The moment was quickly overshadowed by other events—first an airline disaster in India, then the outbreak of war between Israel and Iran—but it was nevertheless noteworthy. On June 11, General Dan Caine, the chairman of the Joint Chiefs of Staff, appeared before a congressional appropriations committee alongside his boss, Defense Secretary Pete Hegseth. Caine, personally selected by President Donald Trump in February and on the job for barely two months, had been keeping a very low profile. Until recently, it was impossible to find on the internet where and when he was born. (Elmira, New York, August 10, 1968.) Staying out of public view was a wise move, given this president’s fractious relationship with America’s military leaders. Trump has said he expects loyalty from “his” generals and casts them aside when they displease him.
Caine’s immediate predecessor, General Charles Q. Brown, was fired just 16 months into his four-year term for the apparent sin of having been appointed by President Biden. Brown, a decorated fighter pilot who is Black, was cast as both a product and an author of “woke” policies at the Pentagon, policies he neither controlled nor would have been free to ignore. Trump’s loathing of General Mark Milley, who preceded Brown, is widely known and ongoing; his official portrait in the Pentagon has been taken down, and earlier this year Hegseth claimed that Milley is under investigation. Brown and Milley are just two of Trump’s discarded and insulted military leaders. On Truth Social, the president has called H. R. McMaster, the former national security adviser, “WEAK AND TOTALLY INEFFECTIVE” and former Chief of Staff John Kelly “a LOWLIFE” and “a bad General”; Trump has also referred to former Defense Secretary James Mattis as “the world’s most overrated general.”
But now Caine was before the cameras. He faced a public session of a Senate subcommittee, and he was asked some questions that put him on the spot. One was from Democratic Senator Brian Schatz of Hawaii, who asked about the immigration protests in Los Angeles. The administration had sent the National Guard and the Marines to the city to meet what it said was a “foreign invasion”—a claim being used to justify the legality of deploying American troops on American soil. Schatz asked: Did General Caine believe the country was being invaded?
Caine replied, “Sir, thanks for your question. At this point in time, I don’t see any foreign, state-sponsored folks invading.”
A second question came from Republican Senator and Trump confidante Lindsey Graham, who asked about Vladimir Putin’s territorial objectives. At the time, the Trump administration argued that Putin has no larger ambitions in Eastern Europe and that Russia will be satisfied with consolidating its gains in Ukraine. Graham asked: Did General Caine believe that Putin was prepared to stop in Ukraine?
“I don’t believe he is, sir,” Caine replied.
Hegseth, seated next to Caine, and speaking at far greater length, was at pains to present a different view, but it was obvious what the headline was going to be. Within minutes, the CNN crawl read: “Trump’s Top General Just Undercut His ‘Invasion’ Claims.” The Washington Post headline read: “Trump’s Top General Contradicts His Assessment of Putin, L.A. Unrest.” In just a few words, Caine had very publicly called into question two of Donald Trump’s favorite assertions.
Trump seems to have been drawn to Air Force General Dan “Razin” Caine at least in part because he loved his nickname—which happens to be Caine’s F-16 call sign. In February, the president elevated Caine, a retired three-star general, to the nation’s highest military office. It was a typically unorthodox decision: Caine was promoted over the heads of all 38 active-duty four-star generals and admirals. He assumed his duties as the military faced pressure from the president for the use of federal troops as a domestic police force; soon, the president would order U.S. bombers and submarines to attack nuclear facilities in Iran.
Trump has at least twice told the story of how he first encountered the former fighter pilot on a visit to the al-Asad Air Base, in western Iraq, in late December 2018. The president had gone, as he put it, “to meet the generals” and “find out why we’re not defeating ISIS.”
The Pentagon’s top command and his advisers were telling him that the effort would take many more months, possibly even years. So Trump was delighted when, in his telling, a frontline, lower-ranking officer at al-Asad told him that if more American power were unleashed, the job could be done in a week.
“You’re the man I’m looking for,” the president said he told the officer. He related the story in his 2019 speech to the Conservative Political Action Conference (CPAC):
I said, “What’s your name?”
“Sir, my name is Razin.”
“What the hell kind of a name?” I said. “Raisin, like the fruit?”
He goes, “Yes, sir, Razin.”
“What’s your last name?”
“Caine. Razin Caine.”
I said, “You gotta be kidding me.” It’s true!
Still smitten six years later, Trump embellished the story in another CPAC address. He related that someone—widely and wrongly interpreted as Caine—had donned a MAGA hat in that meeting, professed his love for Trump, and vowed to “kill” for him. Trump has no compunction about using the military as a backdrop for partisan purposes, but by long tradition the Pentagon stays out of politics. As Caine diplomatically put it during his Senate confirmation hearing in April, when reminded of Trump’s account, “I think the president was actually talking about somebody else.”
