‘Rife with political risks’: Why Garland faces tough calls in considering Trump charges

Trump’s stature as a former president, his likely 2024 run and the challenges of picking an unbiased jury while using classified records make a potential indictment singularly difficult.

Donald Trump leaves Trump Tower in New York City on Aug. 10 to meet with New York Attorney General Letitia James in connection with her civil investigation.James Devaney / GC Images/Getty Images file

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Sept. 8, 2022, 6:27 AM MST

By Marc Caputo and Ryan J. Reilly

Over the past 16 months, the federal government sent letters and emails, made phone calls, issued a criminal subpoena and finally executed a search warrant to retrieve a bewildering number of sensitive government records from former President Donald Trump’s Mar-a-Lago home and club in Palm Beach, Florida.

Listed in two Justice Department court filings filed in as many weeks, the paper trail of records lay out a road map for what could be the first criminal indictment of a former president, according to legal experts and former Justice Department officials who spoke to NBC News and say Attorney General Merrick Garland probably has enough evidence now to charge Trump with mishandling national defense information and obstruction of justice.

But it’s a singularly complicated task, wrought with myriad difficulties — chiefly the explosive political proposition of indicting a former president — that no attorney general has faced before, according to Garland’s predecessors, former prosecutors and seasoned federal defense attorneys.

“The attorney general is not in a monastery, unconnected to the world that surrounds him,” former Attorney General Eric Holder, who was appointed by President Barack Obama, said in an interview, discussing the complications of the case. “And yet, your primary responsibility is to enforce the law.”

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Garland has repeatedly emphasized that his decisions are driven by the “facts and the law.” And Holder, other former prosecutors and one of his Republican predecessors as attorney general say they trust him. But in weighing whether to charge a political figure, Holder acknowledged that “some part of the calculus is the impact of any prosecution decision” on the country.

Under federal guidelines, prosecutors aren’t supposed to charge if they don’t believe there’s enough evidence to ensure the probability of sustaining a conviction, a difficult consideration in any case, because they need to impanel 12 impartial jurors to unanimously agree on a verdict. The problem is magnified to historic proportions by a polarizing figure like Trump as he positions himself for a possible rematch against President Joe Biden, who appointed Garland. 

Trump’s status as a former president played in his favor Monday, when a federal judge he appointed in the Southern District of Florida, Aileen Cannon, shocked legal experts by temporarily halting some aspects of the criminal investigation to allow a yet-to-be-appointed third-party “special master” review of all the documents and records seized from Mar-a-Lago in the Aug. 8 search. 

Cannon’s ruling gave a measure of credence to Trump’s argument, hotly disputed by the Justice Department and legal experts across the political spectrum, that a former president could assert executive privilege claims over records the government argues weren’t his to possess. 

“The Court takes into account the undeniably unprecedented nature of the search of a former President’s residence,” Cannon wrote, emphasizing that with Trump’s “former position as President of the United States, the stigma associated with the subject seizure is in a league of its own.”

Many legal experts roundly criticized the ruling, particularly the unprecedented decision that a special master should be authorized to wade into thorny issues of executive privilege. But it was hailed publicly and privately by Trump, his advisers and confidants, four of whom spoke to NBC News on condition of anonymity to freely describe conversations with, and the state of mind of, the former president.

“What you saw with Cannon you’re going to see over and over again, and I’m not sure Justice knows what it’s getting into,” said a confidant who spoke with Trump about the case. “This is a case about presidential records and executive powers. It’s got ‘Supreme Court’ written all over it. He’s going to go all out. And if it ever gets to trial, he’ll win. It takes just on