Ask Watches Of Espionage Anything, Part III

Ask Watches Of Espionage Anything, Part III

In this edition of the Dispatch, we’ll answer some common questions we get about W.O.E., timepieces and the Intelligence Community at large. Many of these responses can – and probably will at some point–serve as stand alone stories, but for now, here’s some additional insight on Watches of Espionage. If you have any more questions, please ask in the comments section and we’ll address them in a following article.

See past questions “Ask W.O.E. Anything Part I” and “Ask W.O.E. Anything Part II

22 Special Air Service Breitling Avenger Seawolf
22 Special Air Service Breitling Avenger Seawolf with the SAS insignia at 9 o'clock. (Courtesy SAS Melvyn Downes)
  • W.O.E. recently posted a SAS Breitling Avenger with the Special Air Services (SAS) insignia on the dial, do unit watches cause OPSEC issues?

  • We have extensively covered “Unit Watches” from various Intelligence and Special Operations organizations and profiled programs from Tudor, Bremont and Omega.  To summarize, a unit watch is one that is customized by the manufacturer for members of a specific unit or organization inside the military. Civilian organizations inside the NatSec space can also receive these watches, but the term “Unit Watch” almost exclusively applies to military units. Customizations to the watch can include the unit’s insignia on the dial and/or a custom engraving on the caseback.  While more honorific in nature, we have documented many instances of these watches worn operationally overseas.  This has caused many to question if the watch itself is an “Operational Security” (OPSEC) vulnerability.  If an individual is captured, wouldn't the “bad guys” know he was a member of the SAS?

    British SAS G Squadron Richard Williams Breitling Avenger
    British SAS G Squadron Richard Williams wearing a custom 22 Special Air Service Breitling Avenger Seawolf in Iraq.

    The fact of the matter is that most elite units (even Tier One SpecOps) operate overtly most of the time.  While deployed to a War Zone, they’re generally wearing uniforms with their nation’s flags on their plate carriers and are not “under cover.”  While elite units and intelligence organizations certainly have operations where they operate under some form of cover, including posing as businessmen, most of the time this isn’t the case for someone in an “assaulter” role or even CIA Paramilitary Officer.  If an individual is operating under a “Non-Official Cover” (i.e. not a government official) then they certainly would not wear a Unit Watch.  They would pick a watch to match their persona.  Given the rapid proliferation of digital timepieces, many “operators” choose to wear a G-Shock, Suunto or other digital watch while operational, and reserve the unit watch for the garrison.

  • What was the most dangerous thing you did at CIA? 

  • The job of a Case Officer is to collect intelligence– to steal secrets through recruiting and running human assets (“spies”).  It's more dangerous than the average trade, but it's certainly not like it is in the movies. I never got into a fistfight in an elevator, a high-speed chase through a European capital, or performed a risky surreptitious entry into a Russian oligarch's dacha.  Most of my work was discreetly meeting with assets and liaison services in cafes, back alleys, and hotel rooms to collect intelligence.

    Watches of Espionage Afghanistan
    W.O.E. in Afghanistan, early 2000s.  W.O.E. in Sudan, early 2000s, Breitling Aerospace on the wrist.

    The easy answer to this question would be “warzone” assignments, where during the Global War on Terror, IEDs, shootings, and kidnappings were a real and present threat.  That said, in a warzone, Case Officers carry guns, wear body armor and generally operate alongside GRS and/or paramilitary officers.  The most dangerous thing I did was operate alone in Africa, and in one specific capital where crime, terrorism, and counterintelligence risks from the local service were deemed “critical.” 

    African Capital

    During this assignment, I did my cover job during the day and then at night went out on the street alone and without a phone (read CIA Officers and Apple Watches).  After a multi-hour Surveillance Detection Route, I met developmentals and recruited assets in hotels, bars, dark alleys, and cars hunkered down in low-trafficked areas of town.  Most of the time I was unarmed, as being caught with a firearm would have posed significant problems for my cover (see CIA Case Officer’s Everyday Carry - EDC).  The risk from terror groups and the local intelligence service was significant, but the constant exposure to the streets, and everything that comes with that, night after night over a multi-year assignment dramatically increased the probability of carjacking and violent crime, something that can generally be avoided for the average tourist or business traveler.

  • Do you only wear your watches on straps?  How do you feel about bracelets?

  • Watches of EspioangeStrap
    (Photo Credit: James Rupley)

    It is no secret that W.O.E. loves straps. This has led our own line of leather and nylon straps that we designed. I constantly rotate my watches through a plethora of straps and it’s a great way to change up the look and feel of a watch. 

    That said, it is hard to beat a well-designed bracelet and I wear my watches regularly on the original bracelet.  Rolex Oyster and Jubilee bracelets are incredibly comfortable and are probably my favorite.  Most of the watches in my collection, including Tudor, IWC, and Breitling also all come on great bracelets.  The one exception is Seiko and particularly the Arabic Seiko: the bracelet feels cheap and I threw that one in the trash as soon as I got it.  So in short, yes, I am a big fan of bracelets.  After wearing a watch on a nylon or leather strap for a while, it is always refreshing going back to the original bracelet.