Trump may have misremembered, but he didn’t forget. He had found his man, a seeming hell-raiser after his own heart. In February, weeks into his second term and six years after that meeting at al-Asad, Trump nominated Caine to head the Joint Chiefs. Caine is the first man chosen for the job who was outranked by all the other service chiefs. Multiple senators saluted Brown for his service during the confirmation hearing for Caine, who in turn thanked the general for his “more than 40 years of selfless service to our nation.” Caine was confirmed, but 25 senators, all Democrats, voted against him, less out of objection to Caine than concern about Trump’s handling of the appointment.
As tickled as Trump was about Caine’s call sign, it’s not clear what he thought it conveyed. Fighter pilots are given call signs with multiple meanings, often comical. “Razin” does suggest that Caine is given to bucking rank and shaking things up, precisely the qualities that delight Trump. But call signs are often ironic—like calling a skinny kid “Fats.” Caine is known as a team-oriented officer with a deep respect for the chain of command. He might be the last person in the ranks to raise hell. And the word with the dropped g is, in any case, not raising but razing. It evokes Caine’s skill spearheading air assaults as a fighter pilot.
Heather Penney, a retired Air Force major who flew F-16s with Caine, put it this way when I spoke with her: “Making an offensive counter air push with Razin in the lead—man, everything died in front of us. He was just so good.”
Caine was awarded a fourth star just before he was sworn in as chairman. This was pro forma. Traditionally, chairmen have previously held a “combatant command” or led a branch of the military, the usual criteria for a fourth star. The chairman of the Joint Chiefs commands no troops; he has others around him—chiefs of the Army, Navy, Marine Corps, Air Force, Space Force, and National Guard—who do. But Caine’s background might actually make him better suited for the top job today than many of his peers. Particularly since the U.S. withdrawal from Afghanistan and Iraq, American military action has primarily employed three sectors: air power, covert special ops, and intelligence. The attacks against Iranian nuclear sites in June certainly involved two of these and likely all of them. Here Caine has more direct experience than most four-stars. He has been providing air cover for covert or “dark” units on and off since helping to hunt Scud missiles in Iraq prior to the 2003 invasion. And he recently concluded three years of service as associate director for military affairs at the CIA, commanding that agency’s secret missions.
His climb through the ranks was always unorthodox. He left active duty to become a White House fellow in 2005–06, working for the Department of Agriculture, followed by a stint at the Homeland Security Council. Through the years that followed, he moved in and out of full-time station, partnering in business ventures while serving part-time with the National Guard and receiving steady promotions by the Air Force (Guard pilots have dual status). He is the first Air Guardsman ever to rise to chairman of the Joint Chiefs. Prior to his selection, he had retired at age 56—he called it a “graduation,” not a retirement—to become a partner in a venture-capital investment firm. By all accounts, Caine had no idea that he would soon be back in uniform, much less in the job he now holds.
The president has made many startling top-level appointments, often of people with minimal credentials and with values at sharp odds with the agencies they lead. Some of the people he has chosen seem keen mostly on the performative aspects of the job. (Hegseth is a former co-host of the weekend edition of Fox & Friends.) Caine does not fit this mold, and his selection was met with relief from the career military. He is known to be apolitical, and is genuinely liked. Where Trump is boisterous and self-aggrandizing, Caine is retiring and reflexively self-deprecating. The chairman is openly religious and prays over important decisions.
The role of chairman of the Joint Chiefs is defined by Chapter 5 of Title 10 of the U.S. Code. The chairman is strictly an “adviser.” He (there has never been a woman in the role) does not make decisions or command troops. When the chairman transmits orders to combatant commanders, he does so in the name of the president and the secretary of defense. He collects information, analyzes it, and develops recommendations for the president, the defense secretary, the National Security Council, and, importantly, Congress—which explains Caine’s contradiction of Trump in his committee testimony.
The statute makes clear that the chairman is independent. No matter how Trump has presented Caine, the general is not a political appointee or a member of the administration. When a president formally addresses Congress, his Cabinet is seated to his left in chairs that have their names engraved on the back. The chairman of the Joint Chiefs is not among them. He is seated with the other service chiefs to the president’s right, by the Supreme Court justices. His advice is meant to reflect the judgment of the military alone, heedless of political or partisan considerations. Caine will find that it is hard to give advice to a man who feels he already knows best and prefers not to be contradicted.
