Many know Kevin O’Leary from appearing on Shark Tank, as well as Dragon’s Den. Recently, the investor decided to make a flashy statement while making an appearance at the 2026 SAG Awards in Los Angeles. However, it was one pricey accessory that really stole the show.
Kevin O’Leary Flashed An Item Worth Millions While On The Red Carpet
O’Leary is a Canadian businessman and television personality. He is known for co-founding SoftKey Software Products.
On television, O’Leary is known to many for appearing on Shark Tank, the American version of the international Dragon’s Den franchise. In addition, O’Leary also previously appeared on the Canadian edition of the show. He’s also been part of other programs, including Project Earth and The Lang and O’Leary Exchange.
O’Leary recently made an appearance at the 2026 Screen Actors Guild Awards on Sunday. While on the red carpet, he made a statement by flashing one expensive, if unique, item in particular.
During his SAG Awards appearance, O’Leary showed off a $19.2 million Michael Jordan-Kobe Bryant autographed basketball card. He could be seen wearing this pricey accessory around his neck. It was mounted in a diamond-set frame, hanging from a Tiffany chain.
The Shark Tank alum was one of three buyers who purchased the card in August. At the time, the $12.9 million price set a world record for the most ever paid for a sports card. This also made it the second most expensive sports collectible of all time, behind Babe Ruth’s 1932 jersey.
O’Leary Also Shared Just Why He Wanted To Bring The Card To Los Angeles
As noted by The U.S. Express, O’Leary spoke with the Associated Press on the red carpet about the card. At the time, he shared, “I’m looking at this card the same way as if you could have bought a Picasso in 1962.” He also claimed that the card has “done better than crypto.”
O’Leary wasn’t sure how the Tiffany chain and diamond frame impacted the card’s overall value. However, the outlet noted that the chain retails for around $275,000.
The investor also shared just why he wanted to bring the card to the event. According to the outlet, he noted, “I brought this back because I want to bring Kobe back to LA on such a big night in the city. It’s the first time we brought it out; I thought it would be great for the red carpet.” Tragically, Bryant died on January 26, 2020, at the age of 41. He and other occupants, including his daughter, lost their lives during a California helicopter crash in the Calabasas area.
The expensive card was just one part of O’Leary’s ensemble. He also donned a decorated tuxedo jacket and two watches.
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John Witiw has been a writer since at least 2015. He’s covered a variety of topics, especially when it comes to film and television.