Kevin O’Leary made a significant impact at the 2026 Academy Awards by wearing a remarkable Triple Logoman card on the red carpet. This unique card features game-used NBA logo patches from basketball legends Michael Jordan, LeBron James, and Kobe Bryant, showcasing O’Leary’s penchant for high-value sports memorabilia.
The card, a 2004 Upper Deck Exquisite All NBA Access Pass, is a one-of-a-kind item, graded PSA 10. It was encased in a bespoke Tiffany & Co. case, which weighs 2.2 pounds and is embedded with 101.32 carats of diamonds and 10 carats of rubies, further emphasizing its extravagant nature.
O’Leary’s fashion choice is not new; he has previously worn seven-figure sports cards as fashion statements. This time, he complemented the card with a custom-made Dolce & Gabbana jacket that took seven months to create, highlighting his commitment to style.
In addition to his fashion statement, O’Leary placed a $1,000 bet on Timothée Chalamet to win the Oscar for Best Actor. Unfortunately for O’Leary, Chalamet lost the award to Michael B. Jordan, who had a 58 percent chance of winning according to pre-award predictions.
The film Marty Supreme, in which O’Leary portrayed Milton Rockwell, received nine nominations at the Oscars, showcasing the film’s critical acclaim. Despite the loss for Chalamet, O’Leary’s involvement in the film and his betting strategy drew attention.
O’Leary’s business partner acquired the Triple Logoman card in 2019 with assistance from Goldin Auctions, and last August, O’Leary and his partners paid $12.9 million for a different sports card at Heritage Auctions, further illustrating the lucrative nature of sports memorabilia.
Reflecting on his experiences, O’Leary stated, “I always feel you should get out of your comfort zone as often as you can, because you exercise the most important muscle in your body, your brain.” This philosophy seems to guide his bold choices both in fashion and in his betting strategies.
As the awards season progresses, O’Leary’s unique blend of fashion and sports betting continues to capture public interest. Details remain unconfirmed regarding future bets or fashion choices, but O’Leary’s presence at the Oscars has certainly set a high bar for future appearances.
