The one-time national security adviser is among several senior officials who have been investigated for improperly storing or sharing the government’s secrets.
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How John Bolton’s criminal case stacks up to other high-profile classified docs probes
The one-time national security adviser is among several senior officials who have been investigated for improperly storing or sharing the government’s secrets.
This courtroom sketch depicts former Trump administration national security adviser John Bolton being sworn-in.
A courtroom sketch depicts former Trump administration national security adviser John Bolton’s swearing-in during his arraignment Oct. 17, 2025. | Dana Verkouteren/AP
By Josh Gerstein
10/22/2025 05:55 AM EDT
John Bolton is in good — or at least prominent — company.
In facing an investigation and, now, prosecution for allegedly mishandling classified information, Bolton joins a long list of high-ranking officials who have confronted allegations they were cavalier, or worse, with secrets entrusted to them as they oversaw some of the U.S. government’s most sensitive military, intelligence and diplomatic endeavors.
Bolton’s predicament echoes inquiries that resulted in criminal cases against President Donald Trump, former CIA Directors David Petraeus and John Deutch, and former national security adviser Sandy Berger.
And it resurfaces persistent questions about fairness in the handling of similar probes that haven’t produced criminal charges, including investigations into former President Joe Biden, former Secretary of State Hillary Clinton and several members of Trump’s Cabinet.
Bolton’s case comes as Trump’s Justice Department secured felony charges against former FBI Director James Comey and New York Attorney General Letitia James with relatively flimsy indictments from a Trump-picked, first-time prosecutor. While the cases have been panned by critics as political maneuvers against the president’s foes, the Bolton case, propped up by an 18-page indictment brought by career prosecutors, appears substantial.
Prosecutors have historically made charging decisions in classified information cases by doing a detailed comparison against past prosecutions, as well as those where the officials escaped criminal charges — making the cases that came before Bolton newly relevant.
The similarities and differences are also certain to feature prominently in expected motions from Bolton’s defense to have the case against him tossed out on grounds of vindictive and selective prosecution. Bolton served as Trump’s national security adviser during his first term, but the men became adversaries, with Bolton emerging as one of Trump’s most prominent critics on the right and Trump calling for Bolton to be jailed.
Here’s POLITICO’s look at some of the most prominent prosecutions and investigations that provide the backdrop to the Bolton case:
President Donald Trump
What happened: Trump accumulated hundreds of classified documents at Mar-a-Lago during his presidency and the tumultuous transition of power to Biden in 2021. Officials repeatedly demanded those documents and other unclassified files back. Trump aides returned 15 boxes in January 2022. Prosecutors acquired another 38 classified documents in June 2022 in response to a grand jury subpoena, but were convinced more remained. A court-ordered FBI search in August 2022 turned up more than 100 additional classified records, including 17 “top secret” documents.
Attorney General Merrick Garland appointed special counsel Jack Smith to investigate. In June 2023, Trump was indicted on 31 counts of willful retention of national defense information, along with six other counts stemming from alleged efforts to cover up the presence of the sensitive documents. One additional retention charge was added the following month, along with two more obstruction charges.
Outcome: U.S. District Judge Aileen Cannon, a Trump appointee, dismissed the criminal prosecution in July 2024 on the grounds that Smith’s appointment was unconstitutional. Smith appealed, but after Trump won the 2024 presidential election, the Justice Department dropped the appeal, citing a long-standing policy against criminal prosecution of a sitting president.
Similarities to Bolton’s case: Prosecutors contend that the former national security adviser had numerous warnings that he had classified information in his possession, just as Trump did. The alleged secrets also span a wide range of topics over an extended period of time and implicate sensitive White House deliberations.
Differences with Bolton’s case: While the FBI reported finding documents marked classified at Bolton’s Washington office, the indictment returned last week charges Bolton only with sharing and possessing his own notes rather than marked documents. Bolton also does not face the obstruction and false-statement charges Trump did. The case against Bolton could be simpler for prosecutors to prove because it doesn’t raise unique legal issues stemming from a sitting president’s power to declassify virtually any government secrets.
