ESPN staffMar 15, 2026, 07:30 PM ET
"Shark Tank" investor Kevin O'Leary made waves for wearing the 2004 Upper Deck Exquisite All NBA Access Pass, affectionately known as a Triple Logoman, at the 98th Academy Awards red carpet on Sunday. It features game-used NBA logo patches worn by Michael Jordan, LeBron James and Kobe Bryant.
O'Leary had the 1-of-1 numbered, PSA 10-graded card slab from the first year Triple Logoman cards were produced inserted into a bespoke Tiffany & Co. case with "2.2 pounds of white gold" embedded with diamonds and rubies and affixed to a chain. O'Leary also wore a custom-made Dolce & Gabbana jacket that, by his own admission, took seven months to make, stitched by multiple people.
The Jordan/James/Bryant Triple Logoman from the 2004 Upper Deck Exquisite Collection has never been to auction, but one of O'Leary's business partners, Matt Allen, acquired it in 2019 with the help of Goldin Auctions' Ken Goldin in a private purchase.
Sunday didn't mark the first time O'Leary has donned a seven-plus-figure sports card as a fashion statement.
In early March's Actor Awards, O'Leary had the 2007-08 Upper Deck Exquisite Collection Dual Logoman Autographs Michael Jordan & Kobe Bryant card encased by Tiffany & Co. into a holder featuring 101.32 carats of diamonds and 10 carats of rubies and white gold. O'Leary, Allen and entrepreneur Paul Warshaw paid $12.9 million for the card at Heritage Auctions last August -- a record paid for a sports card.
O'Leary attended the Oscars after playing Milton Rockwell, a wealthy businessman married to Gwyneth Paltrow's Kay Stone, in "Marty Supreme."
"Marty Supreme" was nominated for nine Academy Awards, including best picture, director, actor, original screenplay, casting, cinematography, production design, editing and costume design.
