Air Force Gen. Dan “Razin” Caine, the new chairman of the Joint Chiefs of Staff, had to make life-and-death decisions on the very first day of the Global War on Terror.
The Senate confirmed Caine on Friday morning as the president’s top military advisor. He replaces Air Force Gen. Charles Q. “CQ” Brown Jr., whom President Donald Trump fired in February.
On Sept. 11, 2001, Caine was assigned to the Washington, D.C. Air National Guard’s 121st Fighter Squadron when his unit got orders directly from the White House to scramble its jets into the air above the capital region, according to a 2023 CIA news release. Caine served as mission commander for his flight, during which he and his pilots were authorized to shoot down any planes that posed a threat.
“To have the decision to shoot down an airliner resting solely on a bunch of young folks in a combat air patrol — that had never happened before,” Caine recalled in the 2023 news release. “I remember telling the wingman that I was going to fly with that day, ‘Don’t shoot anybody. I’ll make the decision,’ because I was very mindful that if we made a mistake or if we got it wrong or if we missed somebody and we did not shoot, the consequences of that could be catastrophic, not only for the people on the ground, but for the country as a whole.”
Caine is coming back to active duty to serve as chairman of the Joint Chiefs of Staff after retiring as a three-star general officer. He is now a four-star general, according to his updated Air Force biography, and a spokesperson for the Air Force, as well as a spokesperson Chairman of the Joint Chiefs of Staff.
A ‘no-notice’ combat mission
Retired Air Force Lt. Gen. Marc H. Sasseville was one of the F-16 pilots flying in Caine’s unit during the Sept. 11, 2001 terrorist attacks. He recalled how Caine, the senior F-16 pilot that day, told his wingman not to shoot unless Caine gave permission first.
“’Weapons free,’ which was the rule of engagement at the time, essentially pushes the authority to shoot to the lowest level, which is the pilot,” Sasseville told Task & Purpose. “‘Razin’ wasn’t comfortable, and rightly so, I think, of completely letting that decision rest with his wingman, and he wanted to take some of the decision space for himself, to not only make sure that it was a good call but also to help preserve the wingman’s mental space in the aftermath if we were going down that road.”
If an Air Force fighter pilot had been forced to shoot down a passenger liner, it would have likely come down in a populated area, Sasseville said.
“Even if you rammed the airplane, like was my plan, or you shot it down, you’re still going to live with the trauma of killing a whole bunch of civilians — certainly on the airplane, and maybe even on the ground, depending upon where it goes down,” Sasseville said. “And in D.C., there are going to be people hurt. So, he wanted to be a part of that conversation.”
Prior to taking off, Caine made several key decisions, ordering the squadron’s weapons troops to arm the fighters with live missiles that were regularly kept in storage, Sasseveille said. Amid the chaos, Caine also had to bridge the communication gap between military and civilian officials, who use different terminology to track incoming aircraft.
“His attitude was fearless,” Sasseville said. “He knew what needed to be done, and he jumped right in it. He immediately seized the gravity of the situation, immediately understood the strategic impacts as the airplanes were plowing into the Twin Towers and one into the Pentagon. No hesitation. It felt to me like combat. I think it probably felt the same thing to him: A no-notice combat mission. I’m super proud of him and the way he responded and the way he brought it all together.”
Ultimately, the Air Force did not have to shoot down any passenger jets that day. The terrorist-controlled planes found their targets in Washington D.C. and New York and terrorist onboard United Airlines Flight 93 intentionally crashed it over Pennsylvania when passengers onboard attempted to regain control of the aircraft.
“Not a day goes by that I don’t at some point in the day find a reason to think about the passengers of Flight 93,” Caine said in the CIA news release. “When you talk about courage and you talk about America fighting back more than 20 years ago, that image and example of American courage sticks with me. They knew what was going on, and yet they still had the fortitude to go forward in that airplane, knowing three other airplanes had been hijacked.”
From fighter pilot to top adivsor
A former F-16 pilot and Distinguished Flying Cross recipient, Caine’s most recent assignment was serving as Associate Director for Military Affairs at the Central Intelligence Agency from 2021 to 2024. He was also a part-time member of the National Guard and “a serial entrepreneur and investor” from 2009 to 2016, according to his official Air Force biography.
During his April 1 confirmation hearing, several lawmakers asked Caine if he would provide his best military advice to Trump, even if it meant telling the president things he didn’t want to hear.
Caine vowed to senators that he would “always speak truth to power” by providing his best military advice to the president, secretary of defense, and other top administration officials.
He also said that during the four years he was a cadet at Virginia Military Institute, his dorm room overlooked a statue of Army Gen. George C. Marshall Jr., who served as the Army chief of staff during World War II.
“If I failed to provide my candid advice to the secretary, or the [National Security Council], or the president, I think Gen. Marshall would climb out of his grave and hunt me down,” Caine said at the time.
Retired Air Force Gen. David Goldfein, who served as the service’s chief of staff from 2016 to 2020, said he can personally attest that Caine can give bad news to his superiors.
“I can tell you that he did it for me as chief,” Goldfein told Task & Purpose. “Obviously, I went to him on classified programs and especially those that were key to current operations. I always found him to be able to speak truth to power — no resistance, no hesitance.”
Goldfein said he also observed Caine speak candidly with former CIA Director William Burns.
“That’s part of his credibility, that you know when he tells you something that you can count on it, that he’s done the research, that he’s looked at it from all different sides, and he is coming to you with the best possible advice he can give you,” Goldfein said.
Goldfein says he worked with Caine throughout his Air Force career, going back to when they flew F-16s together, and he said that Caine’s experience in the special operations community has given him a deep appreciation of each military branch.
“He cares deeply about the young enlisted, and he doesn’t necessarily care so much what the uniform is,” Goldfein said. “So, the soldiers and sailors and Marines out there can expect him to be just as big an advocate for them as the airmen around him.”
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