Signalgate
What happened: In March, several senior Trump administration officials used a group chat on the messaging app Signal to discuss details of planned military strikes in Yemen. The officials included then-national security adviser Mike Waltz, Defense Secretary Pete Hegseth, Vice President JD Vance, Secretary of State Marco Rubio and others. Waltz or an associate appeared to have accidentally added a journalist, Atlantic Editor Jeffrey Goldberg, to the group. Hegseth also reportedly included his wife, brother and attorney in another Signal chat about U.S. military operations in Yemen.
Outcome: The Trump administration moved to limit the fallout from the Signal chats by claiming no classified information was discussed, but Goldberg and other longtime military experts rejected that assertion. The Defense Department’s Inspector General launched an investigation, but Attorney General Pam Bondi suggested there was no need for the Justice Department to look into the matter.
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Sen. Rand Paul and Katelyn Jetelina | The Conversation
“It was sensitive information, not classified, and inadvertently released,” Bondi said, before praising the efficacy of the strikes. “What we should be talking about is it was a very successful mission.”
Since then, there has been no outward sign that the Justice Department is exploring whether the Signal chats violated the law or merit prosecution. In theory, participants in the chats could face discipline, but that seems unlikely.
“If it’s normal course, there would have been an investigation opened on that. I don’t know if it gets charged, but it gets run to ground,” said one former senior DOJ official, who was granted anonymity to avoid potential retaliation. “Because they didn’t bother to do that, all the departures from normal process make the Bolton case seem suspect.”
Similarities to Bolton’s case: Signalgate involved potentially classified information rather than marked documents. Both episodes involve platforms not authorized for classified communications, with Bolton using two personal email accounts as well as a commercial messaging app that offered encryption. Hegseth’s Signal chat with his family seems a close parallel to Bolton’s emails to relatives.
Differences with Bolton’s case: Bolton’s notes, which prosecutors called “diary-like entries,” spanned a variety of subjects from an adversary’s missile launch plans to U.S.-run covert actions and covered nearly all his year-and-a-half-long tenure as national security adviser. The main Signal chat about Yemen covered only five days and focused on that distinct topic. It’s not clear how often top Trump officials had similar chats on other sensitive or classified subjects.
President Joe Biden
What happened: In late 2022, classified documents were found at the Washington office of a think tank Biden used. In early 2023, more classified documents were found in a garage and an adjoining room at Biden’s Delaware home. The records dated to his service as vice president and to his Senate career. Biden also kept notebooks from his vice presidential years that contained classified information.
Garland appointed special counsel Robert Hur to investigate.
Outcome: Since Biden was a sitting president at the time of the probe, he could not be charged under DOJ policy. Hur said he would not have sought to charge Biden even in the absence of that roadblock. Hur called Biden’s handling of the classified information “totally irresponsible.” The prosecutor found evidence that Biden knew he had classified information stored at a rental home after leaving office, but concluded that various uncertainties would’ve undermined the chance for a successful prosecution, including Biden appearing to be “a sympathetic, well-meaning, elderly man with a poor memory.”
Hur said Biden clearly deliberately retained notebooks containing classified information, but the government’s failure to take action to recover similar notes kept by President Ronald Reagan gave plausibility to Biden’s claim that his notes were his “property,” and he believed he was entitled to keep them.
Similarities to Bolton’s case: Biden’s notebooks are not unlike the diaries Bolton is accused of keeping. Biden also shared those materials with a ghostwriter for a book. The indictment against Bolton contends the lengthy notes he sent to his family were supposed to be the raw material for the book he ultimately published the year after he left the White House.
Differences with Bolton’s case: No evidence was uncovered that any of Biden’s classified materials were compromised by a foreign government. However, Bolton — who has been the focus of efforts by Iran to kill him — told the FBI through a representative in 2021 that he believed his email had been hacked by Iran as well. The indictment says some of the classified information Bolton sent to his family members was sent by email and others through an encrypted app.
Secretary of State Hillary Clinton
What happened: Secretary of State Hillary Clinton used a personal email account and server for her email traffic during her four years as America’s chief diplomat. Clinton’s email use was discovered by congressional investigators probing the Benghazi fiasco. In December 2014, she turned over about 30,000 emails to the State Department.
The FBI investigated and found that 110 messages in Clinton’s account contained classified information, including eight chains with “top secret” information and 36 with “secret.” Comey, the then-FBI director, said it was “extremely careless” for such information to be handled on a private server.
Outcome: No charges were brought, but the controversy dogged Clinton throughout her 2016 presidential campaign. Many experts believe it contributed to her loss. A State Department report released during the first Trump administration found no “systemic” effort by Clinton or her aides to bypass classified information restrictions.
