Watch Industry SITREP - September 2025

Trump Hangs With The Rolex CEO, A Taliban Casio On Display, Honoring Robert Redford, The Syrian President’s Patek Philippe, & Plenty Of Watch Crime 

By Benjamin Lowry

With September behind us, it is once again time for the W.O.E. SITREP, or Situation Report, our monthly compilation of news and events related to watches, intelligence, national security, and the military, all paired with our (sometimes) informative analysis and discussion. 

The past few weeks have been big for the broader Watches of Espionage community, including President Trump chillin’ with Rolex CEO Jean-Frederic Dufour, a Casio formerly belonging to a Taliban leader on display, Syrian President al-Sharaa visiting the US with a Patek on the wrist, the death of legendary actor Robert Redford, and a whole lot more. 

As always, we also touch on a broad swath of watch-related crime. Many of you expressed disappointment over our alarming lack of Rolex-thieving sex workers in last month’s SITREP, and we are pleased to report that we were able to dig up a sticky-fingered prostitute for this month’s edition. 

That sounded terrible. Let’s just get started. 

President Trump & the Rolex CEO Chillin’ at the US Open 

President Trump and Rolex CEO Dufour at the US Open on 07 September.

It’s not every day the watch industry finds itself at the center of international politics involving the President of the United States, but that’s exactly what happened when Rolex CEO Jean-Frederic Dufour invited President Trump, Pam Bondi, and Steve Witkoff to the brand's private VIP suite at Arthur Ashe Stadium during the US Open men’s singles final on 07 September. Pundits were quick to imply the apparently casual hangout was something more, perhaps serving as a diplomatic effort on behalf of the Crown regarding Switzerland’s crushing 39% export tariff to the US. 

On 24 September, Massachusetts Senator Elizabeth Warren reached out to Dufour, alleging that Rolex was seeking a tariff exemption with its luxurious effort to “curry favor” with the US President. In a typically Swiss, bone-dry response the following day, Dufour noted that while President Trump had indeed joked about whether he had been invited because of the tariff situation, there was no discussion on policy, tariffs, or international relations, and the pair instead focused on the unfolding men’s singles final match. 

Elizabeth Warren’s 24 September letter to the Rolex CEO. (Photo Credit: X/@SenWarren)

In 2024, Rolex managed an estimated CHF 10.58B ($11.23B) in revenue, a number eclipsing the GDP of many nations, meaning the Crown has significant political bargaining power and influence. That said, a 39% export to the US makes a noticeable dent even for a superpower like Rolex, making it hard to believe Dufour’s invite was purely friendly, likely marking a long-game approach to warm and fuzzy relations with the United States. What is true in business is also true in intelligence: nothing is an accident. 

Taliban Founder Mullah Omar’s Casio On Display in Afghanistan

Omar’s Casio W-86 on display in Afghanistan. (Photo Credit: X)

Mullah Omar famously founded the Taliban in 1994, serving as the organization’s Supreme Leader until his death from tuberculosis in 2013. In a recent post on X, Omar’s Casio W-86 (or something similar) is shown in a commemorative shadowbox honoring the Taliban founder in a modern Afghanistan that is, since the US exit in August 2021, once again under Taliban control. The role of inexpensive watches such as the Casio F91W in terror operations is well documented, with the cheap yet reliable digital modules often utilized as timing devices for improvised explosive devices. In addition to Mullah Omar’s Casio, Usama bin Laden also wore a F91W. 

Omar’s Casio appears to be the recently discontinued W-86, a slight upgrade from the more basic F91W that offers 50 meters of water resistance, a larger display, a more comfortable strap, and a better backlight. For the modern Taliban to display Omar’s watch is yet another example of the intriguing dual role played by timepieces, acting as tools and talismans for key figures on both sides of the Global War on Terror. 

Robert Redford, Actor & Wearer of Great Watches, Dies At 89

Redford wore a Doxa Sub 300T in Three Days of the Condor. (Watch Photo Credit: S. Song Watches)

An actor close to our community, having played in several espionage-related roles, Robert Redford died peacefully in his sleep on 16 September, aged 89. Starring in 1975’s Three Days of the Condor and 2001’s Spy Game, both of which are required viewing for the W.O.E. community, Redford’s prolific career also included many notable appearances by important timepieces. Rumored to be his personal timepiece, Redford wore a Doxa Sub 300T on a leather Bund strap in Three Days of the Condor, a masterclass in '70s watch style. In Spy Game, Redford wore a Victorinox Swiss Army Officer’s 1884, the perfect unassuming “grey man” timepiece of the era. 

Redford wearing the watch nerd favorite SKX009 in All is Lost.

Beyond his roles portraying members of the intelligence community, Redford also notably wore his own Rolex Submariner ref. 1680 in 1972’s The Candidate (and several other films) and, one for the nerds, a Seiko SKX009 in 2013’s survival thriller, All is Lost. The depth of Redford’s appreciation for watches is clear, and his extensive filmography presents some of the finest watch spotting for any actor of his generation. 

Adam Boehler Secures Release of Another US Detainee in Afghanistan Wearing a Patek Philippe (Upside-Down?) 

Boehler wearing a GMT-Master II upside down while meeting with the Taliban’s foreign minister back in March.

Adam Boehler is President Trump’s Special Envoy for Hostage Response and at least a little bit of a watch guy with some interesting, upside-down watch-wearing habits. Earlier this year, Boehler arranged the release of George Glezmann, a Delta Airlines employee who made the bright decision to vacation in Afghanistan in 2022 after the US withdrawal. On his wrist during a photo op with Amir Khan Muttaqi, the Taliban’s foreign minister, Boehler wore a Rolex GMT-Master II with an all-black bezel on a nylon pull-through strap. Boehler’s overall look was straight out of central casting, but we were unable to account for why his watch was worn upside down. 

