What’s Your Grail Watch? W.O.E. Asks the Experts

If cost and scarcity didn’t matter, which watches would former intelligence officers, watch industry pros, firefighters, and Navy SEALs want for their personal collection? 

Though I am technically a “watch collector” because I own quite a few watches, to me, the real value is not in how many watches I can buy but rather in the relationships I have developed with certain timepieces through shared experience. A key aspect of the Use Your Tools ethos is understanding that, while we appreciate watches for their mechanical or aesthetic properties, the real value is derived from the moments in our lives we share with these useful objects. A Seiko or a G-Shock can be as meaningful as a Rolex GMT, and it’s not all about the benjamins. 

With that being said, certain watches out there are more, and sometimes a lot more, than the sum of their parts, and I admit there are watches I have no personal relationship with that I can’t help but covet. Watch nerds on Reddit throw the term around loosely, but for us, a “grail watch” is a meaningful, deeply desired timepiece that you will likely never obtain due to scarcity, cost, or some combination of the two. 

If nothing else, the grail watch conversation is an intriguing thought experiment, so for this Dispatch, we asked prominent members of the W.O.E. community which watches they would have if they could have anything. Their answers didn’t disappoint. 

W.O.E. 

The Complete Set of Military-Issued Tudor Submariners

Price: Lots. 

This Rolex MilSub ref. 5513 hammered for $270,273 last year. Insane. (Photo Credit: Christie’s)

The easy answer for me would be a full spec Rolex “MilSub,” either reference 5513 or 5517, complete with fixed spring bars, a fully demarcated 60-minute bezel, sword hands, and preferably issued to the Special Boat Service. But these watches have become so mainstream that they fetch prices well over $200k, and the whole idea makes it unpalatable, at least for me. 

My real grail isn’t a single watch, but a series of watches. This breaks the rules of the exercise, but this is my platform, and I do what I want. My grail is to own a Tudor Submariner from every country that issued one, specifically Argentina, the United States, Israel, France, Canada, South Africa, and Jamaica. I currently have a South African black “Snowflake” 7016 from approximately 1974, a US Navy-issued 7928 from the early 1960s, and an Israeli-issued 7928 used by Shayetet 13 (S-13) frogmen.

W.O.E.’s South African Navy-issued Tudor Submariner 7016. (Photo Credit: James Rupley/W.O.E.)

Compared to a British Rolex MilSub, these watches are actually somewhat attainable, but securing a complete set of genuine issued pieces is a challenge. I am convinced that the majority of known French Marine Nationale (“MN”) Tudors in circulation are fake. To complete the set, I would like the watches to have a clear lineage and concrete provenance linking them to known practitioners, not having been passed around by various dealers for decades. Will I ever actually make it happen? We’ll see… 

Benjamin Lowry - W.O.E. Team Member, USCG Veteran, Commercial Diver, & Curator of @SubmersibleWrist 

US Navy-Issued Doxa 300T Conquistador 

Price: I don’t think anyone has a clue, but a lot.

One of the few surviving examples of a 300T Conquistador with its helium escape valve at nine o’clock. (Photo Credit: Dr. Peter Millar)

In the arena of military dive watches, there is one story and one watch that lives so deeply within the cracks that it has become the stuff of legend, hearsay, and conjecture, and that watch is the Doxa 300T Conquistador. Unveiled in 1968 or ‘69, the Conquistador was, along with the Rolex Sea-Dweller, one of the first commercially available watches equipped with a helium escape valve for use in saturation diving environments such as the US Navy’s SEALAB or Cousteau’s CONSHELF experiments. 

A vintage Doxa advertisement mentioning the Conquistador. (Photo Credit: Dr. Peter Millar)

The Sea-Dweller went on to become an icon, but the Conquistador, produced in extremely small numbers, faded into obscurity. The Navy’s use of the standard Doxa Sub is well established, but a select number of Conquistadors are also believed to have been ordered and used by the US Navy and specifically the Navy Experimental Diving Unit (NEDU), which was responsible for saturation diving research. If one of these ever came up for auction, I’m not sure anyone would even know how to price it, but I can confidently say it’s out of my price range. 

Jason Heaton - Freelance Writer, Author, & Co-Host of The Grey NATO podcast. Jason’s Substack

1980 CWC Royal Navy Diver (Automatic) 

Price: These don’t trade often, so I don’t have a good sense of what one would cost. If I had to guess, I’d think between $10k and $15k. 

