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 be 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 briefing today, 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!
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 Rolex Submariner. 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.
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.
