Sylvester Stallone Sells His Knockout Watch Collection, Including the Most Valuable Modern Timepiece Sold in Sotheby’s History
By ERIC GROSSMAN
Sat, Jun 8, 2024 7:00am
3 min
3 min
Sylvester Stallone’s legacy as one of the most notable watch collectors of the 21st century was cemented in New York this week, as 11 of the actor’s timepieces sold for US$6.7 million—beating its presale estimate—at Sotheby’s.
The highlight of the sale was the Academy Award winner’s Patek Philippe Grandmaster Chime, which sold for US$5.4 million (surpassing its pre-sale estimate of US$2.5 million to US$5 million), a result that set a pair of benchmarks for the auctioneer. It’s the third-most valuable wristwatch sold in Sotheby’s history, and marks a record for a modern watch sold by Sotheby’s, topping the US$4.5 million sale of a Richard Mille Reference RM53-02 last October.
“The sale of the Patek Philippe Grandmaster Chime was an unrepeatable celebration, not only of a masterpiece by the most revered Swiss-watchmakers of technical excellence, but also of the legendary icon that is Sylvester Stallone, who has been a deeply influential and admired collector for many decades,” Geoff Hess, Sotheby’s head of watches, Americas, said in a statement.
Sotheby’s
On Wednesday, more than 100 attendees filled Sotheby’s saleroom, and once the Grandmaster Chime (Reference 6300G-010) hit the block, a four-minute bidding war ensued among five bidders, according to the auction house. In the end, the watch was sold to a private collector from Asia. ( Stallone paid US$2.2 million for the watch in 2021. )
“To feel the pulse of collectors racing with excitement in pursuit of absolute top-caliber material was tremendous, and an homage to the art of collecting at the highest level,” Hess said.
Considered to be a holy grail among followers of haute horology, the Grandmaster Chime was the result of a project initiated by Philippe Stern in 2007 to create the most intricate wristwatch in the brand’s history. The development, production, and assembly spanned 100,000 hours, according to Sotheby’s.
Stallone’s Grandmaster Chime was the first example of the model to appear at auction, aside from one specifically created for, and sold at, a Christie’s charity auction in November 2019 for CHF 31 million (US$35 million) . It remains the highest price for a watch ever sold at auction.
Hess himself went home with one of Stallone’s watches, as the winner of a five-minute bidding battle for the actor’s olive green Patek Philippe Nautilus. The 2021 stainless steel watch featuring an olive-green dial and diamond-set bezel sold for US$492,000, exceeding its pre-sale estimate of US$400,000.
Sotheby’s
Stallone’s collection, assembled over the course of more than 20 years, also included timepieces from Rolex, Audemars Piguet, and Piaget, as well as unique and screen-worn watches from Panerai.
Other highlights included the actor’s Audemars Piguet Royal Oak Tourbillon (Reference 26730OR.OO.1320OR.01)—a gorgeous piece created for the 50th anniversary of the Swiss watchmaker’s Royal Oak collection in 2022. It sold for US$228,000, exceeding its pre-sale high estimate of US$200,000; and a Panerai Luminor Submersible (Reference PAM00382) worn by Stallone in the 2012 film The Expendables 2 that sold to an online buyer for US$96,000, blowing past its pre-sale estimate of US$30,000 to US$60,000.
“I enjoy the collecting process like so many others in this passionate community, who don’t just see watches as an accessory, but admire them for their history, craftsmanship, artistry—but most importantly—how they make them feel,” Stallone said in a statement when the sale was announced. “Looking at these watches, I feel truly lucky to have owned them; they serve as a reminder that hard work pays off.”
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Selloff in bitcoin and other digital tokens hits crypto-treasury companies.
By GREGORY ZUCKERMAN AND VICKY GE HUANG
Mon, Nov 10, 2025 3 min
3 min
The hottest crypto trade has turned cold. Some investors are saying “told you so,” while others are doubling down.
It was the move to make for much of the year: Sell shares or borrow money, then plough the cash into bitcoin, ether and other cryptocurrencies. Investors bid up shares of these “crypto-treasury” companies, seeing them as a way to turbocharge wagers on the volatile crypto market.
