What It Means to Win a Rolex Daytona

What’s the most you’re willing to spend to get a wristwatch? For a select group of well-heeled people, that number can reach millions.

But there’s one watch that can not be bought, only earned: The specially engraved Rolex Daytona awarded exclusively to the winning drivers of the Rolex 24 at Daytona or the 24 Hours of Le Mans. Competitors spend a lifetime preparing for these races, hoping for that elusive victory—and a brand-new watch.

Against the backdrop of the 2024 Rolex Monterey Motorsports Reunion, held at WeatherTech Raceway Laguna Seca during Monterey Car Week, Motor1 spoke with two living legends of racing: Formula 1 champion Jenson Button, and sports-car racing legend Hurley Haywood. Both drivers are Rolex ambassadors, eager to discuss the allure of these race-won watches and what they mean to the motorsport community.

Rolex became the title sponsor of the 24 at Daytona in 1992, and since then has given prize watches to drivers who take first place in each class. (Since 2001, Rolex has also given commemorative watches to winners of the 24 Hours of Le Mans, but this prize is reserved for the overall winner.)

“They’re a trophy that you can wear to the bar,” said James Stacey, lead editor at watch enthusiast publication Hodinkee. Usually, Stacey said, the race-winner watch is a Rolex Daytona, similar to what’s available to retail customers, though some years feature unusual color combinations.

“There are people who spend millions of dollars to win one of these watches,” Stacey said. “They easily could have just bought something very similar at the store, even paying way over retail.” But that wouldn’t have the same meaning.

Hurley Haywood has five watches commemorating his five overall victories at the Rolex 24 at Daytona. They weren’t exactly awarded chronologically.

“The first actual watch I got for winning the race was 1991,” Haywood told Motor1. “But that was my fifth win.” 1991 was the first year that Rolex gave out Cosmograph Daytonas on the podium, and Haywood’s Joest Racing co-drivers each got a watch commemorating their victory in a Porsche 962 C. Haywood got a little extra.

“Roland Puton, who was the president of Rolex, said, we’re going to backdate it,” Haywood told Motor1. “I’d won five [Rolex 24 at Daytona] races up to that point, he backdated it four times, so I got five watches on that deal.”

In addition to being America’s greatest endurance racing driver, Haywood is a true watch connoisseur. There’s nobody on earth more qualified to explain the appeal of a race-winner Rolex.

“That watch represents why everybody in the world wants to win that race,” he said of the Daytona prize watch. “A lot of the guys are very wealthy, they can buy whatever they want to. But winning that watch, for that race, is the one they want. It beats any trophy.”

“The first actual watch I got for winning the race was 1991… But that was my fifth win.”

Haywood’s watch collection includes another Daytona, a gift from Rolex commemorating his role as Grand Marshal of the 2013 running of the 24-hour race. Like each of his race-winner watches, it bears a personal engraving from Rolex on the back, making it an irreplaceable one-of-one. In the crazy world of watch collecting, some folks have been brazen enough to attempt to buy one of Haywood’s trophy watches.

“I have been offered obscene amounts of money for some of the watches that I have,” he told Motor1. “Crazy. No matter how much they would give me, it’s just a personal thing—I’m not going to sell any watches that I won.”

Formula 1 champion, SuperGT champion, and current World Endurance Championship competitor Jenson Button took time away from racing his 1952 Jaguar C-Type at the Rolex Monterey Motorsports Reunion to chat with media guests of Rolex. Despite being a Rolex Testimonee since 2021, Button was characteristically forthright about the watches missing from his collection.

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“I’ve never won a Rolex watch,” Button told Motor1. “I’ve only ever done two races where I can. I did Daytona this year, first time—finished on the podium, which was good. I’ve raced at Le Mans three times. This is the first year where we had a car that was good enough to fight in front. But we finished 9th on the lead lap.”

A race-won Rolex Daytona currently eludes the F1 champ.

Since retiring from full-time Formula 1 racing at 36 in 2016, Button has competed in an astounding variety of motorsport series, ranging from Trophy Trucks to period-correct races at the Goodwood Revival. Victory at Daytona is still on his radar.

“Everyone loves racing at Daytona,” he told Motor1. “They want to win because they want to win, but there’s so much excitement about winning a Rolex Daytona at Daytona. People come and do a one-off race there, like I did, because you want to win a Rolex Daytona. It’s nuts, the amount of money that people spend to win the race [just] to win the Rolex. I know drivers that have four or five, and I’m like, ‘I hate you.’”

Button owns a steel Daytona, a gift to himself upon starting his Formula 1 career in 2000 at age 20.

“Moments in your life, moments in time,” he said. “It’s like music, perfume—for me, watches bring me back.”

“Everyone loves racing at Daytona… They want to win because they want to win, but there’s so much excitement about winning a Rolex Daytona at Daytona.”

Another Cosmograph Daytona in his collection has personal motorsports provenance. Button bought it as a gift for his father, John Button, then inherited it when the former rallycross driver passed away.

“Rolex has been around motorsport for so long,” Button said. “I think the connection for racing drivers is that we love the mechanical aspect of it.” He mentions his 1952 Jaguar, originally owned by Juan Manuel Fangio. “That C-Type, you’ve got a real connection to it. You’ve got to heel-and-toe, you’ve got to get the right revs, all that sort of stuff is super cool. And I feel that a mechanical watch is the same. The precision is insane, and that’s what I think we love.”

Button has three more races this season driving the No. 38 Porsche of Hertz Team Jota in the FIA World Endurance Championship. As of now, he plans to stay with Jota for 2025—which would give him another shot at winning the 24 Hours of Le Mans, and the Rolex that comes with an overall victory at the legendary endurance race.

“That’s always the ideal,” Button told Motor1. “To win a Rolex.”

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