(Photo Credit: CWC)

This is the watch that was chosen by the UK’s Royal Navy to replace the Rolex military Submariner. Enough said! As I wrote in my story for Hodinkee in 2017, “the rare 1980/81 automatic CWC divers are truly special, representing a transitional period in military dive watches, a 'changing of the guard,' so to speak, from Rolex to CWC, and a bridge from mechanical to quartz. The appeal of a Rolex MilSub is that it is essentially a watch from a large luxury brand customized to the specifications of a military unit for a unique purpose. 

But the appeal of CWC watches is that they were created from the get-go to be nothing more than military instruments, with no pretense or evocative name—Submariner or Seamaster—just a caseback stamped with codes and stock numbers. To those who appreciate the stripped-down utility of dive watches, or military watches in general, the CWC diver might just be the best example.

(Photo Credit: CWC)

These are tough, functional, yet visually pleasing watches, representing the end of an era of mechanical timepieces used by an active military diving unit. The quartz versions are still being issued in smaller numbers today, to certain specialist units. While for many, a “grail” is something exotic from a luxury brand, I love an underdog, and CWC is definitely an underdog, but one with bite. 

Derek Haager - Diver, Writer at Monochrome Watches. @derekhaager 

Tornek-Rayville TR-900 

Price: A recent example sold at auction for $114k. 

(Photo Credit: Menta Watches)

This watch has been my personal grail since the moment I learned of its existence. Basically a Blancpain Fifty Fathoms in disguise, it embodies everything I love in a “purpose-built” tool watch. These are anti-reflective, anti-magnetic, fixed-barred, waterproof tanks that were produced for and issued to special forces and never publicly available. They’re extremely rare, as most were destroyed or buried as low-level radioactive waste. Oh yeah, did I mention they are radioactive? That and the fact that the brand name was invented to circumvent the rules of the establishment give them that little bit of punk rock subterfuge that really seals the deal for me.

James Stacey - Editor-In-Chief of Hodinkee & Co-Host of The Grey NATO Podcast @jestacey

Breitling Aerospace (K-Series, 40mm, in solid gold). 

Price: $15,000 or more. 

(Photo Credit: Wright Auctions)

I know the W.O.E. audience has a soft spot for Breitling, and I have a soft spot for the 40mm Aerospace models. Among the fray, alongside more field-ready options like the E56062 (which I wish I had never sold), the grail has to be a K-series "Repetition Minutes" in solid yellow gold. Only available second hand and with pricing hovering in the $15,000+ area, while perhaps not the best option for toolish intent, it is a sort of pinnacle for the Aerospace. And while I'd want to have the bracelet, I think it would sing on a NATO. A quartz, rider tabbed, ana-digi pilot's watch in solid gold. I mean, c'mon.  

Dave Hall - Retired Navy SEAL, Strategic Advisor, & President of The Silent Warrior Foundation. @davehall1911

Breitling Compass Explorateur, Ref. 80940 

Price: $800 to $2500 on the secondary market but very rare. 

(Photo Credit: Grailium)

In early 1986, as I graduated high school and joined the Navy, I was faced with a daunting decision: purchase the Citizen Aqualand or the Breitling "Compass watch". I chose the Aqualand back then. Knowing what I know now, I would have purchased TWO Bretling Explorateurs instead. The black hinged case hid a removable and very functional compass. The black rubber strap also had International Morse Code molded into it. The whole package screamed commando tool. The advertising art for this watch was also provocative for someone pursuing a clandestine career. It's the one that got away that I still keep my eyes out for to round out my collection. 

The Pilot's Watch - @thepilotswatch 

Omega Speedmaster 105.003 Blue ‘Soleil’ 

Price: $40,000, at least. 

(Photo Credit: Hairspring)

I don't normally think in terms of grails that aren't achievable because I don't think that's particularly productive. There are incredible watches that are far out of my budget, and unless I win the lottery or have a second career that makes a stupid amount of money, I know they aren't for me. Based on the definition of a grail, that is something I will likely never acquire, I could go with anything, and there are plenty of watches I could never afford that I would love. That being said, deciding on an unattainable grail was actually fairly easy. I'm picking the inspiration for my current obtainable grail or milestone watch, which is the 2024 Omega Speedmaster First Omega in Space. 

