Kevin O’Leary, the star of “Marty Supreme,” might have lost a $1,000 wager at the Oscars, but judging by his outfit on Sunday night, it seemed he was unfazed by the loss.

The 71-year-old actor, set to appear as Milton Rockwell in Josh Safdie’s upcoming 2025 film, made a striking entrance at the glamorous event in California. He donned an intricately embroidered black jacket by Dolce & Gabbana, a piece that reportedly took seven months to complete.

However, the standout feature of his ensemble wasn’t the elegant jacket. Instead, fans were captivated by a legendary piece of sports memorabilia, valued at up to $30 million, which O’Leary ingeniously fashioned into a chain as the focal point of his attire.

Encased in a custom-designed Tiffany & Co. case, adorned with diamonds, rubies, and crafted from 2.2 pounds of white gold, O’Leary showcased a unique Triple Logoman NBA card.

This rare collectible includes game-worn patches from three NBA icons: Michael Jordan, Kobe Bryant, and LeBron James.

The card is held in high esteem among collectors, as it is the only PSA 10 graded Exquisite Logoman card known to exist.

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.’