A look back at Trump and Bolton’s tumultous relationship

As FBI agents on Friday searched the home and office of John Bolton, once a top adviser to the president, Donald Trump didn’t hold back, telling reporters: “I’m not a fan of John Bolton. He’s a real sort of a lowlife.”

At the same time, Trump said he knew nothing about the searches beforehand, which sources told ABC News are related to allegations that Bolton is in possession of classified records.

“I thought he was a sleazebag, actually,” Trump said in the Oval Office when asked about Bolton. “And he suffers major Trump derangement syndrome, but so do a lot of people and they’re not being affected by anything we do. I don’t know anything about it. I just saw that, I’ll find out about it.”

It was just the latest twist in Trump and Bolton’s rocky relationship that stretches back years and includes clashes as recent as this month over Bolton’s criticism of Trump’s summit with Russian President Vladimir Putin.

Bolton departed the first Trump administration in 2019 after long-simmering tensions with Trump. Bolton said at the time that he offered his resignation, while Trump said he had fired his national security adviser.

A year later, the Trump administration sued to try to block Bolton from publishing a memoir of his time inside the White House, claiming classified information included in it could potentially harm national security. A federal judge denied the administration’s attempt to block the book’s release, though the administration continued a civil suit against Bolton seeking the proceeds.

The Trump administration had also launched a criminal probe at the time over whether Bolton mishandled classified information. The Biden administration said in June 2021 that it had dropped the investigation, as well as the civil lawsuit.

In the tell-all book, Bolton characterized Trump as “stunningly uninformed” and easily manipulated by foreign adversaries.

In an exclusive interview with ABC News Chief Global Affairs Correspondent Martha Raddatz at the time of the book’s release, Bolton said of Trump, “I don’t think he’s fit for office. I don’t think he has the competence to carry out the job.”

After returning to the White House this past January, Trump revoked Bolton’s security clearance and canceled his security detail despite ongoing threats from Iran because of his work in the first Trump administration.

Defending his decision, Trump told reporters at the time “I think there was enough time. We take a job, you take a job, you want to do a job, we’re not going to have security on people for the rest of their lives.” He went on to call Bolton a “very dumb person.”

More recently, Bolton and Trump traded insults over Bolton’s disapproval of Trump’s decision to welcome Putin on American soil to discuss the Russia-Ukraine war.

Bolton said Trump had made a “mistake” in inviting Putin to Alaska and questioned his strategy on peace talks during an Aug. 10 appearance on ABC’s “This Week.” Trump fired back on social media, slamming what he said was “unfair media coverage” of the summit including “[c]onstantly quoting fired losers and really dumb people like John Bolton.”

During his interview on “This Week,” Bolton was also asked about what has been characterized as Trump’s retribution efforts and whether he was worried about being a target.

Bolton responded, “I think it is a retribution presidency.”

Vice President JD Vance, in an exclusive interview with NBC’s “Meet the Press with Kristen Welker,” said the FBI search of Bolton’s property on Friday was not politically motivated.

“Well, so we’re in the very early stages of an ongoing investigation into John Bolton. I will say we’re gonna let that investigation proceed. What I can tell you is that unlike the Biden DOJ and the Biden FBI, our law enforcement agencies are going to be driven by law and not by politics,” Vance said.