OPINION — “Working in the CIA is a little bit like Fight Club…but the one thing I can say is, you know, they [CIA officers] are just like in our service [the Air Force] and within the [Defense Department] Joint Force. There are world class professionals over there [at CIA] every single day getting after it in ways that we can’t even imagine. And the honor and privilege of serving with each of them is very near and dear to me…And I still feel that way after three years in that job.
“You know, they are the power of the United States. You know if you can get the Department of Defense and the CIA aligned along with the rest of the Intelligence Community to go do the things we need them to do, it’s unlimited. It’s an extremely special place.”
The speaker was retired-Air Force Lt. Gen. Dan “Razin” Caine, during an interview on November 30, a month before he retired from the Air Force after his final assignment as Associate Director for Military Affairs at the CIA. It was also more than two months before Caine was publicly announced as President Trump’s choice for Chairman of the Joint Chiefs of Staff.
Caine’s 96-minute November interview was with John “Rainin” Waters, for the latter’s Afterburn podcast video. It was publicly released January 26, 2025. Waters, like Caine, was a former Air Force F-16 fighter pilot, but the interview went way beyond Caine’s military assignments.
The interview shows a depth and breadth to Caine’s career that’s much beyond what I had read about following Caine’s February 21 nomination, and gives him, I think, a broader background to be qualified for the Joint Chiefs Chairmanship.
More important to me, Caine makes no mention during the interview of his 2018 Iraq meeting with then-President Trump, although Trump refers to it often. Nor does Caine, during this interview, recall Trump’s repeated tale that Caine said he could defeat the ISIS terrorist group “in less than four weeks,” while generals in Washington were telling Trump it would take four years.
In fact, during the entire interview, the name Trump was not mentioned once, although he had just been re-elected President and would re-take the White House Oval Office in less than two months.
For those reasons, I believe Caine’s own words are worth reviewing.
Caine’s road to the nomination
Caine came from a military family. “I grew up as the son of a fighter pilot. This was our family business,” he told Waters. Caine’s father started his military career flying F-4 Phantoms and was ultimately one of the first Air Force pilots to fly the F-16.
“As a kid,” he said, “I felt like this was something that I really, really, really wanted to do, was fly jets in the Air Force, and after… graduating from Hahn High School where my dad was a squad commander in the 496th Tact Fighter Squadron, I went to college in Virginia [Virginia Military Institute], did ROTC and then ended up being lucky enough, very lucky based on my very marginal GPA, to go to pilot training in Texas.”
It was 1990, and Caine won a spot in the Euro-NATO undergraduate pilot training program. Before completing pilot training, though, there were Air Force cutbacks, and Caine worried that he might become a “banked pilot” — one sent to a non-flying job as the Air Force downsized.
He wrote to some 85 Air Force Reserve and National Guard units around the country, looking for an open slot for an F-16 pilot. “Ultimately the 174th Fighter Wing, the Syracuse Air National Guard had had a guy or gal, I don’t remember, not make it,” Caine said, “and had an opening for a JO (Junior Officer) and took a huge risk on me and hired me at the end of pilot training to come to Syracuse [in 1994] as a young F-16 pilot. I still can’t believe they took a risk on me.”
He went from the Syracuse Air National Guard unit and transferred in 1998 to a Washington, D.C. Air National Guard unit stationed at Andrews Air Force Base, Maryland.
9/11
At the time of the September 11, 2001 terrorist attacks, Caine was a Flight Commander/Chief of Weapons and Tactics for the Air Guard. Shortly after a second hijacked airliner hit the second tower of the World Trade Center, Caine and his colleagues received orders to protect the skies above Washington.
In a transcript released by the CIA, Caine recalled, “Shortly thereafter, the phone rang. It was the White House. At the other end of the line, we could hear the Vice President of the United States telling us to get everything we could airborne and to scramble because ‘America’s under attack.’”
Caine continued, “We grabbed the nearest wingman, myself, and one other flight lead, and four of us ran to a briefing room where we came up with a really quick plan on how we were going to defend Washington, D.C. from further attacks. By that time, my wing commander, Brigadier General Dave Wherley, had come in holding a piece of paper. It was a faxed copy of the Rules of Engagement.
“He [Wherley] said, ‘Dan, I don’t know what’s going to happen out there. I don’t know what you’re going to see. And I expect you’re going to have to make some very difficult decisions. Bur what I want you to know is you’re going to do the right thing. I trust you. And no matter what, I have your back.’”
Caine recalled that his unit intercepted about a dozen different aircraft that day, signaling the pilots to change course to clear the skies around D.C.
“I remember telling the wingman that I was going to fly with that day,” Caine said in the CIA release, ‘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.”
The Iraq war
Shortly after 9/11, Caine was sent to Kuwait as the F-16 Mission Commander/Chief of Group Weapons and Tactics, for an Air Expeditionary Group that was doing interdiction and other missions. After four months, he was brought back to Central Command headquarters, MacDill Air Force Base, Florida, in February 2002 for a new and important mission.
He became what was called, “Counter SCUD Project Officer,” which referred to a secret U.S. planning group preparing ways to eliminate the SCUD short-range ballistic missiles in the hands of Iraq President Saddam Hussein. It was more than a year before the 2003 U.S. invasion of Iraq.
As Caine put it during the Afterburn podcast interview, “That’s really the beginning of what changed the heading and direction of my career.”
