Kevin O’Leary Says His $20M Basketball Card Investment ‘Defies Recessions’

The Shark Tank investor wore it around his neck at the Actor Awards on March 1.

BY AVA LEVINSON, NEWS WRITER

(Photo by Christopher Polk/2026GG/Penske Media via Getty Images)

Kevin O’Leary, who played Milton Rockwell in Marty Supreme, showed up to the 2026 Actor Awards in Los Angeles yesterday wearing something that has people talking, and this time it wasn’t rainbow pants covered in butterflies or a red cheetah-print button down. Instead, it was a basketball card hanging from a diamond necklace… worth $19.2 million. 

The card features basketball legends Michael Jordan and Kobe Bryant along with their autographs. O’Leary purchased it for $13 million, helping it break the record for the most-expensive trading card to be sold at an auction. It surpassed the 1952 Topps Mickey Mantle #311, which sold for $12.6 million in 2022.

The chain is made up of 101 carats of Tiffany & Co. diamonds and another 10 carats of rubies set in white gold, according to O’Leary’s Instagram post. 

“The weight of this thing is over two pounds of solid gold and diamonds,” said O’Leary. 

How Canva Became the Power Player in the AI Design Wars

The famed Shark Tank investor told Page Six that it was the first time he had brought the accessory out.

“I brought this back because I want to bring Kobe back to LA on such a big night in the city,” he said. 

The Card Was a Major Investment

O’Leary bought the card with two other investors at an auction in August 2025 for almost $13 million. He told CNBC that such cards are “so rare that the prices continue to appreciate, and they seem to defy recessions.”

© Inc.com