Hillary Clinton initially brushed off critics of her decision to use a private email server by saying it was more convenient. But now her “convenience” is derailing her presidential campaign. Yesterday, the former Secretary of State and current Democratic frontrunner agreed to turn over her personal server to the Department of Justice.

Exactly how much her insistence on opaque, private control over digital communications will mangle her chances is still in question. Federal investigators are trying to figure out if classified information was mishandled on her server, and a probe from the Intelligence Community Inspector General found that at least four of the emails on the server contained information that remains classified.

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“I’m confident that I never sent nor received any information that was classified at the time it was sent or received,” Clinton has insisted, couching her denial in language that gives her wiggle room to later admit that her “confidence” was unwarranted. State Department spokesman John Kirby has used similarly strategic language defending Clinton, emphasizing that the alleged classified emails were not “marked classified.” Kirby’s defensive posture implies that if what Clinton’s servers hold isn’t explicitly earmarked as Confidential/Secret/Top Secret, it’s no harm, no foul.

If this calculated deflection sounds familiar, it’s because Clinton is far from the first high-powered political player accused of mishandling classified information, and far from the first to initially deny it.

Here’s a list of people the Clinton team may want to call up for legal advice:

1. Alberto Gonzalez

What he mishandled: Classified documents and handwritten notes on classified documents

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How he mishandled them: Swung them around in his briefcase

Former Attorney General Alberto Gonzalez took notes on the government’s warrantless wiretapping program and how it interrogates terrorism detainees and got caught carrying them around in his briefcase. The scrawled notes, like Clinton’s emails, were not explicitly marked as classified. He also kept classified documents in a safe in his office that wasn’t properly secured. In 2008, the inspector general published a report outlining Gonzalez’s loose security habits.

What happened to him: For treating classified information like a hot salami sandwich, Gonzalez got...admonished. He was never charged with a crime.

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2. Sandy Berger

What he mishandled: Classified documents and his own handwritten notes on classified documents, about the Clinton Administration’s terrorism record

How he mishandled them: Stole and destroyed with pair of scissors

Former National Security Adviser Sandy Berger had no intentions of leaking documents—in fact, he got in trouble for destroying them.

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In 2003, Berger took classified documents from the National Archives and Records Administration. He took five documents, but once he realized many were identical, he cut the ones he considered duplicates up with scissors at his office. He also took his own handwritten notes, which, like Clinton’s emails, were not specifically marked as classified. Nonetheless, prosecutors noted that he was forbidden to remove them from the Archives “until a classification review was done.”

What happened to him: After initially attempting to suggest that—whoopsie!—he’d flaked out and moseyed off with the documents, Berger fessed up, pled guilty to a misdemeanor, and was sentenced to 100 hours of community service and a $50,000 fine.

3. John Deutch

What he mishandled: 17,000 classified documents (contents unknown)

How he mishandled it: Generally inept computer security and/or lack of fucks given about computer security*

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Former CIA director John Deutch was caught keeping classified government information on his home computers in Maryland and Massachusetts. In 1996, he left the CIA after his sloppy methods came to light and an investigation followed. Sen. Chuck Grassley (R-Iowa)—now chirping Clinton for her email scandal—was outspoken against Deutch, calling him “a congenital downloader of classified information.’’

What happened to him: He lost security clearances, but he was never charged with a crime.

On the last day of his presidency, Bill Clinton pardoned Deutch.

*sound familiar?

4. David Petraeus

What he mishandled: Notes on classified meetings; classified documents; security codes; names of covert operatives; war strategy; his marriage

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How he mishandled it: In a lusty stupor

The only mishandler of classified information on this list to do it all for the nookie, former CIA Director David Petraeus watched his career disintegrate after he was caught for giving eight notebooks full of classified materials to his biographer-cum-sex partner. The notebooks contained extensive notes Petraeus took during meetings, notes that revealed top secret code information and details about war strategy.

After initially denying that he gave his mistress the notebooks, Petraeus pled guilty to one count of unauthorized removal and retention of classified material.

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What happened to him: The rich, powerful, philandering fallen military superstar got off easy for his misdeeds in 2015, sentenced to two years’ probation and fined $100,000 for storing gobs of classified information in a rucksack at his mistress’ house.

5. Leon Panetta

What he mishandled: Classified information on the raid of Osama bin Laden

How he mishandled it: By running his mouth like a schmuck

With three on this list, it’s clear that former CIA directors are shockingly inept at not exposing classified information. Leon Panetta straight-up told classified information to a writer in person, leaking the name of the Navy SEAL credited with killing Osama bin Laden during a speech that was classified as “Top Secret” despite the fact that a Zero Dark Thirty screenwriter without security clearance was in attendance.

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What happened to him: Panetta was not charged despite clearly (albeit dumbly and accidentally) violating the Espionage Act.

6. Jeffrey Sterling

What he mishandled: Hard to say

How he mishandled them: Allegedly

While Clinton’s no whistleblower, her situation may end up having parallels to Former CIA agent Jeffrey Sterling.

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Sterling, who allegedly shared classified information with a New York Times reporter in the early 2000s, was pilloried entirely on circumstantial evidence. He was never caught leaking or mishandling classified documents. Prosecutors argued that records of phone calls and emails between Sterling and the reporter showed that they had talked; they did not show evidence of Sterling discussing classified information.

As Clinton’s investigation continues, her political opponents may use the successful prosecution of Sterling as a way to go after her, even without hard evidence that she stored emails containing classified information.

Clinton is also leaning heavily on the idea that her emails were not classified at the time—leaving room for possibility that information in them could’ve been retroactively classified later. But as lawyer Jesselyn Radack noted today, “retroactively classified information figured prominently in convicting Sterling.” Sterling’s case shows a gaping hole in Clinton’s defense.

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What happened to him: In May 2015, Sterling was sentenced to three and a half years in prison.

Whistleblowers like Sterling, Edward Snowden, and Chelsea Manning have seen their lives shredded after sharing classified documents with reporters, but leakers aren’t the only people who can get busted for doing bad things with top secret intel. We’ll never hear about most of the people who bungle classified information. “Most often, it’s not prosecuted,” Bradley Moss, an attorney who specializes in national security cases, told me. “I handle cases where people mishandle classified information all the time. They just never get prosecuted, they’ll have a security clearance ramification.”

That said, if a classified information fumble is scandalous, egregious, or politically polarizing enough, it’ll come out (and, often, wind up in court). Clinton’s political enemies are frothing at the mouth, with House Select Committee on Benghazi Chairman Trey Gowdy (R-SC) insisting that Clinton has endangered national security. Despite a New York Times report to the contrary, Clinton is not facing a criminal inquiry.

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However, mishandling classified information can carry heavy legal consequences, and just because she isn’t facing one yet doesn’t mean she won’t. And just because information she circulated wasn’t explicitly marked as classified doesn’t mean it wasn’t classified.

Image: AP Photo/J. Scott Applewhite