    Watches of Espionage Rolex Explorer
    (Photo Credit: James Rupley)
  • How do you store watches and do you use a watch winder?

  • If you have more than two to three watches of value, you need to invest in a safe that is mounted to the wall or floor.  Frankly, no matter what, it is worth acquiring a fireproof safe for valuables, firearms, and important documents.  For years I have kept my watches in affordable (read cheap) plastic cases and put them inside the safe.  Like all of our designs, I have made them for myself and the 6 Watch Storage & Travel Case is exactly the type of case I have used for years (but much better quality than the ones I used to purchase off Amazon).  

    6 Watch Storage & Travel Case

    There are some fantastic high-end watch cases and watch boxes (like Bosphorous Leather) that are true works of art, but it is hard for me to justify spending that type of money on something that will mostly sit in a safe.  There are also some really cool “display cases” on the market, but unless you have a walk-in safe, this is a sign to the goons that reads “take me.”

    Bosphorus Leather “Watch Collector Case” (Photo Credit: Bosphorus Leather)

    I have never used a watch winder.  There is conflicting information on whether a watch winder is good or bad for watches but it generally seems like if you have new watches you should be okay.  That said, many of my watches are vintage and I would not want to keep them winding every day. It’s simply not necessary.  However, the main reason I do not use a watch winder is cost.  A 4 Piece Wolf watch winder starts at over $2,000.  I would much rather use that money to purchase a pre-owned Breitling or Tudor or multiple Seikos. 

    Additionally, I actually enjoy setting the time on my watch each time I pick one up to wear it.  It’s something of a ritual to take a few minutes to wind the watch and set the time.  And yes, I always set the correct time on my watches.

    Watches of Espionage
    (Photo Credit: James Rupley)

    In purchasing a pre-owned Rolex, do "Box and Papers" matter?

    Vintage watch dealer Eric Wind has famously said that, "Saying you only want to buy a vintage watch if it has the original box and papers is the equivalent of walking around a high school with a ‘Kick Me’ sign taped to your back—except it says, ‘Rip Me Off.’ ”  Given his breadth of experience, I will take this at face value.

    Rolex GMT Rootbeer
    (Photo Credit: James Rupley)

    That said, I do enjoy having a “full set” when possible because it’s a neat historical addition to the watch, but I would not necessarily pay the extra premium for a piece of paper that can easily be forged.  A few years ago I purchased an early 1980s “Root Beer” Rolex GMT Master 1675/3 with the original box and papers from the original owner.  The receipt shows the exact day and store where he purchased the watch in the Caribbean.  It’s a piece of living history and part of the story of that watch.  While I rarely look at the paperwork, it is a something I treasure because it’s part of the ephemeral nature of ownership and a sign that the watch has seen plenty before–and hopefully after me. 

    Fake Rolex Box
    One of these boxes is fake, can you tell which? 

    “Box and papers” can add $1,000-2,000+ to the price of a pre-owned watch, and for me, this is simply not worth it.  Of all the things to fake, the papers are the easiest to forge, and boxes are often paired with pre-owned watches and it’s difficult to determine originality.

  • What are some good fiction spy books?
  • There are plenty of great classic espionage fiction authors a la John le Carre and Rudyard Kipling; however, if you are looking for contemporary works, my favorite authors are Jason Matthews (former Case Officer and Breitling owner), David McCloskey (former CIA Analyst), Jack Carr (former Navy SEAL) and David Ignatius (journalist and columnist with Washington Post).  With the exception of Ignatius, all of these authors come from the IC/SpecOps and have real world experience.  

    Watches of Espioange Jack Carr
    (Photo Credit: James Rupley)

    It’s impossible to write about our community with authority if you have not lived it, and each one of these pieces contain little “if you know, you know” nuggets that cannot be faked.  Further, the fiction genre often allows the authors to include details that otherwise would have been removed by the CIA’s publication review. (there have been multiple items in the above books that were removed from my work because they were considered “classified.”)

    Red Sparrow Watches of Espionage
    Movie adaptation of Red Sparrow

    Additionally, it will come as no surprise that watches are mentioned and often play a central role in all/most of these pieces.

    • Red Sparrow trilogy- Former CIA officer Jason Matthews
    • Agents of Innocence - David Ignatious 
    • Damascus Station- Former CIA Analyst David McCloskey
    • Terminal List series- Former Navy SEAL

    For military fiction and the future of warfare, check out 2034 and Ghost Fleet

  • What do you think about the recent Moonswatch/Blancpain releases?

  • I don’t think about them.
  • Why has the W.O.E. platform been so successful?  What advice do you have for growing my Online Journal/Instagram page?

  • W.O.E.’s “quick” growth and high engagement is largely due to the fact that it’s such a niche topic, with broad appeal.  But the real “secret” is authenticity.  This is a passion and a hobby and I never set out for this to be a business.  I genuinely enjoy researching topics and creating products for our community.  In fact, I don’t post on topics that will get high engagement, instead I write about things that I find interesting.  A successful article is one that I enjoyed researching and writing, not one that gets a lot of likes and comments.  The community (you) is not stupid and can see through anything that is artificial, fabricated, or click bait.

