Rolex, A Love-Hate Relationship — Part II

One Year Later - Selling My “Bruce Wayne” Rolex GMT Was the Best (Watch-Buying) Decision I Have Made

Sitting in a cafe in the old town of Geneva, I explained my predicament to veteran vintage watch dealer Skip Powell and a former Army Special Forces officer turned watch collector (alias De Tempore Liber). The year prior, I had purchased a new Rolex GMT-Master II with a black and grey bezel, dubbed the "Bruce Wayne" by watch nerds. Despite my best efforts to appreciate it, it had sat mostly in the safe, and I wasn't sure what to do with it. Should I sell it and buy a vintage Rolex or a military-issued Tudor Submariner? Or should I hold onto it in hopes that I would appreciate it more later?

If you aren't into watches, the whole premise sounds absurd. Three grown men sipping Negronis in Geneva debating the fate of a watch worth as much as a car.

My Rolex GMT-Master II “Bruce Wayne” - Reference 126710GRNR

In April 2025, I published what became one of our most widely read pieces, a candid account of buying my first modern Rolex and the unexpected disenchantment that followed. The piece touched a nerve. Nearly 100 comments, countless messages, and enough shared frustration to confirm that this was not just my experience.

You can read the full piece HERE, but the short version is this: the Bruce Wayne is an exceptional watch, but purchasing a modern Rolex is a deeply compromised experience. The waitlist is largely a myth, the allocation process rewards relationships over merit, and I left the boutique feeling hollow about spending $11,000 on something I had been permitted to buy rather than something I had earned the right to own. The love for what Rolex represents, tool watches for adventurers, explorers, and warfighters, sits in constant tension with the reality of what buying (and wearing) a Rolex today actually looks like. 

I am a GMT guy to the core, and despite what the haters will say, the Bruce Wayne is a genuinely exceptional watch, at least when it’s paid for at retail with no grey market games. But over twelve months in, it still felt cold on the wrist. I had worn it on and off, appreciated it intellectually, and never once felt the connection I expected (hoped). The only story I could contrive for it was the idea of putting it away and giving it to my son when he graduates college. That felt like the right story for a watch that hadn't earned one yet.

For Skip and the anonymous SF soldier turned watch nerd, it was easy. Sell the watch and buy something I will appreciate now: a vintage military-issued Tudor or an older GMT. In reality, it was a simple decision, but sometimes you need the boys to point out the obvious.

The Trade, Arbitrage, & the Grey Market Reality

W.O.E.’s new Rolex GMT-Master reference 16700 (Photo Credit: Wind Vintage)

A few weeks after Geneva, I found myself scrolling through watch dealer sites and came across an exceptional “GMT-Master,” reference 16700 with an all-black bezel on Wind Vintage. 

The math was straightforward and, if I am being honest, a little uncomfortable. I had paid $11,000 retail for the Bruce Wayne. Its current grey market value sat somewhere between $18,000 and $20,000. The all-black bezel GMT-Master, in exceptional condition at nearly three decades old with original bracelet and caseback sticker intact, was listed at under $15,000. After a short text message exchange, the watch was en route to me, along with a prepaid label to send my full-set Bruce Wayne to him.

The grey market premium on the modern Rolex that I had been permitted to buy essentially funded a superior, more interesting, and more historically significant watch with money left over. That is either a ringing endorsement of the neo-vintage market or a damning indictment of current Rolex allocation practices (probably both).  

I had written in Part I that flipping a Rolex felt like a betrayal of principle. What I had not fully considered was that the grey market arbitrage built into the modern Rolex buying experience makes every retail customer a potential flipper whether they intend to be or not. Whether using the sale to fund another watch purchase, or just make a few thousand dollars, the system creates the incentive. I simply redirected mine toward something I actually wanted. It would have been irrational NOT to sell it.

W.O.E.’s new Rolex GMT-Master 16700.  (Photo Credit: Wind Vintage)

Neo-Vintage - The Golden Era

“Neo-vintage” is really just a fancy term watch collectors coined for watches manufactured from the mid-1980s through the early 2000s. Old enough to retain the drilled lugs, aluminum bezel inserts, and honest tool watch proportions of the classic era, but new enough to carry a robust modern movement and serve as a watch for genuine daily wear.