Top generals from Douglas MacArthur to George C. Marshall—though neither of them was a Joint Chiefs chairman—have found themselves snared in political disputes, sometimes of their own making. During Trump’s first term, Mark Milley was accused of both siding with the president and undercutting him. Merely disagreeing or correcting Trump is enough for the president to accuse someone of disloyalty. Telling superiors what they do not wish to hear is part of a senior military officer’s job—and one reason why Trump has rid himself of multiple generals he has been close to. Will Caine have to remind Trump that using the military against American citizens is illegal, as is using the military to arrest and deport immigrants? Trump may not want to hear that concern for civilians can impede drone strikes abroad, or that invading Greenland or Panama would violate international law. Caine told reporters it was “way too early” to assess the impact of the U.S. strike on Iran’s nuclear facilities; Trump almost certainly did not want to hear this. The conflict with Iran will evolve in ways that cannot be foreseen, and Caine may soon be presenting Trump with complex, delicate questions that disturb his fondness for simplicity.
It would be hard to list all the points of potential friction in store for Caine. Trump is given to flashy displays and fancy and expensive new armaments—a new F-47 fighter jet (the “47” honors, in part, his second presidency), a “Golden Dome” of anti-missile defense for the entire country—this at a time when the military’s industrial base is incapable of meeting basic demand for munitions. Caine’s hasty elevation may also put him in the awkward position of having to deal with service chiefs and combatant commanders whom he now outranks. There is a danger, from both the Pentagon and the White House, that he will find himself sidelined. And if Trump doesn’t like what he hears from his top military adviser, he can always just stop listening—or send Caine to join Brown, Milley, Mattis, and Kelly in private life.
Dan Caine might not meet some of the historic criteria for success in a Trump administration, but he does look the part—a big consideration for this president. One of Trump’s highest compliments is to describe someone as “right out of central casting,” a phrase he has used to describe Caine: a white, middle-aged male, hair flecked with gray, chest pinned with rows of service ribbons. He is fit and small, seemingly made for the snug cockpit of a fighter jet. He has dark eyes, a broad forehead, a long, prominent nose, and thin lips that curl slightly at the ends, giving him a naturally mirthful expression. He is poised, careful, and deliberate, with an arrestingly direct gaze. His manner is so deferential that, while genuine, it might lull others into underestimating him. He is generally reluctant to talk about himself, but when he gets going he is a skilled and humorous storyteller, usually making himself the butt of the joke. From his youth, he appears to have been without ambition for rank or status—among other things, his occasional detours into civilian life would usually be missteps for an officer bent on promotion.
In relating the major jumps in his career, he insists on his lack of distinction and expresses amazement at his luck.
About his college years: a “very marginal GPA,” Caine said last year on a podcast called Afterburn, aimed at the fighter-pilot community.
About his first attempt to obtain a White House fellowship: “Didn’t even get an interview because I was such a marginal applicant.”
As a man who has built his career controlling powerful, complex machines, Caine has a curious way of referring to people: not as men or women or even persons, but as “humans.” His former weapons instructor is “a legendary human.” A training exercise had “world-class humans in it.” The colleagues he worked with at a National Guard test center were “world-class tacticians, leaders, thinkers, humans.”
And as warm a human as he appears, Caine can also lapse into dense pilot-speak. Here’s how he described an early special-ops planning session: “We literally on a whiteboard sketched out what the first-ever data-link enabled, time-sensitive targeting structure might be, from the link CONOPS to roughly how we would task in a portion of air power that was set up in an air-tasking order.”
Caine wanted more than anything to be a fighter pilot. He spent his childhood on American air bases around the world, watching and feeling those sleek, powerful machines thunder overhead. Caine’s father, retired Colonel Steve “Cobber” Caine, had been up there, flying the F-4 fighter in the Vietnam War, and later commanding a squadron of F-16s. He wanted one for himself. In 1990, fresh out of the Virginia Military Institute’s ROTC program, Second Lieutenant Caine was accepted for Air Force pilot training, a notoriously selective program. He learned to fly the first-level trainer T-37, a two-seat subsonic jet called “Tweety Bird,” or the “Mighty Tweet,” to distinguish it from the more challenging next-level trainer, the supersonic T-38 nicknamed “Talon.” Many trainees don’t get that far; they are routed to the Air Force’s giant fleet of transports, tankers, and reconnaissance aircraft. Caine had the skills to go all the way.
But many of the top pilots in Caine’s training class, even if they were moved up to the T-38, would never fly fighters. After Desert Storm, the U.S. military was downsizing. The Air Force had more pilots than planes. Caine foresaw that he would likely be “banked,” or held in reserve. He would earn his wings only to be given an administrative post as, say, a communications specialist or finance officer at a distant Air Force base. He would pilot a desk. Eventually, as opportunities arose, he might get an airplane, but it was just as likely that he wouldn’t.