(Photo Credit: Hairspring)

One of the coolest things about that watch is the inspiration for the dial, which is based on a very limited run of dials that were featured primarily on the Speedmaster Ed White 105.003. These dials are so rare that for decades they were thought to be fake, and their origin is still not entirely known. So for me, my unobtainable grail is the Speedmaster 105.003 featuring the blue sunburst Soleil dial, of which there are likely fewer than 20 examples in the world. The history of the Speedmaster and aviation is legendary and something I need not re-examine. These are absolutely tools meant for use. This specific pre-moonwatch reference has the legendary Caliber 321, a flat link bracelet, and one of the best dials I've ever seen. It's a watch that, at 60 years old, still has some G's left to pull. 

Joe Dawson - Former Navy SEAL, Founder & Lead Instructor at Bruiser Industries, & Watch Enthusiast @bruiser_joe

Blancpain Tribute To Fifty Fathoms No Rad Limited Edition

Price: $25-30k. 

(Photo Credit: Bucherer)

There is just something about one of the original divers that is one of the nicest tool watches made, but nobody would notice or appreciate it other than a watch guy. The history of Blancpain and the Fifty Fathoms is undeniable, and I’m an enormous fan of black dial divers with history. The Fifty Fathoms has such an incredible military and diving pedigree, yet it isn’t as highly marketed as the Rolex Submariner and doesn’t carry the same “flex” mentality. The limited edition “no-rad” just has that throwback serious vibe, but paired with modern moment and materials, and in the larger size range I prefer. It has been and will continue to be my grail until I can land one. 

James Rupley - Co-founder of Vickers Guide & Headstamp Publishing. Photographic Contributor to W.O.E. @jamesrupleyphoto 

Rolex GMT Master II, Reference 16710BLRO “Pepsi” 

Price: Tough to say, but a lot, assuming I could actually find one... 

Rolex 16710 belonging to a friend. The watch was purchased from the original owner and included a hang tag with the “BLRO” suffix on the reference number, indicating it was “born as” a Pepsi. (Photo Credit: James Rupley)

My grail watch is a Rolex GMT Master II, reference 16710BLRO, which was certifiably “born” as a “Pepsi”. The GMT Master II reference 16710 hit the market in 1989 with one bezel color option only – red/black (or “Coke”). This red/black bezel continued to be the only color option for approximately 11 years (out of a roughly 18-year 16710 production run), when at some point between 2000 and 2001, two new bezel color options were added: blue/red (“Pepsi”) and all black.

If one considers the fact that a “true” Pepsi 16710BLRO was only produced for approximately 7 years of the 18-year 16710 production run, and that during those 7 years the 16710 production was split between three different colors schemes (red/black, blue/red, and all black), one must certainly conclude that a “true” Pepsi 16710 is a relatively rare bird.

Brock Stevens - U.S. Navy Diver, Photographer & Watch Enthusiast @deepsea.edc

Rolex Sea-Dweller 1665 (from the US Navy SEALAB Era)

Price: $65K+

(Photo Credit: Bob’s Watches)

As a Navy Diver, the Rolex “Red Line” Sea-Dweller from the SEALAB era is my grail watch because of its importance to U.S. Navy Diving history. In a series of deep saturation dives conducted at the U.S. Navy Experimental Diving Unit prior to SEALAB 3, divers found that their watch crystals were literally popping off during decompression as helium had accumulated inside the case. 

The solution of a one-way valve to release the trapped gas was a simple idea by Navy diver and aquanaut Bob Barth, which Rolex implemented in what has now become the ubiquitous helium escape valve. For me, that’s what sets the Red Line Sea-Dweller apart. It is the result of a solution to a problem and of a need to create a tool that is the embodiment of the Use Your Tools ethos of Watches of Espionage.

J.R. Seeger - Archeologist, Paratrooper, Intelligence Officer, & Novelist. Latest Book: Remains of a Spy 

A Panerai Radiomir issued to the San Marcos Battalion of the Italian Navy special operations unit, Decima Flottiglia MAS. 

Price: A recent example sold for $104,500. 

(Watch Photo Credit: Oliver Smith Jeweler)

After Rome fell and the Italian government surrendered to the Allies, most of the Decima MAS retreated with the Germans behind the Gothic Line and conducted anti-resistance operations in the Italian Alps. Instead, the San Marcos Battalion troops opted to work with the allies, specifically working with OSS/Operational Groups (OSS/OG) and OSS Maritime Unit (OSS/MU) on the east coast of the Italian peninsula. The Radiomir was the issued watch to every member of the Decima MAS, but a Radiomir that served both the Fascists and US special operations forces would be a rare watch worthy of the title “grail." My grail would be a working version of the watch, and I would wear it.

