The Watches of General Dan “Razin” Caine

The Chairman of the Joint Chiefs is one of us, with notable timepieces from Rolex, Breitling, and Tudor 

Regardless of where you lie politically and whether you think recent events are justified or wise, the United States military has displayed extreme proficiency over the past year. As always, we remain apolitical as a platform and use watches as a medium to view current events and national security. At the center of this military activity is Chairman of the Joint Chiefs of Staff General Dan "Razin" Caine.

From the precision airstrikes targeting Iranian nuclear facilities in June to the surprise capture of Venezuelan President Nicolás Maduro in January, to the ongoing conflict in Iran, General Dan Caine has been a constant at the pointy end of military affairs. As these historic events unfolded one by one, Caine displayed an impressive collection of watches from Rolex, Breitling, and Jaeger-LeCoultre. He is, without a doubt, one of us. 

Caine wearing his Rolex GMT-Master II shortly after a flight. (Photo Credit: US Air Force)

As we like to say, members of the W.O.E. community are everywhere, including the senior leadership of the military and government. In the United States, the highest-ranking military officer at any given time serves as the Chairman of the Joint Chiefs of Staff (CJCS), the principal military advisor to the President, the Secretary of Defense, and the National Security Council. This is an apolitical position.

Since taking office in April 2025, CJCS General John Dan “Razin” Caine has been as active in overseeing complex military operations as he has been with his watch game, which includes notable tool watches from some of the biggest names in Swiss luxury. In this Dispatch, we’ll discuss General Caine’s collection, how his background influences those watches, and the role timepieces play for the White House’s senior military advisor. 

US Air Force General John Daniel "Razin" Caine

Caine’s GMT-Master II reference 116710LN, captured up close by a White House insider.

Dan Caine joined the US Air Force after graduating from Virginia Military Institute’s (VMI) Reserve Officer Training Corps in 1990, serving largely as an F-16 pilot before rising to the upper echelons of military and government service. Twice deployed to Iraq in support of Operation Iraqi Freedom, Caine has accumulated 2,500 flight hours and earned the Distinguished Flying Cross as well as two Bronze Star Medals. Before taking over as CJCS, Caine also served in key special operations leadership roles, including as the deputy commanding general of Special Operations Command Central from 2018 to 2019. 

Closely tied to the intelligence community, Caine also acted as CIA's Associate Director for Military Affairs (ADMA) from November 2021 until December 2024, and this dual background in aviation and special operations comes through in the watches Caine wears as the Chairman of the Joint Chiefs. 

A Rolex GMT 

Caine’s go-to appears to be his Rolex GMT-Master II reference 116710LN.

We were aware of Caine’s Rolex GMT-Master II reference 116710LN since shortly after he came into office, but the watch’s rise to prominence began after he wore his GMT in the White House situation room during the June 2025 B-2 Stealth Bomber strikes on Iranian nuclear facilities. With close ties to both the aviation and intelligence communities, a Rolex GMT is an appropriate choice, no doubt informed by Caine’s professional background. 

We are also pleased to report that Caine’s GMT is well-worn, demonstrating the type of strict adherence to the Use Your Tools ethos that will earn you big points around here. As often as he wore it, we would have been forgiven for thinking the GMT was Caine’s go-to timepiece, but like an onion, the Chairman has layers. 

Breitling B-1 US Air Force Weapons School Unit Watch

CJCS Dan Caine wearing a Breitling B-1 unit watch. (Photo Credit: DVIDS)

In a photo dated 01 April, Caine wore a Breitling B-1 unit watch with the US Air Force Weapon School crest at nine o’clock while speaking to reporters about the ongoing Iran War. Interestingly, this press conference occurred in the lead-up to the rescue operation for the two F-15E airmen in Iran, which may have been a subtle message that he also comes from the ranks of pilots. 

The B-1 is, along with the Aerospace, one of the most common modern platforms for Breitling’s once-proud unit watch program. Graduates of the US Air Force Weapons School (USAFWS) are known as “Patch Wearers” and considered among the USAF elite. Caine graduated from the US Air Force Weapons School Instructor Course in 1999, making the watch an intriguing memento of his service at the apex of military aviation. 

Caine’s USAFWS Breitling B-1 alongside his VMI class ring.

