Marty Supreme star Kevin O’Leary sports $30 million sporting memorabilia at Oscars ceremony
While the 98th Academy Awards celebrated cinematic achievement, one attendee made a statement that blurred the lines between red carpet fashion and high-stakes asset management. Kevin O’Leary, the investor and reality television personality turned actor, arrived not just as a nominee but as a walking vault, sporting a piece of sports memorabilia reportedly valued at up to $30 million around his neck.
The centrepiece of O’Leary’s outfit was a one-of-a-kind 2004 Upper Deck Exquisite Collection “Triple Logoman” trading card, encased in a bespoke Tiffany & Co. setting of white gold, diamonds, and rubies. The card itself is the pinnacle of basketball collecting, featuring game-worn NBA logo patches from three legends: Michael Jordan, Kobe Bryant, and LeBron James. According to ESPN, it is the only PSA 10 graded Exquisite Logoman card known to exist, a perfect rating from the professional authentication service that sends its value stratospheric.
The $30 Million Necklace: A Private Market Icon
In an interview with CNN on the Oscars red carpet, O’Leary claimed the card was last traded privately for $26 million and estimated its current worth at around $30 million. Its journey to his neck was a private affair; the card was acquired in 2019 by his business partner, Matt Allen (also known as “Shyne”), in a transaction facilitated by Goldin Auctions and has never been to public auction.
This appearance continues O’Leary’s pattern of treating ultra-rare sports cards as both investment and accessory. Just weeks earlier, at the Actor Awards on March 1, 2026, he wore another record-setting piece: a 2007-08 Upper Deck Exquisite Collection Dual Logoman Autographs card featuring Jordan and Bryant. That card was purchased in August 2025 by O’Leary, Allen, and a third investor, Paul Warshaw, for $12.9 million at public auction, setting a new record price and surpassing the $12.6 million paid for a 1952 Topps Mickey Mantle card in 2022.
For O’Leary, these are not mere collectibles but a serious asset class. He has been quoted comparing them to holdings in Bitcoin and gold, arguing that such rare items “defy recessions” and offer “extraordinary capital gains.”
From ‘Shark Tank’ to Josh Safdie’s Vision
O’Leary attended the Oscars as part of the ensemble for the nominated film *Marty Supreme*, a 2025 sports comedy-drama directed by Josh Safdie. In the film, which stars Timothée Chalamet as 1950s table tennis player Marty Mauser, O’Leary plays Milton Rockwell, a ruthless businessman.
His casting was deliberate. Director Josh Safdie reportedly sought an actor who embodied a “real asshole” and found O’Leary’s public “Mr. Wonderful” persona a perfect fit. O’Leary has acknowledged having no prior acting experience and essentially played a version of himself, even rewriting scenes to make his character more ruthless. Despite this, his performance has garnered positive reviews.
The film itself, A24’s most expensive production at the time with a budget of $60–70 million, received four Academy Award nominations, including Best Picture and Best Director. However, it was a competitor, *Sinners*, that provided the night’s upset for O’Leary in a personal wager.
A Lost Bet on a Co-Star
Confident in his colleague’s chances, O’Leary revealed to CNN that he had placed a $1,000 bet on the prediction market platform Kalshi for Timothée Chalamet to win the Best Actor award. He reasoned that Oscar voting closes early, insulating the result from any recent controversies Chalamet was involved in. “The kid is a great kid. He took a bum rap on that,” O’Leary stated.
His confidence was misplaced. The Best Actor trophy was awarded to Michael B. Jordan for his role in *Sinners*, leaving O’Leary out of pocket on his bet. The loss, however, was likely a minor footnote for someone who had just paraded a potential $30 million asset on one of the world’s most watched stages, cementing his unique position at the intersection of finance, film, and the frenzied world of collectibles.