Nacho Conde - Writer, Photographer, Head of Content/Managing Editor at Fratello, & the Host of the Fratello Talks Podcast. @nachoconde

Vacheron Constantin Overseas "Everest" Dual Time LE

Price: These days, they go for upwards of $100k. 

(Photo Credit: Revolution)

First seen as a prototype on the wrist of NatGeo photographer, mountaineer, and certified badass Cory Richards, this spec of the VC Overseas Dual Time is a watch I’ve lusted after since I first read about it. The watch feels like a glitch in the matrix: something that shouldn’t exist, where there was every chance for it to get scrapped along the way, yet somehow it stubbornly powered through into existence. It’s a baffling creation from a brand primarily known for opulent luxury pieces and hyper-complicated pocket watches the size of softballs.

The 41mm titanium case, bead-blasted crown and bezel, and grey grainy dial with orange accents make for a perfect recipe. A watch born from the mind of a man who risked life and limb seeking a new route to the summit of the planet’s highest peak without supplementary oxygen is a tool that doesn’t just beg to be used; it inspires its wearer to do so.

(Photo Credit: Revolution)

It’s a grail for two good reasons. First, only 150 were made and sold out long ago. Second, the few that appear on the secondary market command three to four times the already grail-worthy retail price, tortuously keeping it a lucky lottery win or a spare kidney out of reach.

Asha Wagner - Fire Captain & HazMat Specialist @wildlander6

MN-Issued 1976 Tudor Submariner 9401 (with a Destro Crown?)

Price: $30k plus. 

(Photo Credit: Buland & Sons)

I love a good watch that represents ingenuity, has lived a little, and has stories to tell. Therefore, the watch I’m picking for my grail is an issued 1976 Tudor 9401 Snowflake MilSub. Prior to the Snowflakes, Tudor Subs used the Rolex Mercedes handset. The snowflake handset and dial were born from pure utility, at the request of divers who needed more legibility in murky underwater scenarios. The Snowflake design was implemented because it allowed the hands and dial to hold more lume. This in turn made them more legible in adverse conditions. 

The snowflake MilSubs debuted on the Tudor 7016 and 7021 watches in the late 1960s. In 1976, Tudor introduced the 9401, which had an upgraded movement that allowed for hacking seconds, which was another mission-focused upgrade. It just so happens that 1976 is my birth year. In addition to this, the watches were generally issued without straps. The soldiers often used parachute webbing to form makeshift straps. I’m a former Forest Service Helicopter Rappeller and a member of the Triple Nickles Parachute Infantry Association, so the parachute webbing is another fun fact that just tickles me.

(Photo Credit: Bulang & Sons) 

With the watch being military-issued, there’s a very good chance the watch was not babied, let alone kept in a safe. I’d love to have a watch that’s been around as long as I have, been through a fair bit, and has a few scars to prove it. Ghost bezel and a left-handed “Destro” crown (available as a special order for the Marine Nationale) are always a plus.

Rob Huberty - Former Navy SEAL & Co-Founder/COO of ZeroEyes 

Paul Newman Rolex Daytona & MB&F Sequential EVO

Price: $600k for the Paul Newman & $210k for the MB&F. 

(Photo Credit: Rob Huberty)

If the lotto hits, I am going all in on two watches. I love vintage Rolex, but I am afraid of fakes or Frankenwatches built with some real and some fake parts. The Paul Newman Daytona has been a dream for me for many years. I love mechanical chronographs. Unfortunately, really using a vintage chrono and getting it wet are probably not in the cards, even with an unlimited bank account. My modern alternative is an MB&F Sequential EVO. The watch is a handmade, alien work of art that feels like a pocket universe from the Men in Black series. It has two chronographs and is dive-able. Maybe I don’t need to live in a house if I can time two things at once, right? 

Final Thoughts 

In the end, the watches we chase, whether they’re obscure military-issued relics with salt still trapped in the bezel, shadowy prototypes that survived by accident, or high horology pieces with seemingly impossible complications that make no practical sense at all, say less about price tags and more about the people we are. For us, a “grail watch” isn’t just rare; it’s aspirational, a mirror reflecting our experiences, values, and the stories we hope link to the watch over time.

And while most of these references will remain forever out of reach, as they say, sometimes it’s the journey and not the destination. It reminds us why we fell in love with watches in the first place: not for what they’re worth, but for the worlds they open, the history they carry, and the adventures they quietly dare us to pursue.

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