At most Academy Awards ceremonies, the red carpet is a parade of couture, diamonds and luxury watches. At the Academy Awards, however, investor and television personality Kevin O’Leary brought something different: a piece of sports-collecting history worth roughly $30 million.
The Shark Tank star arrived wearing the famed Exquisite Triple Logoman basketball card as a pendant — a one-of-one collectible that has become one of the most valuable items in the global sports-memorabilia market.
The card’s appeal lies in its rarity and symbolism. Produced by luxury trading-card manufacturer Upper Deck Company, the Exquisite Triple Logoman contains game-worn NBA logo patches from three generations of basketball icons: Michael Jordan, Kobe Bryant and LeBron James. In the collecting world, it’s often described as the sport’s “holy grail.â€
O’Leary’s decision to wear the card — effectively turning it into jewelry for the night — was both spectacle and statement. The investor has been a vocal proponent of trading cards as an alternative asset class, arguing that the market for elite collectibles increasingly mirrors the economics of fine art and luxury watches.
Over the past decade, high-end sports cards have transformed from niche hobby items into institutional-level assets. Auction houses now regularly record eight-figure valuations for the rarest pieces, and funds dedicated to collectibles have emerged alongside traditional investment vehicles.
The Triple Logoman sits at the very top of that pyramid. Because it features three of the most influential figures in modern basketball history, collectors often view it as a singular artifact representing multiple eras of the NBA.
For O’Leary, the Oscars appearance was part marketing stunt, part financial thesis.
Hollywood’s red carpet is built on spectacle. But on this night, the most unusual accessory wasn’t a diamond necklace or vintage couture.
It was a basketball card — and possibly the most valuable one ever made.