    Watches of Espionage

    If you are interested in launching a podcast, newsletter or social media page, my advice is to identify a niche topic that you are passionate about and have a unique perspective on and double down on that. Lastly, this takes time.  While W.O.E. might seem like an overnight success, I have put a lot of effort into cultivating this content to provide this resource to our community. Like with anything, consistency is key.

  • Would you wear a fake watch/Rolex?

  • I can think of very few instances where wearing a fake Rolex is acceptable.

    In response to “Trading A Rolex To Get Out Of A Sticky Situation - Myth Or Reality?” several commenters suggested traveling with a fake Rolex for bartering.  The logic may be sound, but if you are really at the point where you have decided to part with a $5-10k watch, your life is likely on the line and the cost is trivial.  Further, whoever you are giving the watch to is presumably in a position of power and likely someone you do not want to piss off should they determine the watch is fake.

    Fake Rolex
    Seized fake Rolex by US Customs and Border Protection

    I have heard of some people with expensive watch collections that have “dummy” displays in their house, the idea being that if someone breaks in to steal their collection, they would take the fake watches without realizing the real collection is hidden in a safe.  This is something that could potentially make sense, but is not necessarily something I would advise.  If someone goes the distance to specifically target you for your watch collection, they are likely going to be pissed to find out they stole fake watches, and may come back for retribution.  No watch is worth your life.

    Fake Rolex Dubai

    All that said, I do have a fake Rolex Submariner that I received as a gag gift from a wealthy friend in Dubai.  I have never worn it or even taken out the links to fit it to my wrist.  Who knows, maybe it will come in handy one day.

  • How accurate is your portrayal of your life and W.O.E.?

  • When it comes to long-form writing, all of my stories and personal anecdotes are 100% accurate.  I have several friends from the community that read the Dispatch regularly and my Signal messages would immediately light up if I started making up there I was stories for clout.  Of course, I do change times/dates/locations and minor details for the sake of anonymity (or if the CIA’s Prepublication Review Board advises I do so).
    Watches of Espionage Sudan

    In many ways, being anonymous allows me to be more honest in my writing.  I recently posted a picture of my entire watch collection.  This could easily be construed as bragging about material possessions and is something I would never do on a personal social media account.  In fact, most of my close friends don’t even know about the number of watches I own or the value of my watch collection.  Anonymity permits me to engage in a form of honesty that would otherwise be self-corrected. 

    Watches of Espionage Jedburgh Strap

    While my portrayal of my life and thoughts are genuine, I do think a lot of people interpret this as a persona of something I am not.  I am not a commando or Jason Bourne.  I am a (relatively) normal guy who is fortunate enough to do some abnormal things with extraordinary people.  For that I am very grateful.

  • What is the future of Watches of Espionage?
  • Our goal for Watches of Espionage is to become the number one resource for military, intelligence, and NatSec content and products as it relates to timepieces. Long-form written articles are our main product, and we intend to keep this free and open for everyone to learn from.

    Watches of Espionage GBRS Group

    In 2023, we set the foundation for this expansion with the establishment of the website, development of some incredible products, and expansion of written form content. We raised $24,800 for Third Option Foundation and we have more fundraisers scheduled for this year that will be both meaningful and interesting.

    We have resisted offers from advertisers so that we can maintain complete editorial control of our content.  Remaining authentic and representing our community respectfully is key to our past and future success and we will not sell out for a quick buck.  W.O.E is and always will be an enthusiast platform solely for our community, and it's not for everyone.

    Watches of Espionage EDC Valet

    Over the coming year, we hope to expand the number of articles per week and potentially move into other mediums.  Regarding products, we are happy to now have W.O.E. products in stock and we are working on some new and exciting projects for 2024, including some EDC items.  We are also still in the initial stages of producing W.O.E. content in a print medium, something that we are being methodical about to make sure we get it right.

    We appreciate those who have supported W.O.E., as this support will give us the opportunity for increased quality content and products.

    As always, thank you for the support.  This would not be possible without you.

    Stay tuned,


    If you enjoyed this article, please consider signing up for our weekly free newsletter for further updates HERE.  


    This Dispatch has been reviewed by the CIA’s Prepublication Classification Review Board to prevent the disclosure of classified information.

    READ NEXT: Best Watches Under $1,000 - Ask the Experts

    Watches of espionage


    Is the recruiting process for the Agency stringent on dual citizens? Do you know what’s life like for a case officer on the Far East stations like say, Manila? In general, is the life of a spook in the far east much easier or difficult compared to other stations globally?


    For your book recs is it 2034 by Elliot Ackerman and Ghost Fleet by PW Singer?


    I’ve been reading you for a long time, it’s interesting!
    Tell us something about Russia, is it difficult to work here, is the level of our intelligence services high? I want to know exactly your opinion.


    You’ve mentioned Seiko is the Toyota of watches. Do you have any thoughts on Citizen?


    “I am a (relatively) normal guy who is fortunate enough to do some abnormal things with extraordinary people.”

    Fantastic line. I enjoy the work you put out and your humble approach to storytelling.


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