Coming from an Air Force family, Caine had a better grasp of military topography than most. He knew there were available F-16s with National Guard squadrons around the country. Guard squadrons are under the jurisdiction of states; governors deploy them to respond to natural disasters or to provide a show of force during civil unrest. In the days of Caine’s apprenticeship, they mostly patrolled their state’s airspace, where they were more likely to encounter a UFO than combat, and were summoned for noisy flyovers at ceremonial events. Most Guard pilots were weekend warriors, attending college or holding down civilian jobs. They were available to be mobilized for war, but in this brief illusory moment after the collapse of communism, it seemed possible that America would never again fight one.
For a young Air Force lieutenant on the path to fly fighters, the National Guard was a step down. But these local Guard units had F-16s. Even before finishing his Mighty Tweet training, Caine began pounding out letters and résumés on his typewriter. He sent them to every Guard unit in the country, more than 80 at the time, begging to be taken on, offering to do the most menial scutwork, to be the squadron “snacko,” the one who keeps its off-hours club supplied. He joked about it last year with John “Rain” Waters, a retired F-16 pilot who hosts Afterburn. Caine seemed slightly amazed to recall his youthful desperation and energy, typing away in his off-hours every morning and night. He said he was willing to do anything, even pleading for the snacko post, tongue only partly in cheek: “I’ve trained for this moment. There are 1,964 ounces of beer in a U.S. keg. I will never run out of popcorn.”
He used his leaves to take long road trips, pleading his case in person to every Guard unit that responded. He finally scored with the 174th Attack Wing, in Syracuse, New York, which had a last-minute opening and agreed to bring him on as an F-16 pilot. “I still can’t believe they took a risk on me,” Caine recalled on the podcast. One problem: He committed to Syracuse before he had completed his Air Force training, which, at the time, was like signing with a Triple-A ball club in Scranton while still in camp with the New York Yankees. He would need permission from his wing commander to leave active duty. A move like this was simply not done. The Air Force had invested a great deal of time and money in him, had plucked him from hundreds of wannabe fighter jocks, and it expected him to serve for at least 20 years, whether he was flying or not. Wing commanders jealously guarded the skilled pilots they had in reserve; they had quotas to keep. Now here was Lieutenant Caine, not even fully hatched, asking permission to leave. When he presented his wing commander with the request, Caine remembered, “He lost his mind and threw me out of the office. He would not sign my piece of paper and told me that I was a quitter.”
He kept trying, and eventually his commander caved. Caine is still not sure why. He considers it a lasting stroke of pure luck. The path he took is more common today, at least in part because of his example, but he finished training with what felt like a firm kick in the ass. It only hurt until he settled into the sheepskin seat of his first F-16.
It is a beautiful machine, and a joy to fly—relatively small and enormously powerful, with short swept-back wings and a tall tail fin. In flight it is so sensitive to a pilot’s hand that, as Heather Penney observed, “You think it, and the jet does it.” Despite this ease of control, pilots exit the aircraft after a flight exhausted and drenched with sweat. “Your brain has to be just miles in front of where the aircraft is,” Penney explained, “because of the speed at which you’re going and the closure rates of the tactics.”
Up there at 50,000 feet, inside the frameless bubble canopy, pilots can feel like they own the world. The sky above is dark blue, the bottom of space, and below is a vista so vast that pilots can see the curvature of the Earth. Time stretches as the planet shrinks. Traveling at the jet’s top speed, Mach 2—more than 1,500 mph—a pilot in Washington, D.C., could get on the phone at noon, make a lunch date for noon in Texas, and, with the time difference, arrive early.
By 2001, Caine had completed Weapons School—the Air Force’s equivalent of the Navy’s Top Gun program—at Nellis Air Force Base, in Nevada, and was flying with the National Guard’s 121st Fighter Squadron out of Andrews Air Force Base, just outside D.C. He was there on September 11, when hijacked commercial airliners flew into the World Trade Center towers, in Manhattan, and the Pentagon, in northern Virginia. Pilot Heather Penney’s call sign was “Lucky,” which played on her surname but also, she says, evoked the adage “Better lucky than good.” Women F-16 pilots are rare even today. Thirty-four years ago, she faced unveiled hostility from some of her male colleagues. Caine was not one of them. “Razin has a quiet authority about him that is based on his credibility and his knowledge,” Penney told me. “He was not egoistic. You might imagine that someone with his level of training would have been, but he was incredibly humble.”
