U.S. Air Force Lt. Gen. Dan Caine ’90, then-Central Intelligence Agency associate director for military affairs, speaks about global threats and challenges during the Department of Defense and National Guard State Partnership Program 30th Anniversary Conference at National Harbor, Maryland, July 17, 2023.—Photo by Master Sgt. Peter Morrison.
“Lexington is where it all started.” That’s what U.S. Air Force Lt. Gen. Dan Caine ’90, a highly decorated veteran of a 34-year military career and former CIA associate director, has to say about his cadetship, which he considers foundational to his success in both military and civilian ventures. Over the years, Caine has had a front-row seat for many of the nation’s most terrifying and challenging moments. As he moves into the next stage of his career, he credits the Institute and his brother rats for instilling the values and habits of mind and heart that have enabled him to serve the nation at the highest levels.
Caine, who recently retired from the Air Force, is now chairman of the national security advisory board at Voyager and a venture capitalist with several different firms.
The son of an Air Force fighter pilot, Caine grew up as a typical military brat with frequent moves, and by the time he was in high school, he knew he wanted to follow his father into the Air Force. Growing up, Caine heard of the Institute through meeting many alumni, including retired U.S. Air Force Lt. Gen. Lawrence “Larry” Boese ’66, and he knew of Gen. John Jumper ’66, with whom his father served. With VMI’s reputation leading the way, Caine was sure he’d found his school.
A visit wasn’t possible because the family was stationed in Germany at the time, so Caine’s first day on post was the day before matriculation. At that moment, he had the thought many new rats have: “What the heck did I get myself into?”
Soon, Caine knew the answer to that question. “The Rat Line does a great job,” he stated. “It makes us all equal—regardless of your background, your experience, your religion, your race, your creed, your ethnicity, we’re all rats, and it does a great job of bringing people together.”
But Caine’s rat year wasn’t all about straining and sweat parties. He also had a chance to meet Jumper and give him a tour of post, and today, Caine describes that experience as his first exposure to “the power of the network and the power of the alumni and the caring love that they pour back into all of us there in the Corps.”
An economics major, Caine played soccer during his rat year and held rank in the Corps during his 3rd, 2nd, and 1st Class years. Then, after an unfortunate incident with the officer of the day, he had “a chance to march some penalty tours.” After graduation, he headed off to USAF Pilot Training at Sheppard Air Force Base in Wichita Falls, Texas. By summer 1994, he was in Syracuse, New York, where he was assigned to his first F-16 squadron, and in 1999, he was the top graduate from the Air Force Weapons School Instructor Course (aka TOPGUN for the Air Force). He noted that the Air Force school does not have any beach football or volleyball.
Two years later, a brilliantly beautiful September morning at Andrews Air Force Base was shattered by news of a plane crashing into the World Trade Center in New York City. Caine was in a meeting when an enlisted service member burst into the room with the shocking news.
“I got up and went to our squadron sort of recreation room or lounge and remember, like all of us, the picture on the TV of the World Trade Center burning. I was standing there when the second airplane flew into the picture and tragically hit the second tower,” Caine stated. “And we knew right then that the nation was under attack.”
Caine, who was a major at the time, was the airborne mission commander responsible for defending the airspace over the White House on that dreadful and terrifying day. After consultation with the Secret Service, Caine found himself getting ready to fly into a vastly unknown situation.
“I quickly grabbed a wingman, and … we came up with this really quick plan to how we were going to defend the nation’s capital. We got dressed and ran to the airplanes and started flying that morning,” Caine recounted. Airborne, Caine could see a vast plume of black smoke rising from the Pentagon, which had been hit by American Airlines Flight 77 less than an hour previously.
In speaking of 9/11, though, Caine is quick to stress he was not a hero of any kind; rather, he was simply doing the job he’d been trained to do. The heroes, he said, were elsewhere. “The passengers of Flight 93, the firefighters in New York, the firefighters in Washington, the first responders in the city. … They showed us all how quickly America responds to things like that,” he continued. “They showed us all the gift of a good example. They gave us all what right looks like.”
When Caine landed his F-16 at Andrews late that afternoon after a 6-hour mission, he found a world diametrically different from what it had been that morning. “Everything had changed, and frankly, for me and my squadron mates, it never went back to normal, even to this day.”
“When I look at the values and virtues that VMI taught us, it’s always given us and me a center point on what right looks like.”
