• Trump fired General Charles Q. Brown Jr. and nominated Lt. Gen. Dan Caine as Joint Chiefs chairman.
• Caine's background includes combat experience, entrepreneurship, and roles in national security.
• Experts say Caine may be missing important qualifications compared to past picks for chairman.

President Donald Trump has announced his intention to nominate venture capitalist and retired Air Force Lieutenant General Dan "Razin" Caine as the new Joint Chiefs of Staff chairman, after firing General Charles Q. Brown Jr. from the job Friday night.

While Trump praised Caine as a "national security expert" and "warfighter," he would be an unusual choice for the country's highest-ranking military leader.

The former fighter pilot is "a serial entrepreneur and investor," according to his military biography. He is now listed as a partner at Shield Capital, a venture capital firm.

Dan Caine and Shield Capital did not respond to requests for comment.

Donald F. Kettl, an emeritus professor and former dean of the University of Maryland School of Public Policy, told Business Insider that it was unusual for a president to appoint a retired general to head the joint chiefs, especially one with less experience.

"Experience plus trust are the keys," Kettl said. "A gap in either can create problems in shaping policy and in leading the armed services."

General Brown had previously served as Commander of Pacific Air Forces, US Air Forces Central Command, and as Chief of Staff of the Air Force, with more than 3,100 flight hours as a command pilot. The four-star general and former fighter pilot was also the first African American to lead a branch of the US Armed Forces.

Mark Cancian, a retired colonel and senior adviser with the CSIS Defense and Security Department, said Caine may be missing important qualifications: he was a three star general and did not serve at the highest levels before retiring, unlike Brown who was Chief of Staff of the Air Force before being promoted to Chairman of Joint Chiefs of Staff. However, based on regulations, Caine could still hold this position legally if the president signs a waiver.

"It's not like Caine is a junior person, but that step to four star is a big one," said Cancian, "He will need to get up to speed and change his perspective from what it had been before, which was more Air Force focused, and that will be an extra challenge though not impossible."

Cancian said the only time he could think someone coming out of retirement to be appointed chairman of Joint Chiefs would be when John F. Kennedy appointed General Maxwell Taylor to the position in 1962. Maxwell, however, was already a four-star general, and his predecessor was not fired.

"The US military is ultimately under civilian control and the President is commander in chief of the military," said Jonathan Adler, a law professor at Case Western Reserve University School of Law, "So while it is not common to fire the Chairman of the Joint Chiefs, the president has that authority."

Who is Dan Caine?

Caine graduated from the Virginia Military Institute in 1990 with a degree in economics and later earned a master’s in air warfare from the American Military University.

He would go on to log over 2,800 hours flying the F-16 fighter jet, including over 150 combat hours, and later served as an associate director for military affairs at the CIA.

Trump has long expressed admiration for Caine. In a 2019 speech to the Conservative Political Action Conference, he recalled meeting Caine in Iraq, when Caine told him that the Islamic State group could be destroyed in as little as a week instead of years.

"'We're only hitting them from a temporary base in Syria,'" Trump said Caine told him. '"But if you gave us permission, we could hit them from the back, from the side, from all over — from the base that you're right on, right now, sir. They won't know what the hell hit them.'"

"General 'Razin' Caine was — he's some general. He's a real general, not a television general," Trump added at an appearance in Miami last Wednesday, where he criticized the current military leadership.

Announcing his nomination on Truth Social, Trump described Caine as "an accomplished pilot, national security expert, successful entrepreneur, and a 'warfighter' with significant interagency and special operations experience." Trump also credited Caine for the "complete annihilation" of ISIS during his first term.

Shield Capital announced in January that Caine had joined its team as a "venture partner."

In a press release at the time, the tech-focused firm described Caine as a "distinguished leader" who would bring both military and entrepreneurial experience to the position.

According to his LinkedIn profile, Caine has held a number of private sector roles, including cofounding Texas-based private airline RISE Air.