We are living through some surrealistic days, and as you are probably aware the United States and Israel recently attacked and declared war on Iran, which may very well represent the beginning of World War 3.
War is a terrible, and my goal with this article is not in any way to glorify or justify it, but to share the fact I noticed in a Pentagon briefing today in Washington D.C., Chairman of the Joint Chiefs of Staff, General Dan Caine was rocking a Rolex SKY-DWELLER as pictured below as he discussed "Operation Epic Fury":
In the high resolution image below we can made a 100% positive ID that confirms General Caine is wearing a Rolex SKY-DWELLER, and my best guess is that he is wearing a Rolex 42MM Rolesor Oystersteel and white gold model Reference 336936 with an intense white dial, which typically comes on a Jubilee or Oyster bracelet, but as we see, the General put in on a black aftermarket rubber strap.
One of the most interesting details about General Caine's Oystersteel and white gold SKY-DWELLER is it looks remarkably similar to Rolex's White Gold SKY-DWELLER which is pictured below.
The Oystersteel Rolex Rolesor model (pictured below) only comes standard with either an Oyster Bracelet, or a Jubilee bracelet, but General Caine put his on an black aftermarket rubber strap, which makes it look very similar to the White gold model pictured above, which has a current retail price of $50,850.
Pictured below we see the Oystersteel version which retails for $17,750, and they pretty much look identical. The ONLY visible difference I notice is the white gold variant (pictured above) comes on a Rolex OysterFlex bracelet/rubber strap, and it includes white gold solid end links, which give it a more polished look.
If you look closely at General Caine's SKY-DWELLER you will notice his rubber strap lacks the solid end links (SOL). So basically, he took the Oystersteel model (pictured below), and by putting a black rubber strap on it, made it look like the almost three times more expensive all white gold model pictured above. I doubt he did this try and make it look like the more expensive model, but likely just prefers the beautiful looking high contrast look and simplicity of the black strap with the bright white dial, which is brilliant!
Below we see General Caine's Rolex SKY-DWELLER from a better angle where you can really make out the details in a photo that appears courtesy of the United State Department of War and was taken by PO1 Alexander Kubitza.
Below is an image that appears courtesy of the Department of War that shows the Operation EPIC FURY Timeline for the first 100 hours, which is fascinating on many levels.
Below is another image of General Caine rocking his Rolex SKY-DWELLER. Chairman of the Joint Chiefs of Staff Gen. Dan Caine met with Airmen from the 162nd Wing at Morris Air National Guard Base, Ariz. Dec. 5, 2025. (DOW photo by Chief Mass Communication Specialist James Mullen).
I remember when Rolex first introduced the Rolex SKY-DWELLER, back at BaselWorld in 2012, thinking to myself, "I wonder what SKY-DWELLER means as a name, or what it stands for?" Now that I think about it, I can't think of a more fitting or appropriate name for a Rolex model that a 4-star Air Force General, who is also the Chairman of the Joint Chiefs of Staff would wear!
If you want to watch the entire press conference briefing on the U.S.-Iran war, you can check it out below. It's difficult to put into words, how over-the-top crazy-insane this situation is!?!!:
If you just want to watch General Dan Caine's comments while rocking his Rolex SKY-DWELLER you can watch it below:
When I was doing research for this story on General Dan Caine, I came across this image that shows him recently with United State Marine Corps Lieutenant General, Michael J. Borgschulte, rocking his Black Bezel Rolex GMT-Master. This photo was taken on August 30, 2025, at the United States Naval Academy versus the Virginia Military Institute Football game in Annapolis, Maryland.
I originally published the story seen below back on June 25, 2025:
Several readers wrote in to share images of The Chairman of the Joint Chiefs of Staff, U.S. Air Force, General, Dan Caine rocking his Rolex GMT-Master as pictured below.
Special thanks to Nick Gould (Eagle Eyes) discovered and shared the images above and below with me.
Rich wrote in and provided the image seen below and said:
Jake,
Saw this on Fox News. White House Chief of Staff Susie Wiles likely wearing a Datejust.
