General ‘Razin’ Caine vaults into the top tier of Trump advisers
The new chairman of the Joint Chiefs of Staff has won over Donald Trump in his short stint in the job, emerging as one of the President’s closest confidantes.
As President Trump and his top aides weighed a military operation against Iran in early June, Vice President JD Vance and Secretary of State Marco Rubio wanted to ensure that American troops wouldn’t end up entangled indefinitely in another Middle East war.
Gen. Dan Caine, the newly confirmed chairman of the Joint Chiefs of Staff, shared the concern of others in the room about putting Americans in harm’s way. He pulled out a map in the Situation Room and explained how, if ordered to strike Iran’s nuclear facilities, the Pentagon could protect the pilots involved in the mission and defend U.S. troops in the Middle East from any Iranian retaliation.
Caine’s confidence resonated with Trump. When the June 21 attack unfolded largely in line with the options Caine outlined, it magnified his influence with a president whose previous handpicked military advisers had often proved to be obstacles to his goals. In less than a week following the operation, Caine has addressed the public twice and enjoyed lavish praise from the president.
“I have to say, General ‘Razin’ Caine was incredible,” Trump told reporters Wednesday, using Caine’s Air Force nickname and describing his role in the Iran operation. Instead of calling Caine “general” or “Dan,” Trump sometimes calls him “Razin.” This article is based on interviews with nine U.S. officials, a campaign official and two people close to Vance.
In his short stint in the new job, Caine has emerged as one of Trump’s closest advisers. In the week before and immediately following the strike, the general was in the White House nearly every day. During Saturday night’s operation in the Situation Room, Trump repeatedly turned to Caine for answers to his questions. Caine narrated the attack as it played out, displaying maps and explaining what was going on in real time. He told White House officials that he believed the Iranians never saw them coming, and answered the most questions of any official in the room.
Trump looks to Caine for the straight facts about what is going on, said one senior U.S. official.
“General Caine is detail-oriented and ruthlessly focused on carrying out President Trump’s military objectives,” Vance said in a statement to The Wall Street Journal. “After about two months on the job, General Caine helped oversee a series of incredibly precise airstrikes that resulted in zero American casualties and the obliteration of Iran’s nuclear capabilities. I think the best way to judge his job performance is by its results, and America is safer and stronger thanks to the successful operation he oversaw last weekend.” The question for Caine now is whether he can navigate the difficult line between being a member of Trump’s inner circle and being an apolitical senior military adviser, the chairman’s usual role. Trump has soured spectacularly on retired Gen. Mark Milley, who served in Caine’s role during the president’s first term. In fact, Trump suggested on social media that Milley should be executed , and President Joe Biden pardoned Milley as one of his final acts in office out of a fear that Trump might try to prosecute the retired general one day.
On Thursday, during a press briefing with Defense Secretary Pete Hegseth, Caine avoided getting pulled into politics or offering much in the way of opinions. Hegseth spent much of his opening statement praising Trump and lambasting the news media for publishing the leak of a preliminary intelligence report’s assessment that the strike didn’t destroy the core components of Iran’s nuclear program.
When his turn came to speak, Caine stuck to the technical details. He gave a lengthy account of how the 30,000-pound bunker buster bomb was developed and explained how the Pentagon assessed the damage at the three sites. He veered into more Trumpian rhetoric only a few times, saying the personnel who defended Al Udeid Air Base in Qatar from a retaliatory Iranian missile attack on Monday “crushed it.” At one point, he was asked whether he had been pressured to massage his assessment to fit a political agenda. He quickly answered “no, I have not, and no, I would not.” Trump often extolled other generals tapped for senior posts during his first term, but almost all of them eventually fell out of favor, often over Trump’s tendency to trample on long-accepted guard rails for keeping the military out of politics.
Caine “has to help his civilian bosses be the best wartime leaders they can be,” said Peter Feaver, a professor of political science and public policy at Duke University. “Once they have made a decision, he must make sure the military faithfully executes all lawful orders. There is a risk that this will be misperceived as becoming politicized.” His rise from a largely unknown military officer to Trump’s team began at an air base in western Iraq in 2018. Caine, then the deputy commander of the special operations component of Operation Inherent Resolve, the campaign to defeat ISIS, helped brief Trump, who had flown in for a progress report on the war.
“He was impressed with Gen. Caine,” said one former senior military officer with knowledge of the meeting. “He was clearly impressed with how he communicated with the president, his straightforward approach to answering questions.”
At a 2024 fundraiser for top donors, Trump recalled meeting Caine. Other military leaders had told him during his first term that he couldn’t defeat ISIS quickly, according to audio of his remarks from last year reviewed by the Journal. According to Trump, Caine said he “could knock the hell out of them,” Trump said.
“I tell you this story because we have a great military, but they’re not allowed to perform because we have idiots that talk. We have stupid people running it,” Trump said.
Caine had spent much of his military career as an F-16 fighter pilot in the Air National Guard, deploying several times to the Middle East. He was assigned to Andrews Air Force Base on Sept. 11, 2001, when his unit was scrambled to protect the skies over Washington. Later, he worked on special operations tactics for stealth aircraft, as well as on highly classified programs at the Pentagon, Joint Special Operations Command and the Central Intelligence Agency.
After returning from his deployment to Iraq, he retired from the Air Force in 2024 as a three-star general, only months before Trump took office for his second term. After Trump returned to office, chief of staff Susie Wiles brought Caine to the White House for meetings for potential military jobs, and he was eventually brought back into the military and then nominated as chairman of the Joint Chiefs of Staff. In an overnight April vote, the Senate confirmed Caine to his role in a 60-25 vote.
Caine became the first retired officer and the first non-four-star general to serve as the Pentagon’s senior military officer.
Even before he took up the job, he had to fend off accusations that he was too close to Trump.
During his Senate confirmation hearing, he disputed a story Trump likes to tell about their 2018 meeting. According to Trump, Caine wore a MAGA hat and said “I would kill for you, sir.” Caine testified that he thought the president might have been talking about someone else.
“I’ve never worn any political merchandise or said anything to that effect,” he said.
John Bolton, Trump’s national security adviser from 2018 to 2019, said he never saw Caine wear a MAGA hat or say anything political during the 2018 trip to Iraq. “My impression of Caine was he would be a typical nonpolitical general that we would always strive to get [in the Joint Chiefs of Staff role],” Bolton said.
As Trump and his team debated the Iran strike in the White House Situation Room in the days before the strike, Caine outlined multiple military options rather than advocating for a course of action. During the week leading up to the attack Caine was at the White House daily, helping the administration plan its operational security procedures and how to keep the attack from becoming public. He visited the White House again on Monday for a postattack debriefing.
Until then, several aides said, he wasn’t a regular presence, and White House aides said they knew little about his background or life outside the government.
Trump has come to like the general because he is “succinct” and answers his questions quickly without any frills, said one White House official, adding “He doesn’t drone on and on. He gets to the point.” At a Pentagon press conference hours after the Iran strikes, Hegseth lavished praise on Trump for his “bold and brilliant operation” and declaring Iran’s nuclear ambitions “obliterated.” Caine, in his blue Air Force uniform, offered a meticulous recounting of the operation and a measured assessment of its success. The Iranian nuclear facilities hit by U.S. bombers “sustained extremely severe damage and destruction,” he said, but noted that a final assessment of the damage would take time.
He didn’t mention Trump once.
The Wall Street Journal
