Maga Hat Drama Could Taint Trump’s Top Military Adviser Pick

The first big challenge for Donald Trump’s top military adviser pick isn’t the Ukraine-Russia war or even his lack of qualifications. It’s the legend about a red MAGA hat.

Trump’s choice for the Joint Chiefs chair has emerged from obscurity — and retirement — to be the military’s top general. But the story Trump tells about retired Lt. Gen. Dan ‘Razin’ Caine donning a politically affiliated ball cap when they met in Iraq in 2018 could violate military rules, muddy his confirmation process and taint his credibility.

The way Trump explains it, Caine told the president he “loved” him and would “kill for you” before slapping a MAGA hat on his head.

The story underscores how allegiance to the president can carry both advantages and perils — even if that allegiance is entirely made up.

Caine has not commented publicly on the incident, but a military official who has served with him and has knowledge of the encounter denied it.

“He's never touched a MAGA hat,” said the official, who confirmed reports last week about the discrepancy and was granted anonymity to wade into a contentious issue. “I’ve known him for a decade. Never heard him say anything political or partisan.”

Trump’s comments, while not beyond his usual exaggerated anecdotes, carry a deeper weight for a servicemember, who is bound by the Constitution to deliver nonpolitical, nonpartisan guidance to civilian superiors.

Caine will have to “explain what happened,” said Sen. Jack Reed (D-R.I.), the Senate Armed Services Committee’s top Democrat. “If it happened the way the president said, well, that's completely unprofessional. And that, I think, would question his ability to stand up to the president.”

Neither Caine, the Pentagon nor the White House responded to a request for comment.

The Iraq meeting occurred when Caine was deployed as a one-star general in the fight to defeat ISIS. His role as deputy commanding general of a special operations task force put him at the forefront of the American-led operation, and he helped coordinate the air war that supported Kurdish and Iraqi fighters.

Trump said he was immediately fascinated with Caine’s pilot call sign name: Dan ‘Razin’ Caine. The president has mentioned it repeatedly since.

“During my first term, ‘Razin’ was instrumental in the complete annihilation of the ISIS caliphate,” Trump posted on Truth Social last week when announcing his decision. “It was done in record setting time, a matter of weeks. Many so-called military ‘geniuses’ said it would take years to defeat ISIS. General Caine, on the other hand, said it could be done quickly, and he delivered.”

The president mentioned the MAGA hat incident most recently during last year’s Conservative Political Action Committee conference. “I’ll kill for you, sir,” Trump recalled the general saying. "Then he puts on a Make America Great Again hat.”

Trump also said that, on the same trip, other servicemembers donned MAGA hats. “I said, ‘you're not supposed to do that. You know that.’ They said, ‘It's OK, sir. We don't care.’"

Determining what actually happened will likely make Caine’s confirmation hearing more challenging.

But controversies haven’t fatally wounded most of Trump’s other nominees. Defense Secretary Pete Hegseth, for example, was confirmed despite allegations he denied of assault, excessive drinking and financial mismanagement.

“He's going to be asked about it,” said Sen. Dan Sullivan (R-Alaska.), a Senate Armed Services Committee senior member. “He'll go through the normal vetting … we are going to have a patriotically apolitical, stridently constitutional military.”

Caine retired from the service last year after a career as an F-16 pilot with stints in the Pentagon and the CIA. He would need to return to uniform, be promoted from three to four stars and receive a presidential waiver to take the role, since he also has not led a combatant command or a branch of the armed services.

It would be disqualifying “for an active-duty member of the United States military to put on a blatantly political piece of clothing while in uniform,” said Sen. Richard Blumenthal (D-Conn.), a Senate Armed Services Committee member. “It would violate the most basic kind of code and would probably result in discipline within the military.”

The Joint Chiefs chair is a unique position. The general serves as the president’s primary military adviser, giving the commander-in-chief apolitical advice on everything from overseas deployments to leadership appointments.

It’s a difficult role under any administration. But it could prove especially so with Trump, who clashed with his outspoken former Joint Chiefs Chair Gen. Mark Milley and fired Chair C.Q. Brown this month along with five other military leaders. Trump on Wednesday hinted that he also would fire military officersinvolved in the American withdrawal from Afghanistan.

And Caine would need to work with an untested Defense secretary who has no high-level Pentagon experience. Pete Hegseth, a former Fox TV personality, joins as the Defense Department seeks to counter the rapid growth of China’s military.

“It is helpful that [Caine] is coming in with an enormously competent vice chairman,” said Seth Jones, a former military adviser and current defense expert at the Center for Strategic and International Studies, referring to Joint Chiefs Vice Chair Adm. Christopher Grady. “It’s a pretty formidable joint staff.”

The president’s focus on “Razin” also speaks to his penchant for nicknames. He referred to his first Defense secretary as James “Mad Dog” Mattis — a term the four-star general hated. The relationship soured over Trump’s demand that the U.S. pull troops out of Syria. Mattis ultimately resigned.