Not sure what Gen. Caine is wearing or even doing in this photos! As a Tudor owner I very much enjoy your site. It’s both informative and entertaining, something which isn’t easy to accomplish. I’ve shared it with numerous “watch buddies.”
Please keep up the great work.
Rich
The video below features Joint Chiefs of Staff Chairman, Air Force, 4-Star General, Dan Caine briefed the American people on June 22, 2025, as part of Operation "MIDNIGHT HAMMER", which he goes into detail on in the video below.
There have been many 4 star General's, and top Rolex Military Leaders who have worn Rolex watches, and I am including a few images below for frame of reference. First we see, U.S. General, Gruenther, who was the recipient of Rolex's 200,000th Officially Certified Swiss Chronometer.
Next we see General David Howell Petraeus, when he was the 10th Commander of U.S. Central Command.
Sometimes when I am researching a story, I come across one of my old stories that is so cool and timeless I feel like I have to bring it up to the top of Jake's Rolex World, which is the case with this cool post I originally published a dozen years ago in 2012:
Denzel Washington is one of the greatest actors of our time having been nominated for 9 Academy Awards, and and having won the coveted Best Actor Oscar for Training Day in 2002. Denzel and Rolex have a great deal in common as they are both timeless, instantly recognizable and highly iconic.
My pal James from WatchesInMovies.info sent me a message to let me know he just put up a post with images of Denzel Washington sporting a stainless steel Rolex Submariner from the 1996 movie "Courage Under Fire."
David Petraeus is the current Director of the United States Central Intelligence Agency. He was appointed CIA director on September 7, 2011, and he has been wearing his trademark Rolex Submariner for many years.
Prior to becoming the Director of the CIA, David Howell Petraeus was a U.S. Army 4-star General and the Commander of the United States Central Command. General Petraeus has an extremely distinguished career and he was one of many Top Military Leaders to wear a Rolex.
This first photo appeared in Vanity Fair magazine and shows General Petraeus' Rolex Submariner with Oyster Bracelet. You can learn more and see more photos of General Petraeus in an article I wrote about Rolex On Top Military Leaders.
U.S. Central Command
Geographic Scope
The United States Central Command (USCENTCOM) is a theater-level Unified Combatant Command unit of the U.S. armed forces and its area of responsibility is in the Middle East, including Egypt and Central Asia as we see in the map below:
Wristwatches in general owe their genesis to the military. Before World War I, only women wore wristwatches. Men wore pocketwatches, but in warfare timing is everything, so if a soldier had to unbutton his overcoat, then unbutton his jacket to get to his pocket watch to see what time it was, he could get in a lot of trouble–especially if he was freezing in a muddy trench and had to hold his gun with one hand.
That's why soldiers during World War I started wearing wrist watches. Wristwatches allowed a soldier to simply glance at his wrist to see what time it was.
Military leaders have relied on Rolex since before Swiss Army General Henry Guisan put on the 50,000th Officially Certified Swiss Chronometer that Rolex made in 1946.
Let's begin by looking at U.S. Army 4-Star General David Howell Petraeus. General Petraeus is the 10th and current Commander of U.S. Central Command.
General Petraeus has an extremely distinguished military career and it comes as no surprise that he depends on his Rolex Submariner to keep time.
General Petreaus was recently selected as one of the world's top 100 public intellectuals in a poll conducted by Foreign Policy and Prospect Magazines. Time Magazine named General Petreaus in 2007 as one of the 100 most influential leaders and revolutionaries of the year.
General Petreaus previously served as Commanding General for the Multi-National Force in Iraq.
As Commander, General Petraeus oversaw all coalition forces in Iraq.
General Petreaus has an amazing military career, but let's go back to beginning and take a look at military leaders who wore Rolex.
Swiss Army General Henri Guisan is Switzerland's most beloved protector in history. Guisan protected the Swiss from the Nazi's during World War II. Gusan not only wore a Rolex, but was given the 50,000th Officially Certified Swiss Chronometer that Rolex ever made.
Rolex gave Sir Winston Churchill with their 100,000th Officially Certified Swiss Chronometer which was a Rolex Datejust in Pink Gold.
