El Chisme

In at least one retelling of Caine and Trump's first meeting in Iraq in 2018, the president has seemed to indicate Caine was wearing a red MAGA hat, something that would not be allowed under military rules.

The question was posed by some senators at Caine's confirmation hearing before the Senate Armed Services Committee.

"Let me start off by asking about some hyperbole that may have been out there in the press," Sen. Roger Wicker, R-Miss., said at the start of Tuesday's hearing. "Gen. Caine, did you wear a MAGA hat in front of the president?"

"No, sir," he responded.

He provided the same answer when asked by Wicker, "Did you wear a MAGA hat at any time?"

And when pressed by Wicker, Caine said, "Sir, for 34 years, I've upheld my oath of office and my commitment to my commission, and I have never worn any political merchandise."

When Sen. Jack Reed, D-R.I., the ranking member on the committee, followed up with the same line of questioning, Caine answered, "As I mentioned to the chairman, for 34 years, I've upheld my oath of office and in the responsibilities of my commission.

"I think I went back and listened to those tapes, and I think the president was actually talking about somebody else," Caine said. "And I've never worn any political merchandise or said anything to that effect."

Trump's story about how he first met Caine has evolved over the years since he first mentioned Caine during remarks at the Conservative Political Action Conference in February 2019, shortly after his trip to Iraq the previous year.

Trump has repeatedly given Caine credit for ending the war against the Islamic State and in his first recounting of their meeting noted how Caine became memorable to him for saying that ISIS could be destroyed in weeks by quickly striking strongly at its last remaining pieces of territory in Syria, something Trump said his advisers in Washington argued could still take years. PHOTO: Lt. General John D. Caine takes his seat as he arrives for a Senate Armed Services Committee hearing on his nomination to be the Chairman of the Joint Chiefs of Staff on Capitol Hill in Washington, April 1, 2025.

In that first retelling, Trump jokingly focused on how he was struck by the general's call sign "Razin," asking if it was a reference to the raisin fruit.

Trump continued to tell a version of that story over the years, but at last year's CPAC, where he again brought up that first encounter with Caine, the president appeared to state that Caine was wearing a red MAGA hat at the time.

However, it was unclear if Trump was referring to Caine or to a sergeant because in the transcript of those remarks, he first mentioned meeting Caine, whom he referred to as general and asked his name.

Then, according to the transcript, Trump appeared to ask a sergeant his name, who in turn told him, according to Trump, "Yes, sir. I love you, sir. I think you're great, sir. I'll kill for you, sir."

Then he puts on a "Make America Great Again" hat, as did hundreds of other service members in Trump's retelling.

"And they're not supposed to do this, but they all put on the 'Make America Great Again' hat, right? Not supposed to do it. I said, you're not supposed to do that. You know that. They said, 'It's OK, sir. We don't care,'" Trump said.

The wearing of political merchandise by military service members is not allowed as it is a tenet of an apolitical military.