Caine described how in early 2002, before the Iraq invasion, he was part of a team that included American, British and Australian special forces that put together a secret Pentagon plan to destroy Saddam’s SCUDs. Then they moved to Nellis Air Force Base in Nevada where, at night, they practiced executing the plan.
“We ultimately executed this on the first night of the war,” Caine said, “infiltrating all the special forces folks into where they needed to be to execute this plan. And I think from that readiness, from that approach…there’s no more SCUDs out there.”
In recalling this operation, Caine did not leave out the human side. He said, “There became a very tight emotional connection between those of us in the jets and those cats [troops] on the ground. And I think when I look back on it, of course, the strategic objective of no-SCUD-shot was what we wanted to do. But we had over 100 tics (troops in contact) in that period of time, many of them danger close, and we never lost a single person on the ground.”
Caine said the lessons from his Iraq experience and the current Ukraine fighting – with the introduction of mass drone use – should be that “our ability as a war-fighting nation to pivot at speed, to stay ahead of these emerging technologies is going to be really important in the future. You know, there’s a whole bunch of things that we need to do. We need to do better as a joint force and as a Department of Defense along the lines of acquisition reform so that we can make sure that those young…[soldiers and non-commissioned officers] have the kit and capability that they need.”
Caine said the U.S. holds an advantage in its innovative approach.
“I’m encouraged by the nation’s entrepreneurial community,” he said. “I mean, there are great young entrepreneurs, both in the service and out of the service, who are thinking about these things and ahead of it.”
He added, “We have an advantage as a nation is in the power of our forces to think about hard things and come up with solutions…In the joint SOF [Special Operations Forces] community, most of the smart people are not the O’s [officers], it’s the E’s [enlisted men]. And it’s really the NCO cadre. And when I look at combat capability development within the SOCOM enterprise, it’s the NCOs who are figuring these things out and bundling things together in new and novel ways to try to create dilemmas and or disruption for these things that we’re talking about.”
In 2003, Caine was assigned as Chief of Weapons and Current Operations at the Air National Guard and Reserve Test Center, located at Tucson Air National Guard Base, Arizona. He described those two years as an “opportunity to serve with…epically world class tacticians, leaders, thinkers, humans,” who he says were “very special to me, especially at that time in my career.”
He said, “We had this incredible group of folks that were unbelievably committed to getting combat capability to the field right now, from the operational test pilots to the flight test engineers even to the contractors.”
What followed was among Caine’s more interesting assignments, and one he failed to get first time he tried. It was to spend a year, beginning in August 2005, as a White House fellow – a position another future Joint Chiefs Chair, Colin Powell, had held in 1972. The program, Caine said, was “designed to take leaders who were early in their career, take them from either the private sector or the military, bring them to Washington with the objective of giving them insights into how senior leaders make decisions at the cabinet or presidential level.”
After 14 or 15 interviews in the Washington area, Caine said he was picked to be one of the fellows –but then assigned to the Department of Agriculture.
As Caine described it, “I was super uncertain about what the heck would I do at the U.S. Department of Agriculture…[but] the first day of our White House Fellowship, Hurricane Katrina made landfall and…our class was instantly involved with the response and the recovery.”
As Caine described it, then-Agriculture Secretary Mike Johanns [later a U.S. Senator from Nebraska] took Caine to the Eisenhower Executive Office Building next to the White House, where they attended a “big cabinet-level, synchronization meeting.”
Back at Agriculture, Caine said he learned that “USDA does way more than just agriculture…wifi in rural areas, they do aid, they do food safety and security. They do all kinds of things that would just blow your mind.”
In the response phase, Caine said, “We were really working on how do we lash up the department with the other agency, federal, state, local, and tribal entities that were responding.” When President George W. Bush ordered a lessons-learned assessment after Katrina, Caine said, “I was tagged by the Secretary [Johanns] to lead USDA’s debrief,” which led to him writing the report for the White House.
During this time, Caine said he got close to the White House Homeland Security Council, “and that’s ultimately how I ended up going to the White House after my fellowship.” From October 2006 to January 2008, Caine served as Policy Director for Counterterrorism and Strategy for the White House Homeland Security Council.
He described the job as running “the interagency process…the way the U.S. makes policy decisions.…You have a particular issue or policy that needs to be thought about, know, what is America’s policy against blank going to be? And you’ll bring the relevant stakeholders together to talk about all the policy considerations.”
Caine went on to describe the traditional process, “When it’s time for a decision to be made, we’ll take that to the deputy secretaries of the departments and agencies…and then if the deputies can agree, then that policy is issued to the interagency and we go forward and do it. If they can’t, then we may take it to what’s called a principles committee or a National Security Council meeting. And that’s where the actual cabinet secretaries or senior White House leaders come together, or in some cases the president. And they’ll banter back and forth on. a particular issue and ultimately either reach conclusion or have the president make a decision.”
I’ve used Caine’s descriptions of his positive experiences with the federal bureaucracy, including the CIA, and his description of the White House decision-making when it comes to national security, because that does not seem to be the way President Trump and his top aides do or see things.
For me, that raises the question: How long can Caine last in a position where Trump has fired at least four incumbent Joint Chiefs Chairmen in the four years, one month, plus two weeks that he has been President?
By the way, I don’t believe the stories that Trump has told about Caine telling Trump “I love you” and putting on a MAGA hat when they met in Iraq in 2018. It was Trump who said, at the CPAC conference, who said, “I love you,” after mentioning Caine; and Trump then described a sergeant at that 2018 meeting who put on the MAGA hat, which Caine has since denied doing.
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