That sunny morning in September, the attacks came literally out of the blue. In the first hour, there was no knowing what would happen next. And, in fact, a fourth hijacked airliner, United 93, was now bearing south toward Washington. What was to be done about it? The 121st Fighter Squadron was not one of the Guard’s four designated “alert units” in the country. The missiles the F-16s would have carried weren’t even assembled. Their machine guns were loaded with nonexplosive training rounds. Lieutenant Colonel Marc Sasseville, the squadron’s commander, ordered Caine and his wingman, Brandon Rasmussen, to wait for missiles to be assembled and loaded onto their fighters before taking off. Sasseville chose Penney to fly her plane on his own wing, and the two of them ran to their unarmed jets and took off, bent on intercepting any planes that might enter the capital’s restricted airspace. Their options for stopping one were near suicidal. As Sasseville assessed it, they could shoot their training rounds and pray that they hit a fuel tank and caused a spark to ignite it. If they strafed the cockpit they might hit the hijacker pilot, but the airliner could still be controllable and a threat.
“I really needed to make it stop flying,” he told me. “And the only way to do that was to ram it and break a wing off it; then it would disintegrate in the air. The risk of surviving that, in my estimation, was low, because I’m not aware of anybody who’s ever tried. So my idea was to have one hand on the stick guiding the airplane towards the wing root with the other hand on the ejection handle.”
As it happened, before Sasseville and Penney even took off, United 93’s passengers had attacked their hijackers and sent the plane crashing into the Pennsylvania countryside, killing everyone aboard. But no one in the 121st Fighter Squadron knew that. All four pilots had faced the lasting horror of having to contemplate bringing down a commercial airliner in flight, perhaps suicidally. It hadn’t been necessary, but the scenario became the pilots’ legacy, and made them famous in their community.
In early 2003, before the U.S.-led invasion of Iraq, a secret American air base was established in eastern Jordan. During the first Gulf War, a decade earlier, Iraqi President Saddam Hussein had fired Soviet-designed Scud missiles at Israel. This time around, the plan was to destroy Saddam’s Scuds before the fighting started and Caine, in addition to flying his F-16 on attack missions, was the project officer. To execute it, he had worked closely with the special-ops teams for almost a year.
Lieutenant Colonel Vinnie Savino’s 38th Air Force Rescue Squadron had been one of the first on the ground at the base in eastern Jordan. His unit had 25 airmen to start. After they helped build out the old Jordanian airfield to suit the needs of a continuing U.S. operation, the 38th settled into a hangar at the far end of the flight line. They had a ringside seat as the warplanes began to arrive, screaming down to land and taxiing to the far end of the runway, where the headquarters were. This was the 410th Air Expeditionary Wing, the fliers Savino’s unit would have to go find if they bailed out inside Iraq.
In general, tech sergeants do not mingle with fighter pilots, so Savino was surprised when Dan Caine showed up at his hangar, just to get to know the unit. Then he brought the other pilots in his wing—“guys and gals,” said Savino, approvingly. Together Caine and Savino planned a “monster mash,” a grueling running and training exercise meant to simulate the conditions of a rescue. Savino recalled the kinds of questions he asked Caine and the other pilots.
If you eject and make it to the ground, do you just get up and run?
They discussed the likely terrain, and then the pilots were sent off to run several miles in their gear through land that might resemble it.
What if your co-pilot or wingman is injured?
They practiced emergency first aid.
What kind of weapon will you have?
Pilots carried 9 mm pistols.
What if you have a broken arm? How are you going to cock your weapon?
They were shown how to cock a pistol with their heel.
One day in 2005, Mike Johanns, then the secretary of agriculture, spotted a new face outside his office.
“What do you do here?” Johanns asked a 37-year-old Dan Caine.
“Anything you want, Mr. Secretary.”
Caine, then a lieutenant colonel, had succeeded in winning a White House fellowship on his second try, and was assigned to the USDA, an agency he knew little about and had never expected to join. “Well, come with me,” said Johanns. They were driven in the secretary’s car to the Eisenhower Executive Office Building, built in the French Second Empire style, immediately west of the White House. Caine followed Johanns into an elevator, which quickly filled with famous faces. There was Andy Card, the president’s chief of staff, and Vice President Dick Cheney with his Secret Service agents. “I’m just shrinking into the back of the elevator, hoping that no one will say anything to me,” Caine told Waters in the Afterburn interview, describing his year with the USDA.
The George W. Bush administration was starting to dissect the federal response to Hurricane Katrina, which had devastated New Orleans, killed an estimated 1,800 people, and caused massive flood damage in three southern states. The administration had been widely criticized for its slow response. Now it was going to study what went wrong and how to be better prepared. Caine was given the job of reverse-engineering the USDA’s response to the disaster.
