Rocky star Sylvester Stallone will sell 11 timepieces at Sotheby’s on June 5, including an ultra-rare Patek Philippe Grandmaster Chime watch that originally sold for around $2.5 million. 

This will be the first time a Grandmaster Chime has been put up for commercial auction. At the Only Watch charitable auction in 2019, a steel model sold for $31 million, setting a record.

Stallone’s version of the two-sided timepiece, with its 20 complications—the most Patek has ever put in a wristwatch—is in white gold. It has five different chiming modes, features a perpetual calendar and can track two time zones. The watch is so rare, even for the vaunted Swiss watchmaker, that it comes with an elaborate presentation box that includes a collection book and plaque, both with Stallone’s name, an original certificate, cuff links and an iPad in a Patek Philippe leather case.  The watch itself remains in its plastic wrapping; the action star has never worn it.

Sotheby’s has assigned Stallone’s Grandmaster Chime an estimate of $2.5 million to $5 million, though it could certainly go for more. 

That watch joins other sought-after Patek Philippes, as well as watches from Audemars Piguet, Cartier, Rolex and Piaget. A group of Panerai watches, including the one Stallone wore in the film Expendables 2, round out the collection, which will sell as part of the Sotheby’s Important Watches sale in New York City.

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Stallone, now 77, says he’s owned the watch long enough and it’s time to move on. He is a longtime watch collector who at one point owned around 100 timepieces. “I’ve been a client and enthusiast of Patek Philippe for many years,” he tells Bloomberg. “When I look back on my time with Patek and the watches I’ve collected, I feel a sense of pride. There’s this feeling that I’ve made it. ”

According to Stallone, he bought the Grandmaster Chime as a collector with no intention to wear it. He says the watch was not easy to come by; he had to appeal to the highest levels at the company to be allocated one. He likens the timepiece to a Monet—a work of art—and says letting it go is “bittersweet.”

“When you have a great watch and it grows in popularity,” he says, “it’s a constant reminder that hard work pays off.”

Two highly coveted Nautilus models are in the sale, too. A 2021 stainless steel reference 5711/13000A-001, with a green sunburst dial and diamonds on the bezel, is estimated to sell for $200,000 to $400,000 for its extreme rarity. A steel blue-dial reference 5711/1A-001 is estimated to sell in a range of $50,000 to $100,000. The 5711 line has been discontinued, causing its values on the secondary market to soar.

Stallone also has a longstanding relationship with Panerai, the maker of thick dive watches that is owned by Swiss luxury juggernaut Richemont. After the actor wore one in the 1994 film Daylight, the company experienced a boost in public interest. “But for Sylvester Stallone, Panerai wouldn’t be what it it is today,” says Geoff Hess, Sotheby’s head of watches for the Americas. “I’m not sure we’d even know about Panerai.” 

Stallone’s friend Arnold Schwarzenegger then began wearing Panerai, and Stallone went on to wear a Panerai Bronzo in the film Expendables 2; he can be seen wearing it in the poster. According to Hess, he gave Bronzos to key fellow cast members including Jason Statham, Dolph Lundgren, Liam Hemsworth, Chuck Norris and Schwarzenegger.

“I always thought the bronze PAM00382 Luminor was incredible, because of the metal,” Stallone says. “Its design reminds me of the Titanic—a porthole—and has this industrial feel. I knew I had to wear it in the movie, because it was going to make such a statement.”

The one he’s selling is numbered 000, “so it’s likely the first one Panerai ever made,” he adds. “I put this thing through its paces—underwater, above water, in the sand, fight scenes—you name it. It was my companion throughout that film and longer than that. I’ve derived so much pleasure from this watch. And now, why not have someone else enjoy it as much as I did?”

Other watches in the group include an Audemars Piguet Royal Oak Tourbillon 50th Anniversary that’s estimated in the range of $100,000 to $200,000 and a pink gold Rolex Day-Date for $25,000 to $50,000.

Sotheby’s Hess managed to land the sale because of a yearslong relationship with Stallone. When Hess was at rival auction house Phillips, he worked with the actor in 2020 on a sale of five watches, including that Daylight Panerai. He also says a distant tie stretches all the way back to Hess’s childhood. 

“If you look at the credits at the end of every Rocky movie, they say: ‘This film is dedicated to the enduring memory of Jane Oliver,’” Hess says. Oliver was Stallone’s first manager in the late 1970s—and Hess’s cousin. “She gave me an autographed picture that says ‘To Geoffrey from Sly,’ he says. ”I’ve had it for 47 years.” 

Hess connected with Stallone in 2019, and they began working together. He knew Stallone had the Grandmaster Chime, and together they worked out the right time to sell it. “I’m gearing up for what I hope could be a record for a modern watch” at a non-charity auction, Hess says. “We’re certainly shooting for a record for a watch from the 21st century.”