FBI agents left John Bolton’s office in Washington after obtaining documents. (Fox News Digital/Emma Woodhead)
"He’s a very quiet person, except on television, if he can say something bad about Trump," Trump added. "He's not a smart guy, but he could be a very unpatriotic guy. We’re going to find out."
The remarks echo years of past comments the pair have shared in public forums airing their dissatisfactions with one another, most notably after Trump tapped Bolton to serve as his national security advisor in 2018.
Fox News Digital took a look back at the pair's relationship since Trump's mad dash to fill his first administration in 2017, through his ouster of Bolton as the national security advisor and the ongoing clashes the pair have shared since.
TRUMP–BOLTON FEUD BACK IN FOCUS AFTER FBI RAID: 'NEVER HAD A CLUE … WHAT A DOPE!'
"I like (Bolton)," Trump said in 2015 while appearing on "Meet the Press" just weeks after announcing his candidacy for the White House. "I think he’s, you know, a tough cookie, knows what he’s talking about."
John Bolton served as President Trump's national security advisor from 2018 to 2019, for a total of about 17 months. (Jabin Botsford/The Washington Post via Getty Images)
The warm relationship got cozier when Trump announced in 2018 on X that he called on Bolton to serve as his national security advisor
"I am pleased to announce that, effective 4/9/18, @AmbJohnBolton will be my new National Security Advisor. I am very thankful for the service of General H.R. McMaster who has done an outstanding job & will always remain my friend. There will be an official contact handover on 4/9."
"I didn’t really expect that announcement this afternoon," Bolton said on Fox News shortly after the announcement. "But it’s obviously a great honor and always an honor to serve our country."
FBI agents load bags into a vehicle after conducting a search at the Washington, D.C., office of former National Security Advisor John Bolton on Aug. 22, 2025. (Fox News Digital/Emma Woodhead)
Bolton was ousted from his role as national security advisor Sept. 10, 2019, with Trump characterizing the departure as a firing, and Bolton saying he tendered his resignation and was not fired.
JOHN BOLTON'S HOME RAIDED BY FEDERAL AGENTS, SOURCES SAY
"I informed John Bolton last night that his services are no longer needed at the White House," Trump tweeted in 2019. "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. I will be naming a new National Security Advisor next week."
Bolton shot back on X that he "offered to resign last night and President Trump said, ‘Let’s talk about it tomorrow.'"
The former national security advisor was replaced by Robert C. O'Brien, with Trump and Bolton continuing their contentious relationship years later.
The raid on Bolton's home is part of the "early stages of an ongoing investigation into John Bolton," Vice President JD Vance said Friday during an appearance on "Meet the Press." Bolton was not arrested or in custody amid the early morning raids.
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The searches are focused on potential classified documents agents believe Bolton may still possess, Fox News reported.
https://www.foxnews.com/politics/history-how-trump-boltons-relationship-fell-tatters