These Are the Ultra-Exclusive Rolex Watches That Money Can’t Buy

You know you want one.



Purchasing a Rolex has long been a rite of passage for successful men everywhere, often the first step toward building a collection worthy of passing down. But an even more select group wear the rarest Rolexes of all on their wrists—watches no amount of money can buy. 

These are the world’s top guns in gentlemanly pursuits like sailing, motor racing, exploring and equestrianism, who have “won the watch” in competition, purely on skill and merit.


From a distance, the timepieces might not look that different from what you’d find in a high-end jewelry shop, but turn the watch over and its true character is revealed: the official engraving on the caseback, and especially the magic word, “Winner.” 

These prizes are presented in Rolex’s signature dark green leather box, customized with scenes of the sport in question. But the exhilaration comes from the owner’s knowledge of what’s discreetly pressed up against the top of his or her wrist. 


The watch isn’t the kind of thing you’d ever sell; its value as an heirloom is worth more than any monetary reward, but just to give you an idea: one Rolex chronograph presented to racecar drivers in the 1940s now brings in over $1 million at auction. 

Who’s to say what a modern example might be worth in 75 years. If it ever belonged to a famous driver the sky’s the limit.


Rolex’s ties to the world of sports go deep, part of the brand’s mission to support “individual excellence and the quest for perfection.” They were, after all, designed as the world’s first sports watches when Hans Wilsdorf established the company in 1905. 

These days Rolex awards watches in a range of sporting activities and events. Drive the winning car in the legendary Rolex 24 at Daytona race in Florida, held since 1966 and one leg of the “triple crown” of endurance racing, and you’ll receive the equally iconic timepiece named for it: a Rolex Daytona Cosmograph, the most enviable of all sports watches, engraved with the year and the famed Rolex 24 at Daytona logo. 


In other upscale sports like sailing, tennis and equestrian events, prize Oyster Perpetual Rolexes make top-drawer competitions that much more intense, like the venerable New York Yacht Club’s annual Regatta and Race Week in Newport, Rhode Island, where the Submariner Date is up for grabs. 

The winner of the Rolex Kentucky Three-Day Event, one of the most prestigious equestrian competitions in the country, takes home a watch every bit as coveted as the trophy itself, the timeless and elegant Datejust.


Rolex also awards watches to the Rolex National Geographic Explorer of the Year, who receives the Explorer, a model worn by Sir Edmund Hillary when he climbed Everest, and to its Yachtsman of the Year, who gets a very special Yacht-Master. The 2015 recipient, Steve Benjamin, compares winning his watch to medaling at the Olympics—which he’s also done.

As New York Yacht Club’s Vice Commodore Phil Lotz puts it, winning a Rolex “is a universally understood emblem of significant accomplishment.” Worth, in the case of sailing, at least, spending millions on a yacht and crew just to get one.