Rolex chose U.S. General, Dwight D. Eisenhower as the recipient for their 150,000th Officially Certified Swiss Chronometer. Eisenhower is pictured below, briefing U.S. Army Airborne Paratroopers on the morning of the D-Day invasion he architected to save Europe and the rest of the world from Nazi aggression.
U.S. General Gruenther was the recipient of Rolex' 200,000th Officially Certified Swiss Chronometer which you can see in the photograph below.
Lord Mountbatten of the British Admiralty was also a big fan of Rolex watches. Mountbatten was so proud of his Rolex watches he gave Rolex permission to publish the fact that he wore them, but Rolex of Geneva decided no to exploit this fact for commercial gain.
Rolex & The Right Stuff
In 1947, when Chuck Yeager broke the speed of sound barrier for the first time in history he was wearing his Rolex Oyster as seen in the photo below.
Many years later, we see General Yeager wearing his "James Bond Submariner" in the photo below. To this day, General Yeager still wears a Rolex. This means he has been wearing Rolex watches continually for 7 decades straight–pretty amazing if you think about it.
Chuck Yeager and Scott Carpenter were both part of "The Right Stuff" and Scott Carpenter (pictured below) went on to the U.S. Navy SEA-LAB program that helped Rolex develop the Rolex SEA-DWELLER.
It should come as no surprise that military leaders throughout modern history have depended on their trusted Rolex watches.
Since we were on the subject of Captian Chesley Sullenberger who began his career in the Air Force flying F-4 Phantom II fighter planes, I thought I would share this photo of Chuck Yeager that was taken at Edwards Air Force Base Test Flight Center in 1953–and of course Chuck is wearing his trusted Rolex.
This photo was taken 56 years ago and Chuck Yeager still wears a Rolex to this day. When he broke the sound barrier in 1947 he was also wearing his Rolex Oyster which was 62 years ago. Click the image below for better detail:
Alert: It has come to our attention after publishing this story that the authenticity of the enameled dial on this watch is questionable. This information comes from one of our resident experts, and author of 100 Superlative Rolex Watches, John Goldberger who said:
"This dial was manufactured in the 1990's in Switzerland and the original cloisonné dial was supplied in the 1950's from Cadran Stern Frerés company and they never manufactured a dial with the American Eagle. I think also there is a mistake in the Latin "motto" on the dial! A few of these watches appared in some European Auctions, one of these had a letter from Rolex , but the truth is Rolex doesn't know anything about the provenance of the dial. The quality of the dial is very good but it's 100% fake."
John Goldberger is one of the foremost experts on vintage Rolex watches on planet earth and I trust his evaluation. I did notice the misspelling of "E Pluribus Unum" with the second "U" in "Unum" being an "I" but I assumed it was because the enamel had fallen off.
American Eagle Rolex
I have never been a big fan of watches with hand enameled dials, but I must say this Rolex completely blew me away when I first saw it. According to the owner "It is a super rare Eagle Logo made for a U.S. General and it has all the paperwork and provenance from Rolex."
Many years ago Rolex used to do custom work, but I don't think they offer custom services anymore. The watch was probably made before 1956 because the watch has the Seal of the United States that says, "E Pluribus Unum" which means "Out of Many, One." The reason it must be pre-1956 is because the U.S. changed the seal in 1956 to say "In God We Trust."
The design of this Rolex is very interesting because it has a definite 1950s Populux vibe, with the unusually interesting dauphin hands with the missing lume. I assume the lume disintegrated over the years, but it makes the hands look even cooler.
Also, the juxtaposition between the eagle and the Rolex crown is fascinating because they are both internationally renowned symbols of distinction.
Historically Rolex has always been extremely secretive and discreet, and no journalists in the past have ever been invited "INSIDE ROLEX" to explore and report on all four Rolex Manufacturing faclities in Switzerland.
In November 2013, this changed when Rolex invited Jake to take an unprecdented journey into the heart of Rolex to learn and report on everything he witnessed and learned.
This Super-Detailed 3 Part Story is a "MUST READ" story for anybody who wants to understand what really makes Rolex tick.