If there is a single trait that defines a good F-16 pilot, it is the ability to monitor and process a dizzying flow of data from a variety of cockpit screens, and to react quickly. Caine was now soliciting data from a department with more than 100,000 employees and eight major divisions. Many functions were in play during a national disaster. He pulled together the information and then briefed his boss. Mike Johanns gave Caine additional responsibility, which generated pushback. Johanns recalled, “I actually had a staff person come to me while Dan was with us and say, ‘You know, Mr. Secretary, you’ve given him so much authority here, and keep in mind that he’s just a White House fellow.’” The staffer pointed out that Caine was very young, very inexperienced, and very temporary. The secretary was unmoved. “He was just so capable,” Johanns told me.
People also tend to trust Caine. “I think the way I would describe it is: If you would’ve talked to the director of the CIA, he would’ve told you that Dan was his guy,” said General Jim Slife, who was fired by Trump as Air Force vice chief of staff this past February, in an interview. “And if you would’ve talked to the chairman of the Joint Chiefs or the secretary of defense, they would tell you that Dan was their guy. It’s just that Dan was able to understand and empathize with each of the parties and communicate in a way that made them understand that he knew what their equities were and he was fighting for their equities. I don’t mean that in any way as a put-down. I mean, I think that’s graduate-level interpersonal skills.”
Trump had an agenda on that trip to Iraq’s al-Asad Air Base in 2018. A sizable American force was still in the area, seven years after U.S. combat operations had officially ended. Trump had announced a week before his visit that he was going to withdraw all of the U.S. forces in Syria and half in Afghanistan. This conflicted with the Pentagon’s advice—doing so would be dangerously premature and betray our allies—and Secretary of Defense Mattis resigned. At that point, the fight was focused on the remnants of ISIS in Syria. There was also the ongoing effort by a variety of factions—often at war with each other—to oust the dictator Bashar al-Assad. The American mission was primarily to assist one of these factions, the Syrian Democratic Forces, which was doing most of the fighting against ISIS on the ground. Knotted up in this were relations with Russia, Iran, Israel, Turkey, and other powers. Trump is notoriously intolerant of complexity. He regards expertise as hidebound thinking. He came looking for a simpler solution.
As a precaution during its approach to al-Asad—an active war zone—Air Force One had turned off its lights. This irritated the president. “We spent $7 trillion in the Middle East and we can’t land a plane with the lights on 20 years later?” he asked a CPAC audience in 2019, prompting laughter and applause. “How bad is it? No, seriously, how bad is it? How bad is it? Seven trillion dollars, and we have to fly in with no lights.” That was his frame of mind when he met with the frontline commanders. Caine was now a general, but one of the lower-ranking ones in attendance. In the years since working in Washington, he had been in and out of active duty, involved with several business start-ups. Now he was deputy to General Paul LaCamera, who headed the Special Operations Joint Task Force. Caine was also, because of his experience as a White House fellow, probably more comfortable addressing a president than others in the room. After describing in that 2019 speech how he had learned Caine’s name, Trump went on to elaborate:
So I have Razin Caine, three other generals, colonels, sergeants … And I said to the generals, “Listen, we got to get out. I want to know why is it going to take two years to knock off 2 or 3 or 4 percent [of ISIS], which is what we had left.”
“It won’t, sir.”
And I said, “Tell me why it won’t.”
“It won’t, sir. If we attack them in a different manner, we can do it much faster.”
“Okay, General Razin Caine, how fast can—”
“Sir, we can have it totally finished in one week.”
I said, “One week? I was told two years.” [Laughter.] “One week?”
“That’s right, sir. We’re only hitting them from a temporary base in Syria. 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.” [Applause.] “They won’t know what the hell hit them, sir.”
And I said, “Why didn’t my other generals tell me that? Why didn’t they tell me that?” I said, “Did you tell them that?”
“Not our place to say it, sir. They come in from Washington, sir. We have to take orders. You’re the first one to ask us our opinion.” [More applause.]
It’s true. It’s true. True. True.
It wasn’t. The set-up was one of Trump’s standard tropes—the commonsense, inspired leader beset by elite nincompoops who plucks a like-minded soul from the lower ranks—and the account was false. Other sources familiar with the meeting, though reluctant to challenge Trump’s account in public, say that Caine did not act or speak the way Trump said he did. He did answer Trump’s questions, but not about the U.S. effort in general. He was presenting a plan of attack for a single ISIS location, which he was confident could be destroyed rapidly. He did not offer an opinion about the overall operation, nor did he imply that the effort was somehow hamstrung by official limitations. Nothing Caine explained to the president differed from what the others in the room understood. And the upshot of the meeting was that the assembled generals, including Caine, persuaded the president that any sudden withdrawal of American troops would be against U.S. interests, a gift to ISIS, and a betrayal of trusted allies. The forces were not withdrawn. Today, seven years later, thousands of American troops are still supporting the effort to destroy what remains of ISIS in Syria.