Similarities to Bolton’s case: Bolton’s use of private email accounts to discuss official government business, including sensitive national security and diplomatic matters over a protracted period of time, has some parallels to Clinton’s reliance on a private account. Both cases also include periods of time when the high-profile government officials were communicating while outside the U.S.
Differences with Bolton’s case: There’s little indication Clinton was seeking to use her email for things she knew to be classified, as prosecutors have alleged in Bolton’s case. Clinton was generally on the receiving end of the messages, therefore not deciding what content to include. She may also have relied on the judgment of experienced aides about what was permissible to discuss in an unclassified channel. And while hackers attempted to access Clinton’s email account, there’s no indication they succeeded, as they did with Bolton.
Former national security adviser Sandy Berger
What happened: In 2003, while reviewing highly classified documents at the National Archives in connection with requests from the 9/11 Commission, Berger removed five copies of a “top secret” Clinton White House document about planning for al Qaeda-related threats. Berger stashed four of the copies under a construction trailer near the Archives so he could retrieve them later.
One Archives employee claimed to have seen Berger stuffing a document into his pants or socks, which Berger consistently denied. He returned two of the documents but said he had cut up others, which were not recovered.
The Justice Department, the FBI and the Archives’ Inspector General investigated the episode.
Outcome: In a deal with prosecutors, Berger pleaded guilty in 2005 to one misdemeanor charge of mishandling classified information and agreed to give up his security clearance for at least three years. He got no prison time, but a judge imposed a $50,000 fine, five times what prosecutors sought. Berger died in 2015.
Similarities to Bolton’s case: Berger was serving in the same position as Bolton and had extensive experience dealing with classified information rules.
Differences with Bolton’s case: Berger’s actions could have resulted in national security secrets reaching unauthorized people, but there’s no indication they did. He appeared to have violated the rules as a matter of personal convenience to get his work done. However, the brazenness of sneaking physical documents out of the Archives and the subterfuge involved in stashing and leaving them unattended made the case particularly egregious.
Former CIA Director David Petraeus
What happened: While serving as CIA director, Gen. David Petraeus kept notebooks at his home containing highly classified “code word” information about military operations he oversaw in Afghanistan. Petraeus also shared the information with an Army reservist who was writing his biography and with whom he was having an affair. She had a security clearance but no official approval to see the secrets in question.
When the FBI interviewed Petraeus in October 2012, he denied having given any classified information to the biographer.
Outcome: Soon after that interview, Petraeus resigned from the CIA, citing poor judgment related to the extramarital affair. In March 2015, Petraeus agreed to plead guilty to a single misdemeanor count of mishandling classified information. He was sentenced to 2 years probation and a $100,000 fine. FBI agents and some prosecutors objected to the plea deal, warning that it would be used by lower-level officials seeking leniency for similar conduct.
Similarities to Bolton’s case: Petraeus also retained diary-like material which the government contends was highly classified. He also shared it with a close associate in the course of preparations for a book project.
Differences with Bolton’s case: The extramarital affair adds a twist of blackmail vulnerability to Petraeus’ case. Prosecutors also had an audio recording of Petraeus saying he knew there was “code word” classified information in his notebooks. However, there’s no indication the classified information was disclosed to hackers or a hostile government.
Former CIA Director John Deutch
What happened: During a year and a half as CIA director in the 1990s, Deutch “continuously” accessed classified information on government-issued computers approved only for use of unclassified information at his two homes, according to a CIA Inspector General report. Some of the information was “top secret,” involving communications intelligence and covert action.
Outcome: Deutch agreed with federal prosecutors to plead guilty to a misdemeanor and signed a plea agreement in 2001. However, on President Bill Clinton’s last day in office and before the plea paperwork was filed with the court, Clinton pardoned Deutch.
Similarities to Bolton’s case: Some of the highly classified information was contained in 26 volumes of “journals … of daily activities maintained by Deutch while he served at the DoD and CIA.” Deutch’s mishandling of classified information was discovered through his requests for assistance in maintaining his government computers after he stepped down.
Differences with Bolton’s case: While investigators found Deutch’s handling of the classified data made it vulnerable to hacking, they found “no clear evidence” that anyone unauthorized accessed it.