John Bolton’s relationship with President Donald Trump went from mutual admiration to a high-profile falling out that has continued to reverberate for years and resulted — most recently — in Bolton reportedly set to plead guilty to charges of mishandling classified information.
Bolton, a longtime foreign policy hawk, Iraq War enthusiast, and former United Nations (UN) Ambassador under former President George W. Bush, was a vocal Trump supporter during the 2016 campaign and transition. (RELATED: Donald Trump Called The Iraq War A ‘Disaster.’ His New National Security Adviser Was Its Biggest Cheerleader)
So much so that Bolton was reported to have been interviewed for Secretary of State during the first Trump administration but instead was passed over for Rex Tillerson, according to an Axios report.
In March 2018, Trump named Bolton his third National Security Advisor, replacing H.R. McMaster. Trump praised Bolton’s toughness and experience.
He appeared frequently on Fox News praising Trump’s “America First” instincts while pushing aggressive positions on Iran, North Korea, and China.
Bolton left the administration in September 2019 after a turbulent 17 months as National Security Advisor marked by repeated clashes with President Trump over foreign policy. The split itself became a public feud, with Trump announcing on social media that he had fired Bolton, while Bolton insisted he had resigned.
A longtime foreign policy hawk, Bolton frequently advocated for a tougher approach toward U.S. adversaries and often found himself at odds with Trump’s diplomatic instincts. Their disagreements came to a head over proposed peace talks with the Taliban, with Bolton reportedly mounting a last-minute effort to derail a Camp David meeting and potential agreement with the group, according to a New York Times report.
Although Trump ultimately canceled the talks, the dispute further strained his relationship with Bolton and preceded the national security adviser’s departure from the administration.
Trump announced Bolton’s exit on social media, writing, “I informed John Bolton last night that his services are no longer needed at the White House.” The president added, “I disagreed strongly with many of his suggestions, as did others in the Administration, and therefore I asked John for his resignation, which was given to me this morning. I thank John very much for his service.”
Bolton disputed the president’s version of events in his own post on social media just 12 minutes later, writing, “I offered to resign last night, and President Trump said, ‘Let’s talk about it tomorrow’,” he wrote.
The tensions between the two men only deepened after Bolton left office.
Last October, Bolton was indicted by a federal grand jury in Maryland on 18 counts related to the alleged mishandling of classified information. (RELATED: Former National Security Adviser John Bolton Indicted)
The 26-page indictment alleged that Bolton shared more than 1,000 pages of information about his activities as National Security Advisor — including material classified up to the TOP SECRET/SCI level — with two unauthorized individuals. Prosecutors alleged that Bolton routinely transcribed handwritten notes about his daily activities into “diary-like” electronic documents and distributed them to the pair. (RELATED: FBI Raids John Bolton’s Home In National Security Investigation)
According to the indictment, a cyber actor believed to be associated with the Islamic Republic of Iran later hacked Bolton’s email account after he left government service and gained access to the information.
John Bolton Reportedly Pleads Guilty To Mishandling Classified Materials https://t.co/ABQFArnPqy
— Daily Caller (@DailyCaller) June 4, 2026
Prosecutors further alleged that when a representative for Bolton notified the government of the cyberattack in July 2021, the disclosure did not reveal that the compromised account contained classified national defense information or that the material had been shared with others.
Bolton was charged with eight counts of transmitting national defense information and 10 counts of unlawfully retaining national defense information. The investigation included an Aug. 22 FBI raid on Bolton’s Washington, D.C., office, where agents recovered documents marked “confidential” and “secret,” including some containing references to weapons of mass destruction, according to a September court filing. A simultaneous search of his Maryland home did not uncover classified materials.
🚨WATCH: John Bolton returns to his Bethesda, MD home more than 7 hours after the FBI raid began. pic.twitter.com/ojNx0efcOy
— Off The Press (@OffThePress1) August 22, 2025
After years of scrutiny over his handling of classified information, Bolton ultimately agreed to plead guilty to a single count of unlawful retention of sensitive national security documents and pay a fine exceeding $2 million. (RELATED: John Bolton Reportedly Pleads Guilty To Mishandling Classified Materials)
In 2021, the Department of Justice (DOJ) under former President Joe Biden dropped an investigation into whether Bolton had improperly disclosed classified information in his 2020 memoir. During President Trump’s first term, however, the Justice Department sought to block publication of the book and filed a lawsuit against Bolton over concerns that it contained classified information.
The book offered a scathing critique of the Trump administration, portraying the president as primarily focused on reelection and sharply criticizing his approach to governing and foreign policy.
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