Kevin O’Leary made a remarkable entrance at the 32nd Annual Screen Actors Guild Awards, held on March 1, captivating attendees and onlookers alike with an extraordinary display of luxury and sports history. The well-known investor and television personality stunned the crowd on the red carpet by wearing a necklace valued at an astonishing $20 million. This was no ordinary piece of jewelry; it was a dazzling tribute to two basketball legends, Kobe Bryant and Michael Jordan.
The centerpiece of O’Leary’s striking accessory is a rare and unique 2007–08 Upper Deck Exquisite Collection Dual Logoman Autograph card, which features autographs from both Bryant and Jordan. This collectible is famously one-of-a-kind, a fact that O’Leary proudly emphasized during his red carpet interview. He explained that the card was purchased in August 2025 for nearly $13 million and has since been transformed into an opulent necklace, crafted with 2.2 pounds of Tiffany white gold and embellished with an impressive 100 carats of Tiffany diamonds. The result is an unparalleled fusion of sports memorabilia and high-end jewelry design.
O’Leary’s enthusiasm for the piece was evident as he described it as a “one of one dual logo” signed by two of the greatest NBA icons. He expressed a sentimental connection to the necklace, saying, “We brought Kobe back to L.A.… We’re rockin’ it tonight,” highlighting the emotional significance behind the collectible. His passion for sports card collecting goes beyond mere investment; he has often spoken about how the hobby instills valuable decision-making skills from a young age and helps forge meaningful bonds across generations.
Importantly, O’Leary made it clear that he has no intention of parting with this extraordinary item. He referred to it as a “piece unique,” underscoring its irreplaceable value not only in monetary terms but also in its cultural and personal importance. This stance reflects his long-standing appreciation for rare collectibles as both financial assets and treasured keepsakes.
Aside from his dazzling necklace, Kevin O’Leary was also recognized for his acting work at the ceremony. He was nominated for Outstanding Performance by a Cast in a Motion Picture for his role as Milton Rockwell in the film Marty Supreme. While the awards season typically showcases glamorous fashion and sparkling diamonds, O’Leary’s diamond-encrusted sports card necklace stood out as one of the most unconventional and talked-about accessories of the night, blending the worlds of entertainment, sports, and luxury in a truly unique way.
