How much are you willing to invest in a wristwatch? For a privileged few with deep pockets, the figure can soar into the millions. However, there exists a watch that cannot be purchased but must be earned: the uniquely engraved Rolex Daytona, exclusively awarded to the victors of the Rolex 24 at Daytona or the 24 Hours of Le Mans. Aspiring to claim this prestigious timepiece, racers dedicate their lives to these competitions.

During the 2024 Rolex Monterey Motorsports Reunion at WeatherTech Raceway Laguna Seca, Motor1 had the privilege of interviewing two racing icons: Formula 1 champion Jenson Button and sports-car racing legend Hurley Haywood. Both are Rolex ambassadors and were keen to share their insights on the significance of these race-won watches within the motorsport community. Rolex became the title sponsor of the 24 at Daytona in 1992, and has since presented winning drivers in each class with prize watches.

James Stacey, lead editor at Hodinkee, described these watches as trophies one can wear to the bar. Typically, the race-winner watch is a Rolex Daytona, similar to those available in stores, albeit with unique color schemes in some years. Stacey noted that while some enthusiasts spend millions to secure one of these watches, they could easily acquire a similar model at retail, albeit at a premium. However, the emotional value of winning one is irreplaceable.

Hurley Haywood, with five overall victories at the Rolex 24 at Daytona, owns five commemorative watches. His first watch, received in 1991, was backdated by Rolex to reflect all five of his wins. Haywood, a true watch aficionado, underscored the allure of a race-winner Rolex, stating that it surpasses any physical trophy.

Jenson Button, despite his illustrious career, has yet to win a Rolex watch. He has participated in races where such a prize was possible, including Daytona and Le Mans, but has not yet secured victory. Button, a Rolex Testimonee since 2021, expressed his desire to win a Rolex Daytona, highlighting the intense competition and financial stakes involved in these races.

Button, who owns a steel Daytona gifted to himself at the start of his Formula 1 career, cherishes the personal connections his watches hold. He also inherited a Cosmograph Daytona from his father, John Button, adding to the sentimental value of his collection. Button appreciates the mechanical precision of Rolex watches, likening it to the intricacies of racing.

With plans to continue racing with Jota in 2025, Button remains hopeful of winning the 24 Hours of Le Mans and the coveted Rolex that accompanies an overall victory. His passion for racing and collecting Rolex watches underscores the deep-seated connection between motorsport and horology.