Leonardo DiCaprio & Roger Federer Just Wore Two Of The Rarest, Most Expensive Rolex Daytonas … from Maxim Jared Paul Stern

Courtesy Bob’s Watches

Being a Rolex brand ambassador, or “testimonee” as the watchmaker calls them, certainly has its privileges. In addition to a substantial paycheck, the anointed get access to the rarest of the rare “off-catalog” Rolex watches that are never made publicly available—often at a discount or even for free. If getting paid to wear an impossible-to-obtain Rolex sounds like the cushiest gig imaginable, only the extremely accomplished, mostly from the world of elite sports, ever get offered the opportunity.

Several months ago however, Rolex signed its first-ever actor, Leo DiCaprio, to join their testimonee ranks. And the superstar actor has wasted no time wearing the most exclusive Rolex timepieces in the world, including the brand new Land-Dweller, which was introduced earlier this year and is extremely difficult to get your hands on.

(Pascal Le Segretain/Getty Images)

At the recent premiere of his new hit movie One Battle After Another, which recently reached the $100 million box office mark, DiCaprio just wore his most impressive Rolex piece to date, the gorgeous Daytona “Le Mans” in white gold. Back in August we reported that the off-catalog “Le Mans” is the “coolest watch money can’t buy,” destined to be a future holy grail for collectors.

Courtesy Bob’s Watches

Other celebs who have been spotted wearing it include Tom Brady (white gold), Mark Zuckerberg (yellow gold), Michael Jordan (white gold), Mark Wahlberg (white gold), LeBron James (yellow gold), John Mayer (white gold), Lionel Messi (white gold), Orlando Bloom (white gold), Kevin Hart (yellow gold), Tommy Hilfiger (white gold), and Sir Jackie Stewart (yellow gold).

Left to right: Andy Murray, Federer, Rafael Nadal and Novak Djokovic during a promo photo shoot for the 2022 Laver Cup.
(Credit: © Clive Brunskill/Getty Images for The Laver Cup)

It might sound like a hard act to follow. But leave it to tennis legend Roger Federer, another longtime Rolex testimonee, to ace it in one. Federer already has a “Le Mans” of his own, but at the recent Laver Cup tennis tournament in San Francisco, he showed up with an even more unobtainable Daytona strapped to his wrist: the so-called “Blue Sapphire.”

Valued at approximately $1.5 million, only a few examples are known to exist, and they are rarely if ever seen. The eye-popping timepiece features an 18K white-gold case, a natural silver obsidian dial, and a bezel set with 36 baguette-cut blue sapphires and 54 brilliant-cut diamonds. It isn’t as flashy as the better known “Rainbow” Daytona because its color scheme is relatively muted. But as a flex it blows the “Rainbow” away.

(Watches & Wonders)

World No. 1 tennis player Carlos Alcaraz, a more recent Rolex testimonee who played at the Laver Cup, wore a pretty rare off-catalog Daytona himself with a Tiffany-style blue dial. But Alcaraz was visibly stunned by Federer’s even more exalted “Blue Sapphire” stunner, which served as a timely reminder that he has a ways to go before becoming a true legend like the Swiss Maestro.

Courtesy Bob’s Watches

“The ‘Le Mans’ Daytona is an absolute winner,” says Paul Altieri,  founder and CEO of Bob’s Watches, who is one of the world’s top Rolex collectors. “It’s my top pick to become as iconic as the ‘Paul Newman’ Daytona in the years to come.” Federer’s “Blue Sapphire” Daytona meanwhile “is one of only a few examples Rolex will ever make,” he says. “It might be more rare, but it’s almost an oddity or a novelty piece, with an outlandish price to match.”

The most exciting prospect for collectors, however, Altieri says, is the possibility that one or both of the watches could come up for sale or auction some day. “The provenance of these pieces would put them into the stratosphere,” he notes. “Rolex would no doubt like to acquire them for its own private collection. But they’re going to face fierce bidding from some collectors I know whose pockets are almost as deep.”

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