In my opinion, this period represents the best of Rolex. As recently as the late 1990s, Submariners and GMTs were available at military post-exchange stores, purchased by soldiers and sailors who wanted a capable tool watch at a (relatively) reasonable price. While the transition to quartz watches was all but complete, “neo-vintage” watches were still often used as tools and not quite yet fashion statements.

Neo-vintage is also, at the moment, one of the more rational purchases in the Rolex ecosystem, assuming you can find a decent example from a reputable dealer. 

W.O.E.’s Rolex GMT collection presale.

Selling vs Trading

In my piece on how to buy a vintage military-issued watch (READ HERE), I wrote that I prefer buying from collectors rather than dealers. Vintage Rolex is the exception. These watches are a commodity and a wilderness of mirrors, and if something goes wrong, I want someone to call who has both the expertise and the incentive to make it right. I could have likely extracted more value from a private sale of the Bruce Wayne, but the added complexity and risk were not worth it in my mind. 

Wind Vintage publicly advertises a ten percent commission on watch sales, which, in the context of a transaction this size, and with money that was essentially found, felt like a reasonable price for peace of mind and security. The trade made the whole process clean and straightforward, and no money ever left my account. Sometimes simple is the right answer.

Rolex GMT-Master 16700

(Photo Credit: Wind Vintage)

When I was working in Africa, I had a friend who religiously wore a black bezel Rolex GMT. He purchased it before a deployment to Yemen with JSOC as an “Escape and Evasion” Rolex and wore it everywhere. I always envied his one-watch collection (and his Land Rover Defender). In contrast to the Pepsi, the black bezel is a more subtle model. To the untrained eye, the red hand was the only indication it was a GMT, more likely to be mistaken for a Submariner.

The GMT-Master I ended up with was exceptional. Dating to circa 1999, the case appears unpolished, and the caseback sticker remains intact, a remarkable detail on a 25-year-old piece. The specific detail that separates this example from the majority of 16700 production is the “Swiss Only” dial. Earlier examples carried the full "Swiss Made" text at six o'clock on the dial, while Swiss Only references omit the "Made" designation, a subtle variation that commands a premium among serious collectors and represents one of the last dial configurations before the reference was discontinued in 1999. (Full disclosure, these small details don’t really excite me, but they are interesting to learn.)

It is worth understanding the distinction between the 16700 (GMT-Master) and the 16710 (GMT-Master II). The GMT-Master is powered by the caliber 3075, while the GMT-Master II uses the more capable 3185 caliber with an independently settable hour hand. Both were available in black and Pepsi bezel configurations, but the 16710 also offered the Coke variant and a longer production run from 1989 to 2007. I already own a Coke 16710, so this black bezel 16700 was a deliberate complement rather than a duplicate.

Drake’s Ice Gradient Daytona is a pièce unique valued at an estimated $5M and a troubling indicator of where modern Rolex’s priorities lie. (Photo Credit: Instagram)

Final Thoughts

Just last week, Rolex commissioned a one-of-one diamond and sapphire Daytona for rapper Drake, a pièce unique valued at an estimated $5 million. I am far from a Drake hater (that Hotline Bling song is cool), but this is the latest signal of where the brand's priorities now sit. The “iced out” Daytona sits in stark contrast to the Rolex of Mercedes Gleitze swimming the English Channel, Edmund Hillary summiting Everest, or Jacques Piccard descending to the deepest point in the ocean. It is a marketing asset for a rapper's album cycle announced on Instagram with the instruction not to ask your local jeweler to recreate it. 

The same brand that built its reputation outfitting British commandos, Antarctic expeditions, and deep-sea divers is now producing bespoke gem-set chronographs to commemorate Billboard chart positions. For those of us who came to Rolex through its tool watch heritage, the distance between that tradition and the Ice Gradient Daytona is not just aesthetic. It is a statement about who Rolex believes its customer is now, and it is not me.

The good news is that the neo-vintage market still offers a direct connection to that heritage, at a fraction of the cost of a modern allocation and without the indignity of a waitlist. I plan to wear this one for the next decade, build memories with it, and ultimately give it to my son when he (hopefully) graduates college.

Sometimes the best decisions are the simple ones: Sell the watch you do not love, buy the one you do. The boys in Geneva were right.

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