None of this apparently made a dent in Trump’s memory, or in his impression of Caine. In his 2024 retelling, here were his exact words about that initial encounter with Caine, after he asked for the general’s name.
And he gave me his name.
“What’s your name, sergeant?”
“Yes, sir. I love you, sir. I think you’re great, sir. I’ll kill for you, sir.”
Then he puts on a Make America Great Again hat. You’re not allowed to do that, but they did it. I remember I went into the hangar, and there were a lot of—hundreds of troops. And they’re not supposed to do this, but they all put on the Make America Great Again hat, right? Not supposed to do it. I said, “You’re not supposed to do that. You know that.”
They said, “It’s okay, sir. We don’t care.”
It’s easy to see why reports of these remarks were confused. Trump’s fluid rhetorical style is, perhaps deliberately, tough to pin down. Note the ever-shifting focus: asking for Caine’s name, then a reference to “he,” then to “sergeant,” then to “they,” and then back to “general.” A close reading shows that Trump was not putting the MAGA hat on Caine, but rather on an unnamed sergeant. Still, Trump never clarified the matter, or perhaps never cared to, and after the general’s appointment was announced, Politico’s headline read: “MAGA Hat Drama Could Taint Trump’s Top Military Advisor Pick.” The Daily Beast’s headline read: “Trump Makes MAGA Hat-Wearing ‘Killer’ Chairman of Joint Chiefs.”
When asked about the inaccuracy of Trump’s recollections, White House spokesperson Anna Kelly said in a statement: “General Caine successfully helped President Trump obliterate ISIS in just a few weeks in his first term after Obama had called it a ‘generational threat’ we just have to live with, and then he oversaw one of the most secretive and perfectly successful operations in U.S. history—obliterating Iran’s nuclear facilities.” Caine declined to comment for this story.
All of this landed Dan Caine in a touchy spot. He was both beneficiary and victim of Trump’s story—a story that, to officers of his grade, made him look like a toady, if not a buffoon. But how do you deny and publicly embarrass the president who has just raised you from obscurity to the nation’s highest military office?
This is what Trump does: He creates brands. He has had great success doing it for himself, but the brand Trump created for Caine was a bad fit. The general did what he could to discard it during his confirmation hearings before the Senate Armed Services Committee, in April.
“Let me just start out by asking you about some hyperbole that may have been out there in the press,” said the committee chairman, Senator Roger Wicker of Mississippi. “General Caine, did you wear a MAGA hat in front of the president?”
Caine said simply, “No, sir.”
“Did you wear a MAGA hat at any time?”
“No, sir.”
“Okay, would you like to elaborate on that answer?”
“Sir, for 34 years I’ve upheld my oath of office and my commitment to my commission, and I have never worn any political merchandise.”
Concerned about Trump’s tendency to stretch his authority beyond legal limits, Senator Mark Kelly of Arizona asked, “To whom or what do you swear an oath?”
“Senator, as I have for 34 years, it’s to the Constitution,” Caine said.
He was asked repeatedly if he was willing to tell the president things he didn’t want to hear.
“Senator, I think that’s the most important part of this job,” he told Mike Rounds of South Dakota.
“It ultimately is the whole job,” he told Tommy Tuberville of Alabama.
Since Caine became chairman, there have been air strikes in Yemen and Somalia. American troops remain engaged on the ground in Syria, have continued to supply Ukraine, and are present in large numbers in East Asia and the Middle East. In June, Israel launched attacks on Iran’s nuclear facilities and other targets, leading to an outright state of war—one that the U.S. joined with Operation Midnight Hammer, in which American B-2 bombers dropped the most powerful conventional bombs in the U.S. arsenal on three nuclear sites in Iran. At home, the White House has pushed to use military force against domestic protests—efforts that so far have resulted in a highly publicized presence but no real action. The president and his chairman have lots to talk about.
By all accounts, Caine is giving straight professional advice. He seems to prefer doing so in private, although when called on to comment publicly he hasn’t ducked. If things don’t go as he might wish, he is unlikely to resign, protest, or publicly criticize the president—it is not his way. If Trump tires of listening to him, if he is fired in the usual hail of abuse, regard for him at the Pentagon—the world that for Caine matters most—will not suffer. He has spent most of his military career working in the shadows, with units who brand themselves “quiet professionals.” Unlike many of his predecessors, he hasn’t held a routine press conference and has mostly refused requests for interviews. His inclination is to make himself as invisible as possible. He would like to avoid becoming the story himself, as some of his immediate predecessors have done.
