Why Jack Smith Is in 'Lose Lose' Battle With Aileen Cannon

Special counsel Jack Smith is in a "lose lose" battle with the judge in Donald Trump's classified documents case, according to a former federal prosecutor.

Neama Rahmani told Newsweek that the more Smith challenges U.S. District Judge Aileen Cannon's rulings to a higher court, the easier it will be for Trump to delay the case past the 2024 presidential election.

Rahmani said Trump could then kill the case completely if he was elected to a second White House term.

Cannon, a Trump appointee, is overseeing the case, in which the former president is accused of illegally retaining classified documents, hoarding them at his Mar-a-Lago resort in Florida and obstructing attempts by federal officials to retrieve them. The former president, and presumptive Republican candidate in the 2024 presidential election, has pleaded not guilty to the charges against him. He has denied any wrongdoing in the case and has said the documents he retained were personal.

jack smith
Special counsel Jack Smith addresses members of the media at the US Department of Justice building in Washington, DC, on August 1, 2023. Smith has been sparring with the judge in Donald Trump's classified documents... Saul Loeb/Getty Images

Newsweek sought email comment from Trump's attorney and from Smith's office on Wednesday.

Rahmani made his comments after a series of tense legal briefs by Smith and Cannon where they both accused each other of acting unreasonably.

Smith warned Cannon in an April 2 filing that he would appeal to a higher court if she did not change the wording of her controversial proposed jury instruction.

In a written response on April 4, Cannon called Smith's warning "unprecedented and unjust."

Cannon's asked attorneys in the case to provide two proposed instructions, including one that suggest the jury is permitted to consider that Trump had a legal right to keep presidential records as personal items.

"Judge Cannon is wrong on the law, but Smith is in a lose-lose situation," Rahmani said. "If Cannon issues another erroneous ruling, this time on jury instructions, Smith will have to appeal to the Eleventh Circuit and delay the case even further when we don't even have a trial date."

"Delay is Trump's best defense because if he wins in November, he can't be prosecuted," Rahmani added.

If elected president, Trump has a number of options including pardoning himself or appointing a favorable attorney general to kill the case.

Smith has warned Cannon that the jury instruction issue must be resolved before trial. That's because Cannon, a Trump appointee, could decide that Trump had a legal right to hold the documents and acquit Trump before the case goes to jury deliberation.

Smith's brief warns that that would be unfair as, after a jury is sworn in, the double jeopardy rule would apply and Trump could not be tried again for the same alleged crimes. Alternatively, the jury could acquit Trump based on Cannon's jury instruction that Trump had a legal right to hold the documents as personal possessions.

"If Judge Cannon doesn't rule and kicks the proverbial can down the road, Smith will be forced to take an appeal or an extraordinary writ right before or in the middle of trial," Rahmani said.

Rahmani, now the president of the West Coast Trial Lawyers law firm, said that Smith will have to get the issue resolved before trial.

"If he is unable to do so and the jury returns a not guilty verdict based on incorrect jury instructions, Smith won't be able to appeal an acquittal because jeopardy has attached," he said.

Uncommon Knowledge

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Newsweek is committed to challenging conventional wisdom and finding connections in the search for common ground.

About the writer


Sean O'Driscoll is a Newsweek Senior Crime and Courts Reporter based in Ireland. His focus is reporting on U.S. law. ... Read more

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