merit, they can fight every fight. They’re going to make it as hard as possible.”

Jim Puzzanghera can be reached at Follow him @JimPuzzanghera.