‘Shark Tank’s Kevin O’Leary Wears $20 Million Necklace on Actors Awards Red Carpet

It’s not uncommon for entertainers to drizzle themselves in expensive jewelry for the red carpet of a major awards show, but this one was still quite unexpected: Shark Tank‘s Kevin O’Leary, who joined the show’s celebration of his film Marty Supreme, wore over $20 million worth of baubles at Sunday’s (March 1) Actor Awards.

O’Leary, the Shark Tank original who was among the nominees for Outstanding Performance by a Cast in a Motion Picture for his turn as Milton Rockwell in the film, rocked a Kobe Bryant card bejeweled in diamonds and proudly boasted its value on the red carpet.

“We brought Kobe back to L.A. That’s a one of one dual logo, man, signed with Jordan as well. It’s a $20 million card in 2.2 pounds of Tiffany white gold and 100 karats of Tiffany diamonds. I mean, we’re rockin’ it tonight, baby, that’s it,” he told TSN Sports on the red carpet.

O’Leary purchased the card, a 1-of-1 2007-08 Upper Deck Exquisite Collection Dual Logoman Autograph card featuring Kobe Bryant and Michael Jordan, for $12.932 million in August 2025.

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He told Fox Business of the purchase at the time, “The thing that’s amazing about the hobby is the relationship between a father or a mother and a daughter and a son, because if you look at collecting, everything you need to learn about entrepreneurship is baked into what happens when you start to collect cards: ‘Should I buy it? Will it go up in value? Should I sell it?’ These are the decisions that kids that are five and six years old are getting into. And as a result, we got multiple generations, particularly father-sons that have been forever. So, I was really intrigued. And I said, ‘If we go to buy a card, we’re going to buy it. There’s no maybe. We’re gonna buy it.’ And Shyne said, ‘This is the No. 1 card on Earth.’ A lot of it has to do with that gold patch logoman. It’s mesmerizing.”

He also contended that he had no interest in selling the card after acquiring it, saying, “What I do is build indexes. It’s a labor of love – it’s half art, half science. But what’s the emotional connection with the card? For me, with that card, it’s that gold logoman. It’s unique. It’s a piece unique.”

Indeed, it was certainly a unique statement piece when he donned it at the Actor Awards on Sunday night!

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