Kevin O’Leary turned heads on the red carpet at the 98th Academy Awards by wearing a 2004 Upper Deck Exquisite All NBA Access Pass — the rare “Triple Logoman.” The one-of-one, PSA 10–graded card features game-used NBA logo patches from Michael Jordan, LeBron James and Kobe Bryant.
O’Leary had the slab set into a custom Tiffany & Co. case fashioned from 2.2 pounds of white gold and studded with diamonds and rubies, then mounted on a chain. He matched the piece with a bespoke Dolce & Gabbana jacket he said took seven months and several artisans to produce.
The Jordan/James/Bryant Triple Logoman has never been offered at auction; it was purchased privately in 2019 by O’Leary’s business partner Matt Allen, with assistance from Ken Goldin of Goldin Auctions.
This wasn’t O’Leary’s first time showcasing a seven-figure sports card. At the Actor Awards in March he wore a 2007–08 Upper Deck Exquisite Dual Logoman Autographs card (Michael Jordan and Kobe Bryant) encased by Tiffany & Co. in a holder set with 101.32 carats of diamonds, 10 carats of rubies and white gold. O’Leary, Allen and entrepreneur Paul Warshaw paid $12.9 million for that card at Heritage Auctions last August, a record price for a sports card.
O’Leary attended the Oscars after appearing as Milton Rockwell, a wealthy businessman married to Gwyneth Paltrow’s Kay Stone, in the film Marty Supreme. The movie earned nine Academy Award nominations, including best picture, director, actor, original screenplay, casting, cinematography, production design, editing and costume design.
