President Trump plans to nominate retired Air Force Lieutenant General Dan Caine as chairman of the Joint Chiefs of Staff after dismissing General Charles Q. Brown Jr. Trump praised Caine, citing his extensive military background and achievements, including his work at the CIA and hands-on combat experience. The two first met in 2018, where Caine allegedly claimed the Islamic State could be defeated in a week, countering senior advisers’ predictions. Trump recounted their meeting, noting Caine supposedly wore a MAGA hat, though Caine has denied this. Trump’s recollection of their encounter has evolved over the years, changing details each time.
According to President Trump, Dan Caine, the retired Air Force lieutenant general he aims to appoint as his next chairman of the Joint Chiefs of Staff, left a strong impression on him during their initial meeting in 2018.
The general informed the president that the Islamic State wasn’t as formidable as believed and could be eliminated in a week, countering a prediction from senior advisers that it would take two years, as recounted by Mr. Trump in 2019.
At a Conservative Political Action Conference meeting last year, Mr. Trump mentioned that General Caine wore a Make America Great Again hat while meeting him in Iraq. (However, General Caine has told aides that he has never worn a MAGA hat.)
On Friday, Mr. Trump announced that he would nominate General Caine following the dismissal of Gen. Charles Q. Brown Jr., a four-star fighter pilot known as C.Q.
“I am proud to announce that I am nominating Air Force Lieutenant General Dan ‘Razin’ Caine as the next Chairman of the Joint Chiefs of Staff,” Mr. Trump stated in a message on Truth Social. “General Caine is an accomplished pilot, national security expert, successful entrepreneur, and a ‘warfighter’ with extensive interagency and special operations experience.”
General Caine graduated from the Virginia Military Institute in 1990, obtaining a degree in economics, and later earned a master’s degree in air warfare from American Military University.
An F-16 pilot with 150 combat flight hours, General Caine’s trajectory is notable for a future Air Force general.
He served as a White House fellow at the Agriculture Department and was a counterterrorism specialist on the White House’s Homeland Security Council during President George W. Bush’s tenure. He has held several covert intelligence and special operations roles, both domestically and internationally.
As detailed in his military biography, General Caine was a part-time member of the Air National Guard from 2009 to 2016 and was described as “a serial entrepreneur and investor.”
He also served as an associate director for military affairs at the C.I.A. from 2021 to 2024, acting as the primary liaison to the Pentagon and collaborating with the military on various classified programs and operations, as reported by former colleagues.
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 mentioned that he worked closely with the general during his C.I.A. tenure, noting his effectiveness in that role.
While at the C.I.A. in 2023, General Caine reflected on his experience as chief of weapons and tactics for the 121st Fighter Squadron at Andrews Air Force Base on Sept. 11, 2001. This marked the first deployment of fighter jets over Washington following the terrorist attacks.
“We jumped in the airplanes and started them up,” General Caine recounted in a reflection posted by the C.I.A. “As my plane powered up, the generators activated, and the radios became chaotic. Emergency channels warned that ‘anyone around Washington, D.C., will be shot down.’ I thought to myself: ‘Wait. That’s me who will be doing the shooting.’”
“My aircraft was loaded with weapons including a 20-millimeter gun and two heat-seeking missiles,” he continued. “I was airborne for about 7.5 to 8 hours that day.”
President Trump’s recounting of his first meeting with General Caine has evolved over time. In his initial public account during the Conservative Political Action Conference in 2019, he indicated that they met during his trip to Iraq.
“I asked him, ‘What’s your name?’” Mr. Trump recalled. “‘Sir, my name is Razin.’”
“‘Raisin, like the fruit?’” Mr. Trump said he queried. “‘What’s your last name?’”
“‘Caine,’” Mr. Trump quoted the officer’s reply. “‘Razin Caine.’”
This was when Mr. Trump claimed the general stated he could defeat the Islamic State within a week.
“‘One week?’” Mr. Trump expressed 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 strike them from behind, from the sides, from everywhere, including the base you’re currently at, sir,’” Mr. Trump recalled the general as saying. “‘They won’t know what hit them.’”
Mr. Trump further mentioned that General Caine indicated that his superiors came from Washington and neglected the opinions of their commanders in the field, adding, “you’re the first one to ask us our opinion.”
Five years later, Mr. Trump revisited that encounter at another CPAC meeting, this time claiming General Caine asserted that the Islamic State could be defeated in four weeks instead of one.
The president also introduced a new detail, alleging that General Caine wore a MAGA hat during their meeting, despite military rules prohibiting active-duty personnel from displaying political symbols.
“‘I love you, sir. I think you’re great, sir. I’ll kill for you, sir,’” Mr. Trump recounted General Caine saying. “Then he puts on a Make America Great Again hat,” Mr. Trump added, chuckling. “You’re not allowed to do that, but they went ahead and did it.”