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The forthcoming auction at Phillips in New York City is aptly-titled “GAME CHANGERS” because many of the timepieces were worn by individuals who have — and continue to — imbue a legendary status. The global platform, best known for buying and selling 20th and 21st century art and design, also has a particular reputation for making horology feel inclusive — even if the prices are exorbitant — by using strong storytelling to spark general interest.

For example, in 2017, there was a prominent narrative attached to the sale of Paul Newman’s Rolex “Paul Newman” Daytona reference 6239. At the time, the $17,752,500 price tag was the ­­highest result ever achieved for a wristwatch at auction. While the piece itself was a perfect combination of celebrity culture mixed with Rolex’s craftsmanship, Phillips was able to push the price so high because wearing a watch is just as much about its lineage.

With “GAME CHANGERS” scheduled for December 10, we reached out to Paul Boutros, Phillips’ Head of Watches, Americas, to get a peak behind the curtain. Chock full of rare brands like Rolex, Patek Philippe, A. Lange & Söhne, Audemars Piguet, Vacheron Constantin, Omega, TAG Heuer, Jaeger LeCoultre, Breitling, Urwerk, Philippe Dufour, F.P. Journe, and Richard Mille, “GAME CHANGERS” promises to be the Super Bowl for watch collectors.

Here’s what you need to know about the Rolex lot.

Rolex Jack Nicklaus Rolex Day-Date

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Boutros considers Jack Nicklaus’ Rolex Day-Date to be, “possibly the most viewed wristwatch ever when you consider that it was worn for 50 years by the greatest golfer of all time around the world in trophy after trophy.”

Nicklaus first received the watch as a gift from Rolex in 1967. In 2017 — when he considered what to do with the watch — he realized that his kids and grandkids probably wouldn’t wear it. As a result, he decided to partner with Phillips to donate the proceeds to his preferred charity, the Nicklaus Children’s Healthcare Foundation. Although Phillips acknowledges that they don’t usually speculate about how much a watch will fetch at auction, their hope is that it achieves at least seven-figures.

Rolex Marlon Brando “Apocalypse Now” Rolex GMT-Master

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As the name of the watch suggests, Marlon Brando wore this particular GMT-Master while filming Apocalypse Now. This watch has been steeped in lore — especially after Hodinkee included it in its list of 12 of the Greatest Missing Watches — alongside timepieces from other notables figures like Fidel Castro, Pablo Picasso, and Buzz Aldrin.

In May 2018, Boutros received an email from Petra Fisher — who turned out to be Petra Brando Fisher, Marlon’s daughter — explaining she was in possession of the watch, which was a gift from her father after finishing her undergraduate degree. Encouraged by Phillips’ record-breaking sale of one of Paul Newman’s Daytonas in 2017, she also wanted to sell the watch, albeit for charity.

Rolex Submariner “James Bond 4Liner” Big Crown, Reference 6538

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A watch’s backstory is often what drives up the price. While the two aforementioned examples speak to the power of celebrity, the Rolex Submariner Big Crown in Phillips’ auction is unique for how it was found.

Twenty years ago, a scuba diver found the watch — missing the bracelet and rotating bezel — at the bottom of Lake Erie. For over two decades he never parted with his discovery, but always assumed it was a fake. However, when a friend urged him to reach out to experts, he found out that it was a genuine Rolex with an estimated retail price of between $80,000-$160,000. Let’s see what the auction brings.

Rolex Cosmograph Daytona “Paul Newman Lemon”

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There were many different colors and variations to the Paul Newman-style dials. The Lemon — named for the intense shade of yellow — is one of the rarest and most sought-after versions. But the real key distinguishing feature in this particular model is the white lettering inside the three sub dials which Boutros says makes it especially rare.

“The vast majority of Paul Newman Daytonas with the yellow dial, they call them “champagne” Paul Newman dials, they have gold colored ink inside those sub dials,” Boutros says. “So this distinction is hardly ever seen. It’s extremely rare. This is also fitted in a very rare reference. The rarest of all Daytona References, the Reference 6264. They were produced for just a few short years.”

This particular watch speaks to an era when Rolex was intrigued by experimentation. While the white lettering suggests easier readability for wearers, the product was short lived after the brand introduced screw-down pusher Daytonas.

Rolex Cosmograph Daytona “Paul Newman John Player Special”

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The “John Player Special” references the color scheme featuring a black main dial, gold sub dials, and a black bezel set against the all-gold case and bracelet. To collectors, this scheme resembles the livery used for Lotus race cars in ’70s when John Player Special was a cigarette maker — with those exact colors on their packaging — who sponsored specific cars.

Rolex Seadweller Reference 1665

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There was a time when the Sultan of Oman would order watches directly from Rolex. The resulting products with royal provenance boasted a gold khanjar — the royal symbol of the country. This particular watch is one of the most complete Oman khanjar-watch given to somebody. It comes with its original guarantee, pictures of the gentleman wearing the watch, and a letter explaining how he received it.

“He was an American pilot assigned to help in Oman, Boutros says. “And after a boat accident, he rescued a couple of people. As a gesture of thanks, he received this watch as a gift. And because of this royal provenance and this beautiful gold khanjar on the dial at 6:00, it makes it extraordinary.”

Words by Alec Banks
Features Editor

Alec Banks is a Los Angeles-based long-form writer with over a decade of experience covering fashion, music, sports, and culture.