How the Trump-Bolton relationship devolved into chaos and an FBI raid

The latest: The raid on Bolton's home was part of a national security probe into classified information, according to the New York Post, which first reported the news.

• The FBI's search happened as Trump has aggressively wielded the power of the presidency to punish political foes.

What they're saying "Not a fan, he's sort of a lowlife," Trump told the White House press pool about the Bolton raid. "He's a very quiet person, except on television if he can say something bad about Trump. Not a smart guy, could be a very unpatriotic guy. We're going to find out."

Context: Bolton was highly critical of Trump during the president's first term and has continued to scold the president on social media and in interviews during Trump 2.0.

• In fact, on Friday morning, before news broke of the FBI raid, Bolton shared skepticism in an X post about Russia-Ukraine peace talks.
• "Trump wants a Nobel Peace Prize, but I don't see these talks making any progress," he wrote.

Here's a look at how the Trump-Bolton relationship devolved after Trump had named him a top adviser.

Before the White House

Flashback: Bolton, seen as a Republican foreign policy hawk, was highly supportive of Trump during Fox News interviews as Trump took office the first time.

• Bolton appeared to support the president's foreign policy plans, with some seeing him as a good match for the president.

March 2018: Trump and Bolton team up

Trump eventually appointed Bolton, who served as a U.N. Ambassador under President George W. Bush, to be national security adviser.

• Bolton replaced H.R. McMaster, who was brought in to replace Michael Flynn, who had been dismissed after less than a month in office.

In May 2018, Trump announced the withdrawal from the Iranian nuclear deal, which was a position championed by Bolton, per AP.

• Bolton had been a driving force behind Trump's "maximum pressure" campaign on Iran.

November 2018: Bolton's ally ousted

Bolton's ally and deputy national security adviser Mira Ricardel was forced out of her position after Melania Trump's office called for her ouster following an alleged clash between the two.

• Bolton reportedly told his staff in an email at the time that he was "deeply grateful for all Mira has done on behalf of the NSC, her deep knowledge of the national security issues we confront daily, and her unwavering commitment to the president."

Summer 2019: Bolton's resistance to Trump

Public comments about North Korea in May 2019 appeared to show some disconnect between Trump and Bolton.

• According to the AP, Bolton suggested that a weapons test from North Korea violated U.N. Security Council resolutions.
• Trump appeared to "undercut" Bolton by saying he wasn't upset over North Korea testing the weapons, according to the AP.

Trump and Bolton's relationship appeared to fracture more as Bolton showed resistance to peace talks with Afghanistan. Trump had teased at the time he would host the Taliban at Camp David as a part of the peace negotiations.

• Trump scrapped the idea but still secretly raged over the internal disagreement, Axios reported.
• One source told Axios in 2019 that Bolton is "the dog who caught the car," and that his differing opinions on North Korea, Syria and his strong will did not sit well with Trump.

The bottom line: Bolton had showed disagreements with Trump over global policy moves, and that didn't seem to sit well with the president.

September 2019: Bolton's chaotic White House exit

Bolton had a turbulent exit from the White House.

• On Sept. 10, 2019, Trump tweeted that he asked Bolton to resign from his position. Minutes later, Bolton tweeted that he offered Trump his resignation the night before.
• Both sides offered different accounts of how Bolton's exit played out, with a timeline of events shared by sources with Axios. It was a sign to many at the time about how Trump ran his first administration.

Not long after his exit, it was reported that Bolton planned a memoir about his time in the White House, titled "The Room Where It Happened."

• The White House delayed the book's publication in order to could review its contents.

June 2020: Bolton's memoir battle

Bolton's memoir instantly made headlines as it chronicled inside the room details about Trump's foreign policy decisions.

• Among several details, the book claimed Trump had linked Ukraine aid to investigations of his political rivals, which was one of the core parts of Trump's first impeachment inquiry.
• As Axios' Mike Allen put it, "There has never been — and may never be — another book like this. Trump's national security adviser took hyper-detailed, real-time notes, and is sharing them with the world just nine months after leaving."

Trump pushed back against the book at the time, telling the Wall Street Journal that Bolton was "a lair" and "everybody in the White House hated John Bolton."

• "He wasn't liked at all and wasn't respected very much, and as we got to know him, he was respected less and less. Personally, I thought he was crazy."

June 2020: Trump's DOJ takes aim at Bolton's book

The Justice Department asked a federal judge for an emergency temporary restraining order against the book's publication.

• The Trump administration claimed in court the former national security adviser breached his contract because he didn't submit the book for a pre-publication review for classified information.
• But extensive excerpts had already been published and news organizations already had copies.

• A federal judge ruled that Bolton could publish the book, but opined that Bolton "likely published classified materials" and "exposed his country to harm and himself to civil (and potentially criminal) liability."

In 2021, the DOJ under the Biden administration shut down a criminal investigation into Bolton.

2020: Bolton's book and the world

Bolton's memoir resonated globally, as his inside-the-Oval revelations raised eyebrows from allies like South Korea and Europe about Trump.

Worth noting: "And if Trump wins a second term, Bolton's book will have an even longer shelf life," Axios alum Jonathan Swan wrote in 2020. "Bolton goes further than anyone has in describing the tactics that foreign leaders and Trump's own aides use to manipulate him."

August 2022: Iran's threats against Bolton

Years after his White House exit and memoir release, Bolton faced death threats from Iran after being critical of the regime there.

• In August 2022, an Iranian national was charged in connection with a plot to assassinate Bolton.

June 2022: Bolton defends Trump over Jan. 6

Bolton became a guest on news talk shows after following his White House departure. And in June 2022, he appeared to defend Trump in an interview with CNN by rejecting the notion that the Jan. 6 Capitol riot was a "carefully planned coup."

• "That's not the way Donald Trump does things," Bolton told CNN's Jake Tapper. "It's rambling from one … idea to another, one plan that falls through, and another comes up."
• "Ultimately, he did unleash the rioters at the Capitol. As to that, there's no doubt," he added.
• "As somebody who has helped plan coup d'état, not here but other places, it takes a lot of work, and that's not what he did," he added.

April 2023: Bolton harsh on Trump

Bolton's criticism of Trump continued into 2023, when he told CBS News in an interview that it was "a big mistake politically for Republicans" to align with Trump for the 2024 election.

• "It goes to the question of character and fitness for the presidency," Bolton said.

January 2024: Bolton's predictions for Trump's second term

Bolton's book made the rounds again when a paperback edition published in 2024.

• In the new edition's forward, Bolton wrote that "a mountain of facts demonstrates that Trump is unfit to be President."
• He wrote that he was worried Trump would remove the U.S. from NATO, abuse power to target political rivals and ignite a constitutional crisis, among other predictions.
• In response, then-Trump campaign spokesperson Jason Miller told Axios at the time: "For someone who professes to have such great disdain for President Trump, 'Book Deal Bolton' sure has found a way to grift off the relationship."

January 2025: Trump strips Bolton's security protections

Once Trump returned to the White House, he stripped multiple political adversaries of their security protections. Bolton was one of them.

• "This is a matter that people should take seriously," Bolton told CNN's Jake Tapper at the time.
• "It's certainly a downer for expressing your opposition to Donald Trump," Bolton said on CNN.

August 2025: FBI raid on Bolton's home

Details: A federal magistrate judge in Maryland approved the search of Bolton's home, according to ABC News.

• Bolton said he was unaware of the FBI activity, per CNN. and he was not detained or charged with any crimes.

More from Axios:

First look: John Bolton's predictions for a second Trump term

FBI raids former National Security Adviser John Bolton's home: Reports

John Bolton says he helped plan foreign coups