Shark Tank investor Kevin O'Leary made a splash at the 98th Academy Awards by wearing a diamond-encrusted Triple Logoman card featuring Michael Jordan, Kobe Bryant, and LeBron James. The 1-of-1 PSA 10-graded card, encased in a bespoke Tiffany & Co. holder with 2.2 pounds of white gold, diamonds, and rubies, turned heads on the red carpet.

This wasn't O'Leary's first seven-figure sports card fashion statement. He previously wore a 2007-08 Upper Deck Exquisite Collection Dual Logoman Autographs card of Jordan and Bryant, encased with 101.32 carats of diamonds and 10 carats of rubies. The trio of O'Leary, Matt Allen, and Paul Warshaw paid $12.9 million for that card at Heritage Auctions last August, setting a record for sports card purchases.

The Triple Logoman card, produced in 2004, has never been auctioned. Allen acquired it in 2019 through Goldin Auctions' Ken Goldin in a private purchase. O'Leary attended the Oscars after playing Milton Rockwell in Marty Supreme, which received nine Academy Award nominations including Best Picture and Best Director.