Two of Rolex’s most famous faces are putting the brand’s most coveted watch to work for a good cause. Roger Federer and Leonardo DiCaprio, both longtime Rolex Testimonees, have joined the brand for the Four Seasons auction, a sale of four unique, gem-set Cosmograph Daytonas at Phillips in London on September 28. Every dollar raised will go to two causes close to the pair: children’s education and the planet.
Roger Federer and Leonardo DiCaprio join the Four Seasons auction at Phillips on September 28: four unique gem-set Cosmograph Daytonas.

The proceeds are split between the two men’s foundations. The Federer Foundation, established in 2003, works to give children in Southern Africa and Switzerland access to education. Re:wild, co-founded by DiCaprio alongside a group of conservation scientists, restores and protects the natural world in partnership with Indigenous Peoples, local communities, and on-the-ground organizations. The pairing, tennis’s greatest champion and Hollywood’s most visible environmentalist, gives the sale an unusually broad philanthropic reach.

The watches themselves are extraordinary, even by Daytona standards. Each of the four is a one-of-a-kind, fully gem-set Cosmograph Daytona built around a natural-stone dial and a different precious metal, and each interprets a season. Spring is an 18K white gold model with a chrysoprase dial and a bezel of purple sapphires. Summer, in Everose gold, pairs a turquoise dial with pink sapphires and ruby-heart counters.

Autumn, in yellow gold, sets green tourmalines against a mookaite dial. And Winter, the most precious of the four, is cased in 950 platinum with a blue opal dial, diamond hour markers, and a bezel of sapphires that fade from blue to fuchsia. All four carry lugs and crown guards set with 54 brilliant-cut diamonds.

The gesture is notable. The Cosmograph Daytona remains the most sought-after watch Rolex makes, and gem-set, one-off examples almost never come to market, let alone with provenance tying them to two of the most recognizable people alive. Rolex has a long history of philanthropy through its Testimonees, but four unique Daytonas offered together, for causes as different as education and rewilding, is a rare move, and one likely to draw serious bidding when the hammer falls on September 28.