U.S. Air Force Lt. Gen. Dan Caine ’90
For Caine, the post-9/11 world meant packing his bags quickly. He deployed first to Afghanistan and then to Iraq, where, in 2003, he joined a team hunting for Scud missiles in the western deserts of that nation. Caine achieved yet another milestone 2 years later when he became the first VMI alumnus to be selected as a White House Fellow.
Begun by President Lyndon Johnson in 1964, the White House Fellows program brings promising young Americans early in their careers to the highest levels of the federal government to hone their public service and leadership skills. When he began the program in August 2005, Caine was assigned to the U.S. Department of Agriculture, and his first day on the job was the day Hurricane Katrina hit.
Caine would go on to write the USDA’s Hurricane Katrina lessons learned report and contribute to the president’s Hurricane Katrina lessons learned report. In addition, that very eventful and impactful year included Caine leading the entire federal government’s response to the H5N1 avian flu outbreak. Remaining in Washington, Caine then spent a year-and-a-half on the White House staff, where he was a counterterrorism policy director and strategist and helped to write the President’s National Strategy for Homeland Security.
After all that, Caine chose to step back and reassess. “I think as leaders, if we’re lucky, we work through a series of rewirings over the course of our careers,” he stated, “and if we’re lucky enough to have been given insights and understanding … we can go forward and have a positive impact on society and America. The gifts that the fellowship gave me—insights on how to get things done in Washington, how to run very large, complex organizations—helped give me the courage, frankly, to actually leave the full-time military, go into the part-time military, in the National Guard, and start businesses.”
For the better part of a decade, Caine was an entrepreneur working in the healthcare, aerospace, and defense sectors while serving his country in the National Guard. By 2016, Caine was a brigadier general, and 2 years later, he was back in the Middle East, this time as deputy commander of special operations in Iraq and Syria. In that capacity, he led the operational team responsible for the defeat of the ISIS caliphate.
In 2019, as a major general, Caine was at the Pentagon at the secretary of defense’s Special Access Program Central Office, which is responsible for the Department of Defense’s Black Programs—secret military projects. In November 2021, he pinned on his third and final star as a lieutenant general and became the CIA’s associate director for military affairs, a position he held until his military retirement at the end of 2024.
“The job was to lead and manage all matters that live between the United States military, other allies’ militaries, and the CIA,” Caine explained. “Our team of military people and CIA people work tirelessly every day to make sure that the best of the CIA and the best of the military are brought together to do the things that the nation needs us to do and make sure that we’re providing exponential outcomes.”
On Dec. 31, 2024, his last planned day in uniform, Caine posted a heartfelt message of thanks to those with whom he’d served on his LinkedIn page and then headed to Arlington National Cemetery to pay tribute to the fallen. Asked if he’d ever foreseen more than three decades in uniform when he commissioned, Caine replied that while he knew he wanted a long military career, he never could have imagined where that choice would take him.
“Could I imagine 9/11 or the White House or the deserts of the Middle East?” he asked. “No. Nor could I have imagined, most importantly, the incredible and amazing leaders and humans, service men and women that I’ve been blessed and lucky to serve with and for. Not in my wildest dreams could I imagine the gifts that I have been given through being around those professionals during my time in service. Service as both a noun and a verb has delivered so much to me. I do really encourage VMI graduates, whether they go in the military or not, to serve. Do something to help your fellow humans. I think it makes us much more grateful humans.”
In November 2024, Caine was the speaker for the Class of 2026 Ring Figure ceremony. In his remarks, Caine urged the cadets to emulate U.S. Army Gen. George C. Marshall, Class of 1901. “When I’ve been deployed—and I have been many, many times—and I did not know what to do, I would look at my class ring and ask myself, ‘What would Marshall do?’” said Caine. “You, as VMI ring wearers, will always turn toward the hard things.”
Looking back on the young man he was coming out of VMI, Caine can see that the Institute set him on an unwavering path to honor and excellence in all he’s undertaken. “[The lessons of VMI] are the foundation of my career,” he stated. “When I look at the values and virtues that VMI taught us, it’s always given us and me a center point on what right looks like. … Along with my classmates, the gifts VMI gave me are immeasurable, not just in the classmates and brother rats I have, but in the experience, the knowledge, the insights, the character, and values that it showed me on what right looks like. It’s been a huge portion of who I am, and I’m forever grateful.”
Editor’s Note: This article was written before Lt. Gen. Caine’s nomination as chairman of the Joint Chiefs of Staff by President Donald Trump.
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