Biography & Early Wealth Journey

Auction house Sotheby's is estimating that each timepiece will get anywhere from $500,000 to $1 million, but according to experts in the field, they could be worth significantly more than $1 million each.

Whether he knew it or not, once Newman was photographed wearing a watch on his wrist, that watch became exponentially more valuable than it would otherwise be. And his lifelong love of Rolexes has led to a strong association between himself and the brand, particularly the Daytona model he had a special affinity for. According to New York City watch dealer Andrew Shear, Newman was a pioneer in the field of watch collecting itself: "We can tie vintage-watch collecting, vintage-Rolex collecting to him," Shear said.

Back in 2017, another Rolex Daytona that was once owned by Newman, reference 6239, sold for nearly $18 million, making it the most valuable such watch he ever owned, not to mention the most expensive Rolex ever sold publicly. Not a bad sum for a watch that his wife Joanne Woodward paid around $300 for sometime in the 1960s, having it inscribed on the back with "Drive Carefully Me." That was around the time Newman was first getting serious about stock car racing, another lifelong passion of the actor's.

Primary Income Streams & Multi-Million Contracts

ISC Archives/CQ-Roll Call Group via Getty Images

It was Newman's racing that got him the first of the two watches set to be auctioned off in June. In 1995, he won a 1993 Rolex reference 16520 "Zenith" Daytona at the 24 Hours of Daytona Race in Daytona Beach, a race he won when he was 70 years old. Then, in 1999, he donated the watch to a charity auction (where it fetched the relatively meager sum of $39,000), but at some point after that the watch was quietly purchased back by Newman or someone close to him.

The second watch was purchased by Woodward as a gift for Newman, echoing the watch she'd given him many years earlier. It's a 2006 white-gold reference 116519 Daytona with the inscription "Drive Very Slowly Joanne."

Newman's love of the Rolex Daytona timepiece was well known to friends. Not only did he popularize the watch among watch collectors (contributing to its high value today), but he was known to place bets with guests that his own watch could keep better time than theirs. So it's a very long association leading to these two watches being auctioned this summer.

Trending Wealth Dossiers: