John Bolton is expected to plead guilty to a single count of retaining classified information as part of a plea deal with the Justice Department, which charged him in October 2025 with 18 counts of mishandling sensitive information.
According to the charges, the former National Security Advisor shared diary notes from his time in the first Trump Administration with his wife and daughter in preparation for his memoir, “The Room Where it Happened.”
The Trump administration filed a 2020 lawsuit against Bolton to prevent the publication of the book, which was highly critical of Trump’s first term. According to one description, Bolton “shows a President addicted to chaos, who embraced our enemies and spurned our friends, and was deeply suspicious of his own government.” Despite accusations the book contained classified information and breached a non-disclosure contract, charges never came, and the book was published in June 2020.
It wasn’t until his second term that Trump was able to indict and force a plea. It did not matter that the book, which was about using executive power to exact revenge, had been on the shelves for six years.
Given the seriousness of the charges, Bolton nonetheless appears to be skirting a more serious punishment. According to the Associated Press, he faces a $2.25 million fine (certainly not peanuts) but is likely to avoid any jail time.
This affair is reminiscent of when former CIA director and four-star General David Petraeus was sentenced in 2015 to two years probation and fined $100,000 for sharing notebooks containing highly classified material with his then-mistress Paula Broadwell. Reports surfaced later that the FBI believed Petraeus shared classified information with journalists, too.
Petraeus would later apologize to Congress. But he kept his four stars and generous pension compliments of the American taxpayer. He is now a consultant and a highly sought-after speaker on geopolitical and military affairs.
But like Bolton, Petraeus remains a member in good standing of the national security state. No doubt Bolton will continue getting invitations to pontificate on CNN, MSNBC or any of the major media on the Iran war, which he supported fulsomely. Both he and Petraeus are two members of the bipartisan War Party in good standing, the former being more hawkish than the other but both staying within the bounds of the Washington establishment.
For that, their punishments were light, especially relative to whistleblowers who entered in the real cross hairs of executive power.
Former CIA officer and whistleblower John Kiriakou in 2007 helped expose the agency’s use of waterboarding, sparking a national debate about the U.S. use of torture or what defenders would call “enhanced interrogation tactics.”
In retaliation, the government got him on a charge of sharing the name of an operative with a reporter, but the reporter never even published the information. Kiriakou was convicted and did two years hard time in prison. A decades-long career of government service destroyed.
Kiriakou would later say in 2015, “My case was not about leaking. It was about torture.”
“The CIA never forgave me for going public with the torture program,” Kiriakou insisted. “Washington runs on leaks—whether they’re authorized or unauthorized. The last three CIA directors have not just leaked classified information, but they’ve leaked the names of covert operatives. There was no harm to national security, and there certainly was no criminal intent. And neither was there harm to national security or criminal intent in my case, yet I was prosecuted and they weren’t.”
“That leads me to believe that my case was not about leaking,” he added.
Kiriakou’s real crime was making the national security state look bad.
The same was true of former National Security Agency senior executive Thomas Drake, who over 15 years ago saw what he believed to be an unconstitutional wiretapping of U.S. citizens in the Bush administration after 9/11, so he went to Congress. When nothing happened, he eventually went to the press via an encrypted email.
When his leak was discovered, Drake was indicted under the Espionage Act for five charges and he faced up to 35 years in prison. After a plea deal in which he pled guilty to one charge of exceeding the authorized use of a government computer (the other charges were dropped) he was sentenced to a year of probation and 240 hours of community service.
This was a better outcome for Drake than the hard time Kiriakou, but his security clearance was revoked, he lost his career in government service, and was forced to work at an Apple store to pay the bills.
PBS Frontline later asked him why the federal government went after him so aggressively and Drake replied, “Because they wanted to send a message. They were going to drive the stake of national security right through me and prop me out on the public common and say: ‘This is what happens. Dare speak truth to enough power, we will be able to make an object lesson of you. You don’t want to do what Mr. Drake did.”
Unlike Bolton and Petraeus, Kiriakaou and Drake paid real prices for their similar crimes. Unlike John Kiriakaou and Thomas Drake, who saw it as their duty to show Americans what was happening in their name in secret, John Bolton and David Petraeus seemingly broke the law for their own personal benefits.
Two were narcissistic, the others, patriotic.
The American national security establishment tolerates its own no matter their faults. But for any patriot who might challenge them or, worse, embarrass them, there is no quarter.
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