Jack Smith Faces Challenges in Prosecuting Trump

Bringing historic federal charges against Donald Trump was just the start. The challenge for Justice Department Special Counsel Jack Smith, as he prepares to argue in court that the former President illegally took national defense secrets to his Florida home and willfully defied efforts to get them back, is to make the charges stick.

No matter the merits of the case, the obstacles for Smith, a taciturn career prosecutor with a medieval-looking beard, are considerable. The case was assigned to a federal judge who has already been chided by an upper court for inappropriately favoring Trump in a ruling over documents seized from his Mar-a-Lago Club. Jurors will be selected from a state that Trump won in 2016 and 2020. And then there’s the personal attacks: Trump has already launched a campaign to impugn Smith’s motives, calling him a “Trump hater” and “deranged.”

The clock is ticking. The Southern District of Florida is known for presiding over a “rocket docket” that moves cases quickly. But even the speediest federal criminal trial can drag out, and Trump, who has spent decades stalling legal challenges, could try to push a verdict out past Election Day on Nov. 5, 2024. A lengthy trial in a high profile federal case is exactly what the Justice Department doesn’t want, with the integrity of the U.S. justice system and possibly the outcome of a presidential election, hanging in the balance.

Smith has spent nearly his entire career prosecuting cases. Raised outside Syracuse, New York, he graduated from State University of New York at Oneonta, and shortly after finishing Harvard Law School was hired in the Manhattan district attorney’s office and then the U.S attorney’s office in Brooklyn. He worked his way up in the Justice Department to eventually lead the public integrity unit that brings cases against public officials accused of corruption. In that position, which he held from 2010 to 2015, he oversaw cases against Democratic Senator Robert Menendez of New Jersey, former Republican governor of Virginia Robert McDonnell, and former congressman Rick Renzi of Arizona.

Smith moved to the U.S. attorney’s office in Nashville in 2015 and briefly became the acting U.S. attorney there in 2017 before leaving to work as vice president of litigation at the private Hospital Corporation of America. Wanting to get back to prosecutions, in 2018 Smith took a job charging international war criminals at the Kosovo Specialist Prosecutor’s Office in The Hague, Netherlands. It was from there that Attorney General Merrick Garland brought him back to be special counsel overseeing the investigation into Donald Trump’s alleged refusal to return classified documents from Mar-a-Lago, and a separate case looking at Trump’s efforts to reverse the 2020 election results and encourage his supporters to violently storm the Capitol Building on Jan. 6, 2021.

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Smith kicked off his prosecution with the indictment he filed in federal court in Miami on June 8. The document alleged in plain, fact-based language that Trump had stored some of the country’s most closely held secrets—including information about U.S. nuclear programs, defense vulnerabilities and attack plans—in the Mar-a-Lago Club ballroom, a bathroom and shower, his bedroom, an office and a storage room. The charges highlight Trump’s alleged obstruction of federal officials when they tried to get them back. Smith charged Trump with a total of 37 counts, including 31 separate instances of “willful retention of national defense information”, as well as conspiracy to obstruct justice, and multiple counts related to withholding or concealing documents from a federal investigation, and a charge of making false statements and representations.

Speaking briefly after the charges were unveiled, Smith reminded Americans that Trump is innocent until proven guilty and that the nation’s laws apply to everyone. But when it comes to making a high-profile criminal case, the particularities of the courtroom can make all the difference. Nearly everyone in the country has an opinion about Donald Trump. It only takes one holdout juror to result in a mistrial. While the case is likely to be heard in a south Florida county that went for Biden in 2020, the whole state of Florida went for Trump in 2016 and 2020, and the juror pool in southwest Florida is likely more packed with Trump supporters than if the case had been brought in heavily Democratic Washington, D.C.

Judges have a lot of power to set the terms of jury selection and instructions to the jury, and Trump’s legal team may have caught a break there. The case has been assigned to Aileen M. Cannon, a 42-year-old Trump-appointed judge who was rebuked by a higher court for inappropriately intervening on Trump’s behalf over a Mar-a-Lago search warrant that was part of Smith’s investigation.

Judges also hold a lot of power over setting a trial date and determining how long a trial takes. Time is not on Smith’s side. Smith said in his rare public statement on Friday that he would “seek a speedy trial.” If the public deserves a verdict before the GOP formally selects a presidential nominee at the Republican National Convention in Milwaukee in August 2024, that’s just over 13 months away. Trump’s shown a pattern over decades of dragging out legal challenges against him.

The “number one challenge” on Smith’s mind has to be that the case will be presided over by Cannon “given that she’s shown that she will be partial to him in her prior rulings,” says Renato Mariotti, a former federal prosecutor. Cannon was appointed by Trump to the bench in 2020, and after the FBI searched Mar-a-Lago, Cannon ordered a special master to sift through the documents to decide what should be returned to the government, but was overruled by a higher court.

A district judge like Cannon has “very significant” power at trial, says Mariotti. For example, prosecutors would not be able to appeal if Cannon decided to throw the case out after the jury is empaneled, Mariotti says. Should Trump be convicted, Cannon would determine his sentence. Smith also “has to be concerned about jury selection,” Mariotti says. “Even one juror could potentially prevent a verdict.”

It is very unlikely Trump will go to trial before the 2024 election, says Mariotti. Even a run-of-the-mill federal case often takes a year at trial, and defense attorneys have a number of ways to delay and slow down a trial with motions and appeals. In a case involving national security documents, the process often takes even longer because defense lawyers have to go through background checks to see sensitive documents.

Norm Eisen, an anti-corruption expert at Brookings Institution and the former special counsel to the House Judiciary Committee from 2019 to 2020 during Trump’s first impeachment says that Smith’s case will face a “less favorable jury pool” than if the case had been brought in Washington, D.C. “But I think it’s to the prosecutors credit that they did not play games with venue,” Eisen said.

Eisen, who has called for Cannon to recuse herself from the case because of her prior rulings being overturned, thinks the higher courts will step in if Cannon shows too much bias toward Trump in court proceedings. “I think the judicial system will take care of business if Judge Cannon is as outrageously and lawlessly in favor of Trump as she was in her initial rulings in the dispute over the Mar-a-Lago search warrant aftermath,” Eisen says.

Trump’s defense team will likely try to slow down the trial and make it look like the prosecutors’ case is overly complex and hard to follow. “Trump may try to make this a complicated, intricate, self-justifying confusing case. Smith needs to keep it simple. This is about a President who jeopardized our national security by removing documents that were classified national defense information and extremely dangerous, and when he was caught, he covered it up,” Eisen says.

Then there’s the war of public opinion, Trump’s favorite battlefield. Trump has already begun trying to define Smith in public as “deranged” and a “Trump hater.” Speaking to GOP supporters at the Georgia state Republican Party convention in Columbus, Georgia on Saturday, Trump went on a rambling takedown of Jack Smith. “I watched him yesterday go up and talk. He talked for about two and a half minutes. He was shaking. He was so scared. He didn’t want to be there. Because ultimately, these are cowards. They’re cowards,” Trump said. “And he’s a big Trump hater, openly he’s a Trump hater.”

But Smith is unlikely to be intimidated, Eisen says. “Jack Smith has tried war criminals who have committed mass atrocities. So I don’t think he is going to be daunted by name calling by Trump.”