Kevin O’Leary, renowned entrepreneur and longtime investor on the hit show Shark Tank, added an unexpected flair to the 32nd Annual Screen Actors Guild Awards with a truly eye-catching accessory. On March 1, as he arrived on the red carpet, O’Leary stunned attendees and photographers alike by sporting an extraordinary necklace valued at approximately $20 million. This bold fashion statement quickly became one of the most talked-about highlights of the evening.
The centerpiece of O’Leary’s necklace is a rare and highly coveted 2007–08 Upper Deck Exquisite Collection Dual Logoman Autograph card, which features signatures from two of basketball’s greatest icons: Kobe Bryant and Michael Jordan. This one-of-a-kind collectible is not just a card but a symbol of sports history and immense value. O’Leary originally acquired the card in August 2025 for a staggering $12.932 million, underscoring its rarity and significance in the sports memorabilia world.
What makes this piece even more remarkable is its transformation into a lavish jewelry item. The card has been meticulously set into a necklace crafted from 2.2 pounds of Tiffany white gold, further embellished with an impressive 100 carats of Tiffany diamonds. This fusion of sports memorabilia and high-end jewelry created a truly unique and extravagant accessory that captured the attention of everyone present at the ceremony.
During his red carpet interview, O’Leary expressed immense pride in owning such a distinctive item. He described the card as a “one of one dual logo” autograph, highlighting its exclusivity as the only known card signed by both NBA legends. With a touch of nostalgia and reverence, he remarked, “We brought Kobe back to L.A. … We’re rockin’ it tonight,” emphasizing the emotional connection and significance the card holds for him personally.
O’Leary has often spoken about the deeper value of collecting sports cards, beyond mere financial investment. He believes the hobby imparts important life skills, such as decision-making and strategic thinking, from a young age. Moreover, he has highlighted how collecting can strengthen bonds across generations, creating shared experiences and memories within families. Despite the card’s astronomical price tag, O’Leary has made it clear that he has no intention of parting with this prized possession, referring to it as a “piece unique” that transcends monetary worth.
Aside from his striking jewelry, O’Leary was also present at the awards as a nominee for Outstanding Performance by a Cast in a Motion Picture, recognized for his role as Milton Rockwell in the film Marty Supreme. While the awards season is typically known for glamorous gowns and sparkling diamonds, O’Leary’s diamond-encrusted sports card necklace stood out as one of the most unconventional and memorable accessories of the night, blending the worlds of sports, business, and entertainment in a spectacular fashion.