Boehler wearing a Patek Philippe Aquanaut upside-down during a 28 September meeting with Muttaqi.

Well, Boehler is back at it. In a remarkably similar photo from a 28 September meeting with Muttaqi, during which Boehler successfully negotiated the release of Amir Amiri, detained in Afghanistan since December 2024, Boehler wore a Patek Aquanaut, once again on a nylon strap, and once again upside down. Call it a W.O.E. mystery, but unless wearing watches upside down is just Boehler’s thing, it’s hard to guess at why his collection of luxury timepieces is set up this way. As an aside, shoutout to the Taliban’s photographers for their remarkable, wedding photographer-like consistency. 

Syrian President Ahmad al-Sharaa Brought His Patek Philippe to a Sit-Down with General David Petraeus 

On 24 September, Ahmad al-Sharaa (al-Jolani) became the first Syrian President to speak at the United Nations in six decades. On 22 September, al-Sharaa sat down with General David Petraeus in New York with a Patek Philippe World Time Chronograph 5930G, valued at $81,610, on his wrist. This watch was in stark contrast to the black tactical watch he wore as he led his forces’ march on Damascus, and even the Seiko and Omega he switched to shortly after overthrowing the Assad regime. Al-Sharaa’s fatigues have since been replaced with tailored suits and his beard trimmed. 

Al-Sharaa’s watch is a Patek Philippe World Time Chronograph 5930G valued at $81,610.

In intelligence and diplomacy, a watch serves as a tool. In al-Sharaa’s case, the Patek is a tool to telegraph the persona of a diplomat and respectable world leader. And frankly, it’s working. Al-Sharaa is a former member of al-Qaeda in Iraq and the Islamic State of Iraq (ISI). In 2005-2006, he was arrested by coalition forces under Gen. Petraeus’s control. Years later, in New York, Petraeus welcomes the former Jihadist, who until recently had a $10M bounty on his head, with open arms. Maybe Petraeus is a big Patek Philippe fan? 

Perpetrators Smash Windows at Chicago Rolex Boutique, Stealing Five Watches 

(Photo Credit: WGN TV)

It wouldn’t be the SITREP without some felonious watch-related goings on, starting with the smash-and-grab robbery of a Rolex boutique in the 700 block of North Michigan Avenue on Chicago’s Magnificent Mile. According to court documents, six men wielding hammers broke showcases in the boutique before absconding with five watches worth a reported $170,500. 

After a dramatic car chase, the suspects crashed into a parked car and attempted to flee on foot before being swiftly apprehended by law enforcement. Four of the five stolen watches were also quickly recovered. I understand these men were not exactly the stuff of Ocean's Eleven, but how six dudes only managed to steal five watches is beyond me… 

Seven Indicted in the Biggest Jewelry Heist in US History

(Photo Credit: ABC7 News)

In a more organized criminal effort, seven were indicted earlier this month with charges related to the 2022 heist of a Brink’s armored truck at a California gas station during which perpetrators made off with an estimated $100M in jewelry and luxury watches. Setting up the largest jewelry heist in US history, the Brink’s semi truck was laden with gold, diamonds, rubies, emeralds, and luxury watches from fourteen LA area jewelry stores displaying their wares at an international jewelry show in the San Francisco Bay Area. When the truck departed from the show, a team of well-organized thieves followed it for 300 miles before making a move at a gas station in Lebec, north of Los Angeles, eventually escaping with 24 bags of loot. 

It took law enforcement a few years, but it looks like justice will be served for the affected businesses, several of which were forced to close after suffering dramatic financial losses from the heist and extended legal battles over insurance payouts from Brink’s.

“Bad Date Bandit” Arrested & Charged For Rolex Theft In Miami 

Angelina Chenel Esty has been dubbed the “Bad Date Bandit”, which is hilarious.

As promised, this month’s SITREP would be incomplete without a shady lady of the night doing some unauthorized long-term Rolex borrowing. Angelina Chenel Esty was arrested and charged in connection with a robbery in Miami’s Brickell neighborhood. According to Miami Police, Esty and an accomplice met a pair of young gentlemen at a downtown bar who, at some point, suggested the ladies check out their apartment. Once inside, the ladies allegedly drugged the men before stealing a Rolex, about four grand in cash, and another replica Rolex. 

In a shocking turn of events, this wasn’t Esty’s first rodeo, and the young woman had been previously arrested for an eerily similar crime during which she allegedly stole a $20k Rolex Datejust and a diamond bracelet worth around $10k from another man who, with some pharmaceutical help, fell asleep at a bad time. Proof that law enforcement officers do, despite what you may have heard, have a sense of humor, Esty has been dubbed the “Bad Date Bandit”. 

If you like to hang out at the bars in Brickell, we would advise you to leave your Rolex at home. As far as we’re aware, no one has ever been drugged over an Arabic Seiko. Just sayin’. 

Final Thoughts 

From a Jihadist turned head of state flexin’ a Patek to a Casio enshrined by the Taliban, from international business going down at the Rolex box at the US Open to yet another Rolex theft on Miami’s mean streets, September proved that watches are a surprisingly sharp lens for viewing power, culture, and human behavior. The stories range from tragic to absurd, but each underscores one of our core tenets at Watches of Espionage: timepieces are never just about time. Watches are tools, symbols, and sometimes, as the “Bad Date Bandit” proves, bait. 

That’s why we do the SITREP. Because in this world, whether you notice it or not, a watch is always saying something, and it’s our job to figure out what it is. See you next month.

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