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The 98th Academy Awards have once again brought together some of the biggest stars in Hollywood under one roof. While everyone has been waiting for the main awards to roll out, an unexpected appearance on the red carpet of the Oscars 2026 stole the limelight. Unlike any actress, it was entrepreneur and TV personality, Kevin O'Leary who turned heads with a stylish entrance. However, the centerpiece of his look was an extravagant piece of jewelry reportedly worth nearly USD 20 million. Here's everything to know about it.
Kevin O'Leary, who is best known for his role as "Mr. Wonderful" on Shark Tank, stole the spotlight at the red carpet of the Oscars 2026. He opted to wear a custom black Dolce & Gabbana tuxedo for the big night. Additionally, Kevin leveled it up with his unique jewelry and two luxury watches, which were previously significant parts of his personal brand.

According to a Newsweek report, the luxury watches included pieces from Rolex and Cartier. They were customised with red accents to match the ruby details on his necklace. However, the centerpiece of the whole look was a remarkable chain with historic basketball memorabilia. It was a custom "Triple Logoman" necklace by Tiffany & Co.

The necklace features an extremely rare trading card with game-used logo patches from three of the greatest basketball players in history,: Michael Jordan, Kobe Bryant, and LeBron James. For those unaware, the card itself is a valuable sports collectible. In fact, some reports claim that it is allegedly the PSA-10 graded Exquisite Triple Logoman card in existence. Meanwhile, the card is encased in the necklace made with 2.2 pounds of white gold, 100 carats of diamonds, and 10 carats of rubies.

Since it is a custom piece, the exact price of the necklace cannot be determined. But Kevin shared that the collectible card alone was traded privately for about USD 26 million. Therefore, the finished piece could be worth around USD 30 million. However, when the actor was asked about the risk of wearing an expensive item on the carpet, he joked that they had heavy security waiting outside the venue.
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Kevin O'Leary did not just stepped on to the red carpet of the Oscars 2026 to showcase his style. Instead, the entrepreneur who made his film debut in the sports drama, Marty Supreme, has received multiple nominations at the ceremony. Kevin plays 'Milton Rockwell', a powerful businessman, in a story set in the 1950s. According to People, when Kevin was asked on the red carpet about the Best Actor award, he placed a USD 1 million bet on a prediction market platform that his co-star, Timothée Chalamet, would win. He even defended him against the recent criticism he received owing to comments about ballet and opera.

The 2026 Oscars ceremony is being held at the Dolby Theatre in Los Angeles. Comedian, Conan O'Brien hosts the ceremony for the second consecutive year. Several things have made headlines this year at the ceremony, from filmmaker, Ryan Coogler's vampire thriller Sinners receiving a record-breaking 16 nominations to One Battle After Another taking home 13 nominations. Moreover, the organisers have also introduced a new competitive category for Best Casting, a first major addition to the Academy Awards since 2001.
What do you think about Kevin O'Leary's 20 million custom NBA "Triple Logoman" necklace at Oscars 2026?
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