Dispute Over MAGA Hat Could Affect Trump’s Choice for Top Military Adviser
The president recounted that Dan Caine had once offered to kill for him and placed a signature red hat on his head, which was a breach of military rules.
TroibNews 
The initial major challenge facing Donald Trump’s selection for top military adviser isn't the ongoing Ukraine-Russia conflict or his qualifications, but rather the story surrounding a red MAGA hat.
Trump's candidate for the chair of the Joint Chiefs has transitioned from retirement to the military's highest-ranking general. However, the account Trump shares of retired Lt. Gen. Dan ‘Razin’ Caine wearing a politically branded hat during their 2018 encounter in Iraq could breach military protocols, complicate the confirmation process, and damage his credibility.
According to Trump, Caine expressed his admiration by saying he “loved” him and would “kill for you,” before placing a MAGA hat on Trump’s head.
This narrative highlights how loyalty to the president can offer both benefits and risks, even if the loyalty is entirely fictitious.
Caine has remained silent about the incident, but a military official familiar with him and the encounter has denied it.
“He's never touched a MAGA hat,” the official stated, confirming previous reports regarding the discrepancy and speaking under the condition of anonymity due to the sensitive nature of the topic. “I’ve known him for a decade. Never heard him say anything political or partisan.”
Trump’s remarks, while typical of his exaggerated storytelling, carry significant implications for a service member bound by the Constitution to provide nonpolitical and nonpartisan guidance to civilian leaders.
Caine will be required to clarify the situation, stated Sen. Jack Reed, the leading Democrat on the Senate Armed Services Committee. “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 has responded to requests for comment.
The meeting in Iraq took place during Caine's deployment as a one-star general in the campaign against ISIS. Serving as deputy commanding general of a special operations task force, he was vital in the American-led operations and helped coordinate air support for Kurdish and Iraqi forces.
Trump has frequently mentioned his fascination with Caine’s pilot call sign, Dan ‘Razin’ Caine.
“During my first term, ‘Razin’ was instrumental in the complete annihilation of the ISIS caliphate,” Trump wrote on Truth Social last week when he announced 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.”
Trump brought up the MAGA hat episode most recently at last year’s Conservative Political Action Committee conference. “I’ll kill for you, sir,” he recalled Caine saying. "Then he puts on a Make America Great Again hat.”
Additionally, Trump stated that other service members had donned MAGA hats during the same trip. “I said, ‘You're not supposed to do that. You know that.’ They said, ‘It's OK, sir. We don't care.’"
Resolving the truth of the matter could complicate Caine’s confirmation hearings.
However, controversies have not derailed most of Trump’s other nominees. For instance, Defense Secretary Pete Hegseth was confirmed despite facing unproven allegations of assault, excessive drinking, and financial mismanagement.
“He's going to be asked about it,” remarked Sen. Dan Sullivan, a senior member of the Senate Armed Services Committee. “He'll go through the normal vetting … we are going to have a patriotically apolitical, stridently constitutional military.”
Caine, who retired last year after a career flying F-16s, would need to revert to active duty, be promoted from three to four stars, and receive a presidential waiver for the position, given that he has never led a combatant command or a service branch.
“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, a member of the Senate Armed Services Committee. “It would violate the most basic kind of code and would probably result in discipline within the military.”
The role of Joint Chiefs chair is distinct. The general provides the president with primary military advice, delivering apolitical counsel on diverse matters ranging from overseas deployments to leadership selections.
This task is challenging under any administration, but could be especially difficult with Trump, who has had contentious interactions with his previous Joint Chiefs Chair, Gen. Mark Milley, and terminated Chair C.Q. Brown earlier this month along with five other military leaders. Recently, Trump suggested he would also dismiss military officers associated with the U.S. withdrawal from Afghanistan.
Caine would also need to collaborate with a newly appointed Defense Secretary lacking high-level Pentagon experience. Pete Hegseth, a former Fox TV personality, has joined the Defense Department as it confronts the accelerating military expansion of China.
“It is helpful that [Caine] is coming in with an enormously competent vice chairman,” stated 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.”
Trump's focus on “Razin” also reflects his affinity for nicknames. For instance, he referred to his first Defense Secretary as James “Mad Dog” Mattis — a moniker that the four-star general detested. The relationship deteriorated over Trump’s insistence on withdrawing U.S. troops from Syria, ultimately leading to Mattis's resignation.
