Kevin O'Leary Says He Wants To Be Buried With His Watch Collection When He Dies — 'All Of These Watches Are Coming Into My Coffin. I'm Like The Pharaoh Of Time'

Kevin O’Leary, also known as Mr. Wonderful on "Shark Tank," is not only a famed investor but also a passionate watch collector.

In a November 2023 interview with GQ, O’Leary shared his deep attachment to his watch collection and his unique approach to collecting. Unlike many collectors who view watches as assets, O’Leary considers his collection too sacred to be treated as such. He told GQ, “All of these watches are coming into my coffin. I'm like the pharaoh of time.”

During the Grand Seiko’s U.S. collector meetup at the Roosevelt Hotel in Hollywood, O’Leary was seen in his signature style — a black Prada suit, red pocket square and a watch on each wrist. He participated in a panel discussion alongside other watch-world figures, praising Grand Seiko’s Zaratsu polishing and their “insane” dials.

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O’Leary’s approach to collecting is unique. He chases rare pieces, and brands know that to get his attention, they need to offer bands in his trademark red. He collects various brands like Rolex, Patek Philippe, Audemars Piguet and Grand Seikos. He keeps his watches in different safes around the world after experiencing thefts of his collection twice.

In his conversation with GQ, O’Leary shared insights on the current state of watch collecting. He observed a trend of men wanting to experiment with different colors and more fashion-forward designs. He also noted Grand Seiko’s manufacturing advantage in embracing color and creating unique dial textures.

O’Leary’s journey into watch collecting began in Geneva, where he bought his first Omega Speedmaster Moonwatch in 1975, a piece he still treasures. His collection includes a wide range of watches, from high-end to entry-level, showcasing his broad appreciation for the art of watchmaking.

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Unlike Microsoft Corp. Co-Founder Bill Gates, who is known for wearing a $25 Casio watch, O’Leary stands at the other end of the spectrum as an avid collector of luxury watches. O’Leary’s collection, worth hundreds of thousands of dollars according to Celebs Watch Spotter, showcases his deep passion for horology. Among his prized possessions are several iconic and valuable timepieces.

One notable watch in O’Leary’s collection is the Patek Philippe 5711 series, launched in 2006 to mark the 30th anniversary of the Nautilus. Known for its steel construction and octagon-shaped bezel with a black-blue dial, the 5711’s value has skyrocketed since its discontinuation in 2022. Originally priced at $30,620, it now commands over $100,000 in the market.

O’Leary also owns two Rolex Daytona 116500 watches, a model first introduced in 1963 and named after the Daytona race. This iconic watch has seen various improvements over the years. O’Leary personalized one of his Daytonas by replacing its ceramic bezel with a red strap, aligning with his preference for red accents. While the Daytona retails for $14,550, it can sell for upward of $36,000 on the secondary market. In 2019, O’Leary auctioned one of his Daytona watches for $56,700, with the proceeds supporting charitable causes.

Another eye-catching timepiece in O’Leary’s collection is the Rolex Daytona Reference Number 116588TBR, also known as the Eye of the Tiger. This watch features a diamond-studded bezel and a dial with a tiger-stripe pattern adorned with diamonds. O’Leary’s version is customized with his signature red strap, and it can be priced at more than $200,000 on the secondary market.

O’Leary also cherishes the F.P. Journe Élégante 48 mm Titalyt, a watch from a brand celebrated for its in-house movement designs and multiple Aiguille d'Or grand prizes. His Élégante 48 mm Titalyt, featuring a titanium case and luminescent sapphire dial, has a market price exceeding $60,000, despite its retail price being less than $14,000.

Despite his extensive collection, O’Leary maintains a level of secrecy about the exact number of watches he owns, a precaution taken after thefts. His collection is so securely stored that, as he puts it, “It's impossible to steal my watches again because you'd have to travel to nine cities and break into nine different bank vaults.”

The interview highlights O’Leary’s deep passion for watches, not just as investments but as cherished possessions, reflecting his personality and approach to life and business.

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