Then Caine was drafted into a June 26 press conference that Trump touted as a “fight for the Dignity of our Great American Pilots.” Caine appeared at the Pentagon with a testy Hegseth, who scolded journalists for covering an initial intelligence assessment of the operation—that the strikes set back Iran’s nuclear program only by a matter of months—and for not being sufficiently grateful to men and women in uniform. Caine followed Hegseth’s rant with a technical review of the bombings, blue marker and laser pointer in hand, and a heartfelt tribute to the “awesome humans” who prepared for 15 years for an operation like Midnight Hammer. At one point, Caine put his listeners in the boots of Patriot missile crews who were charged with neutralizing Iran’s retaliation on U.S. forces in Qatar.
“It’s hot, you’re getting nervous, and you expect an attack,” Caine said, seeming to relish the opportunity to transmit the experiences of soldiers. Then your crew “turns a key and relinquishes control of those missiles to that young lieutenant inside the vehicle. And you wait. You know that you’re going to have approximately two minutes—120 seconds—to either succeed, or fail.”
Especially in contrast with Hegseth, Caine was “almost lyrical,” according to The New York Times. The tone of the press conference was good-cop, bad-cop—so much so that the Reuters journalist Idrees Ali asked Caine if he had been “pressured” by Trump or Hegseth to give “a more rosy intelligence assessment.”
“I’ve never been pressured by the president or the secretary to do anything other than tell them exactly what I’m thinking,” Caine replied, “and that’s exactly what I’ve done.”
Unlike his congressional testimony earlier in June, in which Caine contradicted the president, at the press conference he was on message, taking Hegseth’s cue to focus on the soldiers, not on whether Midnight Hammer had been a true success.
The oath sworn by all U.S. military officers states that “I will well and faithfully discharge the duties of the office on which I am about to enter.” In other words, Caine is obligated to obey lawful orders. He does not make political decisions. He may refuse an unlawful order and argue that point in his defense if he is court-martialed, but he is duty bound to carry out all others, whether he agrees with them or not, even if they directly contradict his advice, even if he believes they are harmful to the country, even if he believes they are immoral. As Joint Chiefs chairman, Caine is required to convey the president’s orders, but there is nothing to stop him from noting his disagreement—in-house, if not publicly. This would be a quick way of provoking Trump’s ire, but Caine told the senators he was prepared to be dismissed from the job if the president didn’t like his advice. He did not seek the position. Trump came looking for him.
Senator Kelly again: “If necessary, will you choose the right thing to do? Even if it is hard over the easier wrong option?”
“Senator, I’ve always strived to do the right thing, and that’s not going to change now.”
Less likely but also possible would be resistance from inside the Pentagon. Caine can relay the orders of the president and the secretary of defense, but there’s no guarantee that the instructions will be instantly obeyed. The service chiefs and combatant commanders who recently outranked him, and who command troops, might not bend. This would not necessarily amount to a public refusal; it could be accomplished by delays or failure to aggressively follow through. For example, the military has obligingly been taking down portraits and scrubbing its websites and curricula of Black and female faces, DEI language, and inclusive initiatives, but decisions about promoting or assigning personnel in the military’s million-plus ranks remain with lower-ranking commanders. While by no means color or gender blind, the military has been and will remain the most integrated institution in America. It is doubtful that orders from Trump’s White House will dramatically alter its culture.
If Trump or Hegseth, through Caine, push policies that top commanders consider unlawful or unwise, they may well be greeted with generous lip service and stubborn inaction. More likely, Caine would convey his objections to the White House himself, ready to be shown the door. For now, though, the president has thanked Caine by name—nickname, too—calling him “spectacular” after the bombing mission against Iran.
There are two schools of thought about how long this will last. Some who know Caine predict that his tenure will be rocky and short. Others believe that his remarkable social skills might see him through to the end of Trump’s presidency. He seems prepared either way. The real test might come if Caine is asked to lie, or to embrace one of Trump’s exaggerations. The president tests his subordinates this way. The supposed “obliteration” of Iran’s nuclear program—an assertion not yet backed by evidence—was one such test, which Hegseth passed but Caine sidestepped during the June 26 press conference. Will the chairman keep evading such a test, and for how long?
Caine exited his first military job—happily—with a swift verbal kick from his commander. No one will be surprised if his last military job ends the same way.
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