Max Fischer contributed to this report for TROIB News
Trump's candidate for the chair of the Joint Chiefs has transitioned from retirement to the military's highest-ranking general. However, the account Trump shares of retired Lt. Gen. Dan ‘Razin’ Caine wearing a politically branded hat during their 2018 encounter in Iraq could breach military protocols, complicate the confirmation process, and damage his credibility.
According to Trump, Caine expressed his admiration by saying he “loved” him and would “kill for you,” before placing a MAGA hat on Trump’s head.
This narrative highlights how loyalty to the president can offer both benefits and risks, even if the loyalty is entirely fictitious.
Caine has remained silent about the incident, but a military official familiar with him and the encounter has denied it.
“He's never touched a MAGA hat,” the official stated, confirming previous reports regarding the discrepancy and speaking under the condition of anonymity due to the sensitive nature of the topic. “I’ve known him for a decade. Never heard him say anything political or partisan.”
Trump’s remarks, while typical of his exaggerated storytelling, carry significant implications for a service member bound by the Constitution to provide nonpolitical and nonpartisan guidance to civilian leaders.
Caine will be required to clarify the situation, stated Sen. Jack Reed, the leading Democrat on the Senate Armed Services Committee. “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 has responded to requests for comment.
The meeting in Iraq took place during Caine's deployment as a one-star general in the campaign against ISIS. Serving as deputy commanding general of a special operations task force, he was vital in the American-led operations and helped coordinate air support for Kurdish and Iraqi forces.
Trump has frequently mentioned his fascination with Caine’s pilot call sign, Dan ‘Razin’ Caine.
“During my first term, ‘Razin’ was instrumental in the complete annihilation of the ISIS caliphate,” Trump wrote on Truth Social last week when he announced 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.”
Trump brought up the MAGA hat episode most recently at last year’s Conservative Political Action Committee conference. “I’ll kill for you, sir,” he recalled Caine saying. "Then he puts on a Make America Great Again hat.”
Additionally, Trump stated that other service members had donned MAGA hats during the same trip. “I said, ‘You're not supposed to do that. You know that.’ They said, ‘It's OK, sir. We don't care.’"
Resolving the truth of the matter could complicate Caine’s confirmation hearings.
However, controversies have not derailed most of Trump’s other nominees. For instance, Defense Secretary Pete Hegseth was confirmed despite facing unproven allegations of assault, excessive drinking, and financial mismanagement.
“He's going to be asked about it,” remarked Sen. Dan Sullivan, a senior member of the Senate Armed Services Committee. “He'll go through the normal vetting … we are going to have a patriotically apolitical, stridently constitutional military.”
Caine, who retired last year after a career flying F-16s, would need to revert to active duty, be promoted from three to four stars, and receive a presidential waiver for the position, given that he has never led a combatant command or a service branch.
“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, a member of the Senate Armed Services Committee. “It would violate the most basic kind of code and would probably result in discipline within the military.”
The role of Joint Chiefs chair is distinct. The general provides the president with primary military advice, delivering apolitical counsel on diverse matters ranging from overseas deployments to leadership selections.
This task is challenging under any administration, but could be especially difficult with Trump, who has had contentious interactions with his previous Joint Chiefs Chair, Gen. Mark Milley, and terminated Chair C.Q. Brown earlier this month along with five other military leaders. Recently, Trump suggested he would also dismiss military officers associated with the U.S. withdrawal from Afghanistan.
Caine would also need to collaborate with a newly appointed Defense Secretary lacking high-level Pentagon experience. Pete Hegseth, a former Fox TV personality, has joined the Defense Department as it confronts the accelerating military expansion of China.
“It is helpful that [Caine] is coming in with an enormously competent vice chairman,” stated 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.”
Trump's focus on “Razin” also reflects his affinity for nicknames. For instance, he referred to his first Defense Secretary as James “Mad Dog” Mattis — a moniker that the four-star general detested. The relationship deteriorated over Trump’s insistence on withdrawing U.S. troops from Syria, ultimately leading to Mattis's resignation.
Max Fischer contributed to this report for TROIB News
