Marty Supreme star Kevin O’Leary may have lost a $1,000 bet at the Oscars but, if his attire on Sunday night told us anything, it’s that he wouldn’t have cared one bit.
The 71-year-old actor, who appears as Milton Rockwell in Josh Safdie’s 2025 film, rocked up to the glitzy event in California wearing an embroidered black Dolce & Gabbana jacket which reportedly took seven months to complete.
However, it wasn’t the sleek jacket which caught attention online as, instead, fans were left stunned by an iconic piece of sports memorabilia – worth up to $30 million – which he transformed into a chain for the centerpiece of his outfit on the night.
In a bespoke Tiffany and Co. case – embedded with diamonds, rubies and ‘2.2 pounds of white gold’ – O’Leary flexed a one-of-one Triple Logoman NBA card.
The rare collectible features game-worn patches from a trio of NBA legends; Michael Jordan, Kobe Bryant and LeBron James.
The card holds elevated prestige within the collectible community due to the fact it’s the only PSA 10 graded Exquisite Logoman card known in existence.
Kevin O’Leary turned heads at the Oscars with a piece of sports memorabilia worth $30 million
In a bespoke Tiffany and Co. case – embedded with diamonds, rubies and ‘2.2 pounds of white gold’ – O’Leary flexed a 1-of-1 Triple Logoman NBA card
According to ESPN, the Jordan/James/Bryant card – released as part of the 2004 Upper Deck Exquisite Collection – has never been to auction.
However, O’Leary’s business partner, Matt Allen, reportedly acquired it in 2019 during a private purchase.
Speaking to CNN on the night, O’Leary said: ‘This is the most famous basketball card in history. It was made 22 years ago. It has all three stars and their logoman.
‘It’s one-of-one. Last time it traded privately was $26 million. So it’s probably worth somewhere around $30 million now.’
NBA Logoman cards are premier, ultra-rare collectibles featuring the official NBA logo patch taken directly from game-worn jerseys, often paired with autographs.
O’Leary’s lavish Oscars outing marks the most recent occasion that the actor has made a splash in the sports memorabilia world.
Back in August 2025, a trio of investors – including O’Leary – set the record for the richest card ever sold at public auction.
The trio spent $12,932,000 on a rare, one-of-one patch trading card featuring NBA icons Michael Jordan and Kobe Bryant.
O’Leary said: ‘It’s one-of-one. Last time it traded privately was $26 million. So it’s probably worth somewhere around $30 million now.’
In August 2025, O’Leary was part of a trio of investors who bought a rare card for $12.9 million
That price surpassed the previous record, held for the 1952 Topps Mickey Mantle #311 card which sold for $12.6 million.
The new record holder is a highly coveted card from the 2007-08 Upper Deck Exquisite Collection.
This card earns its value by being the only card ever produced to have both Bryant and Jordan’s autographs, while also featuring dual NBA Logoman patches from each athlete’s game-worn jerseys.
Meanwhile, O’Leary also made headlines at the Oscars when he lost a $1,000 bet after the lead star walked away without the Best Actor trophy on Sunday night.
The 71-year-old was certain Timothee Chalamet – who played Marty Mauser – was going to scoop the top prize for the role.
Speaking to CNN on the red carpet at the bash, Kevin said: ‘He’s a really great guy…
‘I just put 1000 bucks on Kalshi walking in here that he’s going to win, because I know the voting stops long before that controversy happened.
‘The kid is a great kid. He took a bum rap on that. And by the way, gave a lot of promo to opera houses and ballet.’