Michael Saylor pioneered the move in 2020 when he transformed a tiny software company, then called MicroStrategy , into a bitcoin whale now known as Strategy. But with bitcoin and ether prices now tumbling, so are shares in Strategy and its copycats. Strategy was worth around $128 billion at its peak in July; it is now worth about $70 billion.
The selloff is hitting big-name investors, including Peter Thiel, the famed venture capitalist who has backed multiple crypto-treasury companies, as well as individuals who followed evangelists into these stocks.
Saylor, for his part, has remained characteristically bullish, taking to social media to declare that bitcoin is on sale. Sceptics have been anticipating the pullback, given that crypto treasuries often trade at a premium to the underlying value of the tokens they hold.
“The whole concept makes no sense to me. You are just paying $2 for a one-dollar bill,” said Brent Donnelly, president of Spectra Markets. “Eventually those premiums will compress.”
When they first appeared, crypto-treasury companies also gave institutional investors who previously couldn’t easily access crypto a way to invest. Crypto exchange-traded funds that became available over the past two years now offer the same solution.
BitMine Immersion Technologies , a big ether-treasury company backed by Thiel and run by veteran Wall Street strategist Tom Lee , is down more than 30% over the past month.
ETHZilla , which transformed itself from a biotech company to an ether treasury and counts Thiel as an investor, is down 23% in a month.
Crypto prices rallied for much of the year, driven by the crypto-friendly Trump administration. The frenzy around crypto treasuries further boosted token prices. But the bullish run abruptly ended on Oct. 10, when President Trump’s surprise tariff announcement against China triggered a selloff.
A record-long government shutdown and uncertainty surrounding Federal Reserve monetary policy also have weighed on prices.
Bitcoin prices have fallen 15% in the past month. Strategy is off 26% over that same period, while Matthew Tuttle’s related ETF—MSTU—which aims for a return that is twice that of Strategy, has fallen 50%.
“Digital asset treasury companies are basically leveraged crypto assets, so when crypto falls, they will fall more,” Tuttle said. “Bitcoin has shown that it’s not going anywhere and that you get rewarded for buying the dips.”
At least one big-name investor is adjusting his portfolio after the tumble of these shares. Jim Chanos , who closed his hedge funds in 2023 but still trades his own money and advises clients, had been shorting Strategy and buying bitcoin, arguing that it made little sense for investors to pay up for Saylor’s company when they can buy bitcoin on their own. On Friday, he told clients it was time to unwind that trade.
Crypto-treasury stocks remain overpriced, he said in an interview on Sunday, partly because their shares retain a higher value than the crypto these companies hold, but the levels are no longer exorbitant. “The thesis has largely played out,” he wrote to clients.
Many of the companies that raised cash to buy cryptocurrencies are unlikely to face short-term crises as long as their crypto holdings retain value. Some have raised so much money that they are still sitting on a lot of cash they can use to buy crypto at lower prices or even acquire rivals.
But companies facing losses will find it challenging to sell new shares to buy more cryptocurrencies, analysts say, potentially putting pressure on crypto prices while raising questions about the business models of these companies.
“A lot of them are stuck,” said Matt Cole, the chief executive officer of Strive, a bitcoin-treasury company. Strive raised money earlier this year to buy bitcoin at an average price more than 10% above its current level.
Strive’s shares have tumbled 28% in the past month. He said Strive is well-positioned to “ride out the volatility” because it recently raised money with preferred shares instead of debt.
Cole Grinde, a 29-year-old investor in Seattle, purchased about $100,000 worth of BitMine at about $45 a share when it started stockpiling ether earlier this year. He has lost about $10,000 on the investment so far.
Nonetheless, Grinde, a beverage-industry salesman, says he’s increasing his stake. He sells BitMine options to help offset losses. He attributes his conviction in the company to the growing popularity of the Ethereum blockchain—the network that issues the ether token—and Lee’s influence.
“I think his network and his pizzazz have helped the stock skyrocket since he took over,” he said of Lee, who spent 15 years at JPMorgan Chase, is a managing partner at Fundstrat Global Advisors and a frequent business-television commentator.
