In President Trump’s telling, Dan Caine, the retired Air Force lieutenant general whom he wants to be his next chairman of the Joint Chiefs of Staff, made an impression on him when the two men first met in 2018.
The general told the president that the Islamic State was not so tough and could be defeated in a week, not two years as senior advisers predicted, Mr. Trump recounted in 2019.
And at a Conservative Political Action Conference meeting last year, Mr. Trump said that General Caine put on a Make America Great Again hat while meeting with him in Iraq. (General Caine has told aides he has never put on a MAGA hat.)
On Friday, Mr. Trump said he would nominate General Caine after firing Gen. Charles Q. Brown Jr., a four-star fighter pilot known as C.Q.
“Today, I am honored to announce that I am nominating Air Force Lieutenant General Dan ‘Razin’ Caine to be the next Chairman of the Joint Chiefs of Staff,” Mr. Trump said in a message on Truth Social. “General Caine is an accomplished pilot, national security expert, successful entrepreneur, and a ‘warfighter’ with significant interagency and special operations experience.”
General Caine is a 1990 graduate of the Virginia Military Institute, where he received a degree in economics. He later got a master’s degree in air warfare at the American Military University.
An F-16 pilot with 150 combat flight hours, General Caine’s career took him on an unusual path for a future Air Force general.
He was a White House fellow at the Agriculture Department and a counterterrorism specialist on the White House’s Homeland Security Council under President George W. Bush. He served in several highly secretive intelligence and special operations assignments, some in the United States and some overseas.
According to his military biography, General Caine was a part-time member of the Air National Guard from 2009 to 2016 and “a serial entrepreneur and investor.”
He was also an associate director for military affairs at the C.I.A. from 2021 to 2024, serving as the principal liaison to the Pentagon and working with the military on several highly classified programs and operations, former colleagues said.
Gen. Kenneth F. McKenzie Jr., a former head of the military’s Central Command, described General Caine in an email as an “exceptionally talented officer.” General McKenzie said he worked closely with the general in his C.I.A. assignment, and that he was “very effective in that job.”
While at the C.I.A. in 2023, General Caine offered a reflection about his time as the chief of weapons and tactics attached to the 121st Fighter Squadron at Andrews Air Force Base, in Washington’s Maryland suburbs, on Sept. 11, 2001. After the terrorist attacks, fighter jets were deployed over Washington for the first time.
“We jumped in the airplanes and started them up,” General Caine recalled in a reflection on Sept. 11 posted by the C.I.A. “As my plane came to life, the generators came online, and the radios were going ballistic. People on the emergency channels were saying, ‘Anybody around Washington, D.C., will be shot down.’ I remembered thinking to myself: ‘Wait. That’s me that will be shooting.’”
“The weapons were loaded on my airplane so we’d have the 20-millimeter gun and two heat-seeking missiles,” he continued. “I was airborne for about 7.5 to 8 hours that day.”
Mr. Trump’s recounting of the time he met General Caine has changed over time. In his first known public telling of the story, at the Conservative Political Action Conference in 2019, he said the two met during his visit to Iraq.
“I said, ‘What’s your name?’” Mr. Trump recalled. “‘Sir, my name is Razin.’”
“‘Raisin, like the fruit?’” Mr. Trump said he asked. “‘What’s your last name?’”
“‘Caine,’” Mr. Trump said was the officer’s response. “‘Razin Caine.’”
That was when Mr. Trump said the general then told him he could defeat the Islamic State in a week.
“‘One week?’” Mr. Trump said he asked incredulously. “‘I was told two years!’”
“‘We’re only hitting them from a temporary base in Syria, but if you gave us permission, we could hit them from the back, from the side, from all over, from the base you’re right on right now, sir,’” Mr. Trump quoted him as saying. “‘They won’t know what the hell hit them.’”
Mr. Trump also said that General Caine told him that his superiors came from Washington but did not listen to their commanders in the field, and that “you’re the first one to ask us our opinion.”
Five years later, Mr. Trump spoke about that interlude at another CPAC meeting. This time, Mr. Trump said General Caine promised that the Islamic State could be defeated in four weeks, not one.
The president also added a new detail, claiming that General Caine donned a MAGA hat, despite military guidelines that active-duty troops should not wear political paraphernalia.
“‘I love you, sir. I think you’re great, sir. I’ll kill for you, sir,’” Mr. Trump said General Caine said. “Then he puts on a Make America Great Again hat,” Mr. Trump said, laughing. “You’re not allowed to do that, but they did it.”
