THE WORLD’S MOST FAMOUS ROLEX

The story of Paul Newman’s Rolex Daytona and the guy who sold it for $17 million

If your daughter’s boyfriend spent the summer at your cottage and helped you rebuild a treehouse, you might reward him with a cold six-pack and a pat on the back. If you’re Paul Newman, however, you give him the world’s most valuable Rolex. The watch in question is a 1960s Cosmograph Daytona reference 6239, and it set a new record when it sold for $17,800,000 at a Phillips auction in October. Must have been some treehouse.

An enthusiastic race car driver, Newman received the Daytona — a watch designed specifically for timing car races — as a gift from his wife Joanne Woodward, who engraved “Drive Carefully, Me” on the back, a gentle reminder that even Butch Cassidy wasn’t invincible. Newman was photographed wearing the watch regularly over the next decade as he competed in high-profile races, including a second-place finish at the 24 Hours of Le Mans.

Thanks to a combination of limited production, unusual details on the dial, and its association with the famous actor, the so-called “Paul Newman” Daytona became one of the most collectible timepieces in the world. Worth far more than similar Daytonas from that era, they regularly fetch over $100,000 at auction. Newman’s own watch, of course—and the bragging rights that come with it — is worth far more.

Although his relationship with Newman’s daughter Nell ended in 1993, James Cox, the treehouse-building boyfriend and owner of the record-setting Daytona, remains the treasurer of the Nell Newman Foundation. Cox will donate a portion of the watch sale to the foundation, which seeks to continue Paul Newman’s philanthropic legacy. Regardless of who ends up owning his watch, Newman would certainly be happy to see his act of generosity begetting another, with interest.