How much are you prepared to invest for a wristwatch? For a chosen few with deep pockets, the figure can soar into the millions. However, there exists a watch that cannot be purchased, only earned: the uniquely engraved Rolex Daytona, exclusively awarded to the victors of the Rolex 24 at Daytona or the 24 Hours of Le Mans. Athletes dedicate their lives to these races, yearning for that hard-to-achieve triumph—and a brand-new watch.

At the 2024 Rolex Monterey Motorsports Reunion, held at WeatherTech Raceway Laguna Seca during Monterey Car Week, Motor1 had the opportunity to interview two racing icons: Formula 1 champion Jenson Button and sports-car racing legend Hurley Haywood. Both are Rolex ambassadors, keen to share their insights on the appeal of these race-won watches and their significance to the motorsport community. Rolex became the title sponsor of the 24 at Daytona in 1992, and has since awarded prize watches to the winners of each class. (Since 2001, Rolex has also presented commemorative watches to the winners of the 24 Hours of Le Mans, but only to the overall victor.)

"They're a trophy you can wear to the bar," remarked James Stacey, lead editor at watch aficionado publication Hodinkee. Typically, the race-winner watch is a Rolex Daytona, similar to those available to retail customers, though certain years feature unique color schemes. "There are individuals who spend millions to secure one of these watches," Stacey noted. "They could easily have purchased something very similar at the store, even at a premium." But that wouldn't carry the same significance.

Hurley Haywood possesses five watches commemorating his five overall victories at the Rolex 24 at Daytona. These were not awarded in chronological order. "The first watch I received for winning the race was in 1991," Haywood recounted to Motor1. "But that was my fifth win." 1991 marked the first year Rolex distributed Cosmograph Daytonas on the podium, and Haywood's Joest Racing teammates each received a watch celebrating their victory in a Porsche 962 C. Haywood received a bit more.

"Roland Puton, the president of Rolex, said, we're going to backdate it," Haywood explained to 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." Besides being America's premier endurance racing driver, Haywood is a genuine watch enthusiast. There's no one more qualified to articulate the allure of a race-winner Rolex.

"That watch symbolizes why everyone in the world wants to win that race," he said of the Daytona prize watch. "Many of the guys are very wealthy, they can buy whatever they want. But winning that watch, for that race, is the one they desire. It surpasses any trophy." 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 features a personal engraving from Rolex on the back, making it a unique piece.

In the frenzied world of watch collecting, some have boldly attempted to purchase one of Haywood's trophy watches. "I've been offered exorbitant sums for some of the watches I own," he told Motor1. "Insane. No matter how much they offer, it's a personal matter—I won't sell any watches I won."

Formula 1 champion, SuperGT champion, and current World Endurance Championship competitor Jenson Button took a break 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 candid about the watches absent from his collection. "I've never won a Rolex watch," Button confessed to Motor1. "I've only ever competed in two races where I could. 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 good enough to compete upfront. 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 participated in an astonishing array of motorsport series, from Trophy Trucks to period-correct races at the Goodwood Revival. Victory at Daytona remains on his agenda.

"Everyone adores 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 crazy, the amount of money people spend to win the race [just] to win the Rolex. I know drivers who 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." Another Cosmograph Daytona in his collection has personal motorsports provenance. Button bought it as a gift for his father, John Button, and inherited it upon his father's passing.

"Rolex has been involved in 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 remain with Jota for 2025—which would give him another chance at winning the 24 Hours of Le Mans, and the Rolex that accompanies an overall victory at the renowned endurance race.

"That's always the ideal," Button told Motor1. "To win a Rolex."