By ERIC TUCKER and ALANNA DURKIN RICHER Associated Press
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WASHINGTON — The FBI investigators who searched Harold Martin’s Maryland property in the fall of 2016 found classified documents — including material at the top secret level — strewn about his home, car and storage shed.

Unlike former President Donald Trump, the former National Security Agency contractor didn’t contest the allegations, ultimately pleading guilty in 2019 and admitting his actions were “wrong, illegal and highly questionable.” But his expressions of contrition and guilty plea to a single count of willful retention of national defense information didn’t spare him the harsh punishment of nine years in prison.

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The resolution of that case looms as an ominous guidepost for the legal jeopardy Trump could face as he confronts 37 felony counts — 31 under the same century-old Espionage Act statute used to prosecute Martin and other defendants alleged to have illegally retained classified documents. Even many like Martin who have pleaded guilty and accepted responsibility have nonetheless been socked with yearslong prison sentences.

“When they decide to pursue a willful mishandling case, it’s to send a message: that we take these cases very seriously,” said Michael Zweiback, a defense lawyer and former Justice Department prosecutor. “They almost always are seeking jail time.”

How much prison time the former president could face in the event of a conviction is impossible to say, with such a decision ultimately up to the trial judge — in this case, a Trump appointee who has already demonstrated a willingness to rule in his favor. It’s also hard to know the extent to which other factors — including the logistical and political complications of jailing a former president — might play a role.

The Espionage Act offense is punishable by up to 10 years in prison, though it’s rare for first-time federal offenders to get close to the maximum. But beyond the retention, prosecutors have also identified multiple aggravating factors in Trump’s alleged conduct, accusing him of seeking to enlist others — including a lawyer and aides — to hide the records from investigators and showing off some to visitors. Some of the other counts in the indictment, including conspiracy to obstruct justice, call for up to 20 years in prison.

Justice Department prosecutors in recent years have used the Espionage Act provision against a variety of defendants, including a West Virginia woman who retained an NSA document related to a foreign government’s military and political issues. Elizabeth Jo Shirley pleaded guilty in 2020 to a willful retention count and was sentenced to eight years in prison.

This month, a retired Air Force intelligence officer named Robert Birchum was sentenced to three years in prison after pleading guilty to keeping classified files at his home, his overseas officer’s quarters and a storage pod in his driveway.

Many defendants have pleaded guilty, rather than face trial, though not all have gone to prison. Trump — who also faces charges related to hush-money payments in New York state court — has shown no signs that he could be headed toward a plea deal, vigorously insisting he is innocent and personally attacking Justice Department special counsel Jack Smith hours after appearing in Miami federal court Tuesday.

Despite the details in the indictment, Trump does have some avenues to try to contest the charges.

For one thing, he’s drawn Judge Aileen Cannon, who sided with Trump last year in the former president’s bid to appoint a special master to conduct an independent review of the seized classified documents. Citing the “stigma” she said was associated with an FBI search of Trump’s home, she said a “future indictment” based on items that should’ve been returned to Trump “would result in reputational harm of a decidedly different order of magnitude.”

A three-judge panel of the U.S. Court of Appeals for the 11th Circuit unanimously overturned her ruling, which was widely criticized by legal experts as extraordinary and unusually broad.