You don't usually see the nation's highest-ranking military officer taking a seven-year break to become a "serial entrepreneur." But then again, Dan Caine lt general—now General Caine—has never exactly followed the standard Pentagon playbook.
By the time 2026 rolled around, Caine was already a household name in defense circles, not just for his "Razin" callsign or his 2,800 hours in an F-16, but for the weird, winding path he took to get to the top. He’s the 22nd Chairman of the Joint Chiefs of Staff. He’s the guy advising the President and the National Security Council. Honestly, if you look at his resume from ten years ago, you might not have guessed he’d be the one sitting in the most important chair at the Pentagon.
From the Cockpit to the Boardroom (and Back)
Most three-star generals spend thirty years climbing a very specific, very rigid ladder. Caine didn't. He was commissioned back in 1990 out of the Virginia Military Institute (VMI), where he spent his time playing soccer and studying economics. He was a distinguished graduate of flight school, but the 90s were a weird time for the Air Force. They were downsizing.
Caine was worried about getting stuck in a desk job, so he did something a bit risky: he went to the Air National Guard.
For years, he was the guy in the 138th Fighter Squadron in Syracuse. He wasn't just a pilot; he was a "weapons guy." If you know anything about the Air Force, the Weapons School is basically their version of Top Gun, but on steroids. He graduated as an "Outstanding Graduate" in 1999. Then 9/11 happened, and everything changed. He was one of the pilots flying combat air patrols over Washington D.C. in the days after the attacks.
The Mid-Career Pivot
Here is where the story gets kinda unusual. Between 2009 and 2016, Caine wasn't on active duty in the way most people think. He was a part-time member of the National Guard.
While most of his peers were grinding away in staff jobs at the Pentagon, Caine was out in the private sector. He founded The Caine Group, an investment firm. He was doing real estate, cyber, and aerospace deals. He even did a stint as the COO of a regional airline in Canada called Rise Air.
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Most military lifers look at a gap like that as a career-killer. In the "up or out" world of the military, leaving the fast track for seven years usually means you've reached your ceiling. But when he came back to active duty in 2016, he didn't just return; he accelerated. He went straight into the world of Special Operations Command (SOCOM) and Joint Special Operations Command (JSOC).
The Rise of Dan Caine Lt General
By 2021, he had earned the rank of Dan Caine lt general and took over as the Associate Director for Military Affairs at the CIA. This is a massive "bridge" role. You’re basically the liaison between the world of spies and the world of soldiers.
It was during this time that he really started to catch the eye of the folks in the White House. He wasn't just a pilot; he was a guy who understood how to scale a business and how to move fast. In early 2025, when the nomination came down for him to become the Chairman of the Joint Chiefs, it sent shockwaves through the "Old Guard."
"New technology is in startup companies and small businesses, not just in existing prime defense contractors."
That’s what he told the Senate Armed Services Committee during his confirmation. He wasn't interested in the 20-year procurement cycles for a new tank or a new jet. He wanted the military to act like the tech companies he used to invest in.
Why "Razin" Caine Matters in 2026
If you’ve been following the news lately, you know about Operation Absolute Resolve. It was a massive, high-stakes mission involving 150 aircraft, including F-35s and B-1 bombers. It was the mission that captured Venezuelan President Nicolás Maduro.
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Caine was the architect.
He and Secretary of Defense Pete Hegseth were the ones in the room monitoring the whole thing. People were obsessing over the grainy videos of the RQ-170 Sentinel drone spotted in Puerto Rico, but the real story was the coordination. Caine’s background in Special Operations—specifically his time in Iraq during the "Counter SCUD" days—gave him a unique perspective on how to hunt high-value targets.
The Business of War
One of the things that makes people uncomfortable about Caine is his deep ties to the venture capital world. Before he put the fourth star on, he was advising firms like Voyager Space and Shield Capital. He’s a partner at Ribbit Capital.
Is it a conflict of interest? Some critics say yes. They worry that a Chairman with venture capital roots will favor the "little guys" he used to work with over established defense giants.
But Caine’s supporters argue that’s exactly why he’s there. The 2026 defense budget is projected to hit $1.5 trillion. That is a staggering amount of money. Caine has been vocal about "streamlining the Pentagon" and cutting the fat. He wants the military to be more like a startup: lean, lethal, and tech-heavy.
A Man of Nuance
It would be easy to paint Caine as a political appointee or a "disruptor," but he's shown a surprising amount of independence. In 2025, when the President decided to federalize the California National Guard to deal with protests in Los Angeles, Caine pushed back. He openly rejected the claim that the country was being "invaded," which was the legal justification for the move.
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It was a risky move for a newly minted Chairman. It showed that while he might have been a "serial entrepreneur," he still carries the weight of his VMI training and his 30+ years of service.
Specific Achievements and Decorations
You don't get to be the top general without a chest full of medals, and Caine has plenty.
- Distinguished Flying Cross: For his heroics in the air.
- Bronze Star (with Oak Leaf Cluster): Earned during his two tours in Iraq.
- Defense Superior Service Medal: For his high-level staff work.
He's logged more than 150 combat hours. He’s flown the T-37, T-38, and, of course, the F-16. He isn't just a "business general." He’s a pilot who has actually been shot at.
Actionable Insights: What You Should Know
Whether you're a defense contractor, a service member, or just someone trying to keep up with the news, the "Caine Era" at the Pentagon marks a major shift. Here is how to navigate it:
- Watch the "Small" Tech: Caine is looking for innovation in startups, not just Lockheed and Boeing. If you're in the tech space, the door to the Pentagon is more open than it’s been in decades.
- Special Ops is the Priority: His background in JSOC and SOCOM means he favors "surgical" strikes and intelligence-led operations over traditional massive troop deployments.
- Expect Policy Friction: Caine isn't a "yes man." His willingness to disagree with the executive branch on the use of the National Guard suggests we might see more tension between the military and the White House in the coming years.
- The CIA-Military Blur: With a former CIA Associate Director at the helm of the Joint Chiefs, expect even more integration between intelligence agencies and active-duty military units.
The story of Dan Caine lt general is still being written, but one thing is certain: the Pentagon won't look the same when he’s done with it. He’s a blend of the old-school warrior and the new-school investor, and in 2026, that’s exactly the kind of leader the U.S. military has decided it needs.