Where the plot thickens is that shortly after downloading said image showing said Breitling, the photo was removed from public government databases and the internet at large. While we can’t be sure why the image was scrubbed, it’s still sketchy, and we’re always happy to see a Breiting in active service. In addition to his Breitling and his Rolex GMT, Caine has also reached for another, largely overshadowed watch from the Crown as the early stages of the Iran War unfolded. 

A Seldom-Seen Sky-Dweller 

In recent months, Caine has favored a Rolex Sky-Dweller, possibly reference 336936, on an aftermarket rubber strap.

Shortly after Operation Epic Fury kicked off on 28 February, the White House released photos from the makeshift situation room at Mar-a-Lago. We were quick to notice something new on Caine’s wrist, a Rolex Sky-Dweller, likely reference 336936. While its name and dual-time functionality make sense for the Chairman, the Sky-Dweller is a decidedly deeper cut than other Rolex models, and the fact that he has equipped the watch with an aftermarket rubber strap is further evidence that he’s as much of a watch nerd as anyone. 

Caine’s Sky-Dweller is evidence of the senior military leader’s deep appreciation for watches.

If there is one theme in General Caine’s collection, it is the sky and aviation, which makes a lot of sense if you think about it.

Jaeger-Lecoultre Polaris Geographic

General Caine has made several appearances wearing a rare JLC Polaris Geographic.

Arguably, the one outlier in Caine’s collection is his Jaeger-Lecoultre Polaris Geographic, a dual time watch providing a measure of world-time functionality by way of an internal cities disc located at six o’clock, rotated with an additional crown at ten o’clock. It doesn’t seem to be a watch he wears a lot, but Caine wore the obscure JLC during a July 2025 meeting with his South Korean counterpart in Washington, DC. 

Jaeger-Lecoultre is a storied Swiss watchmaker that, despite having at least some caché in the tool watch arena, is seldom encountered on W.O.E. Still, the Polaris Geographic provides genuine utility for a traveling Joint Chiefs Chairman while acting as a more obscure choice compared to his more mainstream Rolex models. 

But how does he afford them?

Caine’s four-watch collection is worth at least $47,700.

Whether we like it or not, a collection of luxury watches like Caine’s comes with a significant price tag. Without taking into account his Basic Allowance for Housing (BAH) or other stipends, which are likely significant, a four-star general (Caine was promoted to four-star shortly before being confirmed as the CJCS) with 36 years of service earns the statute maximum military base pay, $18,999.90 per month, for an annual total of $227,998.80. 

That is a nice chunk of change, but is it enough for Caine to reasonably afford a Rolex GMT-Master II that was around $8,450 (upon its discontinuation in 2019), a Sky-Dweller at $17,750, a JLC currently priced at $18,000, or a Breitling B-1 that could have set the general back as much as $3,500 (the B-1 was discontinued in 2006). 

Whether he’s the CJCS or not, we love to see a military aviator with a Rolex GMT. (Photo Credit: DVIDS)

As it turns out, resting atop the US Military hierarchy is not Caine’s only business venture; the general founded The Caine Group, a homeland security and defense-focused investment and consulting firm, in 2010. Since then, Caine has also joined several venture capital firms as a partner and consulted with various space and air-related companies. The CJCS’s Air Force service biography describes him as a "serial entrepreneur and investor", which makes his expensive watch collection easier to understand. 

Final Thoughts 

Viewed holistically, General Dan “Razin” Caine’s watch collection tells a story far richer than its estimated $50k value. A well-worn Rolex GMT-Master II in the White House Situation Room, a Sky-Dweller at Mar-a-Lago, an obscure JLC Polaris Geographic in a diplomatic meeting, and a Breitling B-1 bearing the coveted insignia of the United States Air Force Weapons School, each timepiece in Caine’s arsenal reflects a different chapter of a career spent at the leading edge of American power and influence. 

Caine presiding over the Change of Command for the legendary USS Nimitz in 2025 while wearing his Rolex GMT. (Photo Credit: US Navy) 

For a senior military leader like Caine, these watches aren’t trophies accumulating secondary market value in a safety deposit box; they’re tools chosen by a fighter pilot, a special operations leader, an intelligence liaison, and now the nation’s senior military advisor. 

Regardless of politics, Caine understands something that is at the core of Watches of Espionage: at the highest levels of war and statecraft, details matter, and you can learn a lot from the watch on someone’s wrist. 

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