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
