When Kevin O'Leary stepped onto the red carpet at the 98th Academy Awards on March 15, 2026, he wasn't just making a fashion statement—he was making history. The businessman, television personality, and “Shark Tank” investor stunned onlookers with a custom necklace featuring one of the rarest and most valuable sports collectibles ever assembled: the legendary Triple Logoman card. This eye-popping accessory, estimated to be worth between $25 million and $30 million, instantly became the talk of the Oscars, blending the glitz of Hollywood with the fervor of high-stakes sports memorabilia collecting.
O’Leary, who also appeared at the ceremony as an actor in the critically acclaimed film "Marty Supreme," arrived in a look that had been months in the making. His black Dolce & Gabbana jacket, embroidered with meticulous attention to detail, reportedly took seven months to complete, stitched by multiple artisans. But as dazzling as the jacket was, it was the necklace—a bespoke creation by Tiffany & Co.—that truly stole the show. According to coverage from multiple outlets, the necklace was crafted from 2.2 pounds of white gold, embedded with diamonds and carefully matched rubies, all designed to frame and showcase the card at its heart.
The centerpiece, the 2004 Upper Deck Exquisite All NBA Access Pass Triple Logoman, is a 1-of-1 numbered, PSA 10-graded card. It features authentic NBA logo patches cut from game-worn jerseys of three of basketball’s greatest legends: Michael Jordan, Kobe Bryant, and LeBron James. The card has never been to public auction, adding to its mystique and value. As reported by sources including ESPN and The Hollywood Reporter, the card was acquired in a private deal in 2019 by O'Leary's business partner, Matt Allen, with the assistance of Goldin Auctions' Ken Goldin. The card’s singular status and pristine condition—being the only PSA 10 graded Exquisite Logoman card known to exist—have cemented its place as a holy grail among collectors.
In the hours leading up to the event, O’Leary teased his bold look with a “get ready with me” video on Instagram, giving fans a behind-the-scenes glimpse at the final fitting. "Doing a final fitting ahead of the Oscars," he wrote, his excitement palpable. The anticipation among both fashion and sports memorabilia enthusiasts was high, and O’Leary did not disappoint.
This wasn’t the first time O’Leary has paired high fashion with high-value collectibles. Earlier in March 2026, he made headlines at the Screen Actors Guild Awards by wearing another showstopping piece: a signed 2007-08 Upper Deck Exquisite Collection Dual Logoman Autographs card featuring Michael Jordan and Kobe Bryant. That card, too, was encased by Tiffany & Co., this time in a holder featuring 101.32 carats of diamonds, 10 carats of rubies, and white gold. O’Leary, Allen, and entrepreneur Paul Warshaw had purchased the Dual Logoman card at Heritage Auctions in August 2025 for a staggering $12.9 million—a record price for a sports card at the time.
But the Triple Logoman necklace at the Oscars represented a new level of extravagance, even for O’Leary. The card’s value—between $25 million and $30 million, according to estimates—makes it one of the most expensive items ever worn on a red carpet, rivaling even the most storied pieces of jewelry in Hollywood history. The fusion of luxury jewelry design and the world of elite sports collectibles created a buzz that rippled far beyond the Dolby Theatre, sparking conversations from Wall Street to basketball courts around the globe.
O’Leary’s appearance at the Oscars wasn’t just about personal style or record-breaking bling. He was also there as a cast member of "Marty Supreme," a film that had garnered nine Academy Award nominations, including best picture, director, actor, original screenplay, casting, cinematography, production design, editing, and costume design. O’Leary played Milton Rockwell, a wealthy businessman married to Gwyneth Paltrow’s character, Kay Stone. The film’s critical acclaim and the star power of its ensemble cast made it one of the evening’s most anticipated contenders, and O’Leary’s dual role as both actor and headline-making fashion icon added another layer of intrigue to the night.
The Triple Logoman card itself is the stuff of legend in the sports memorabilia world. Produced in 2004 by Upper Deck as part of the Exquisite Collection, the card features pieces of the iconic NBA logo patches from jerseys worn by Jordan, Bryant, and James during actual games. The fact that it is the only one of its kind—numbered 1-of-1—and has achieved a perfect PSA 10 grade means it sits in a category all its own. According to information shared by O’Leary and his associates, the card has never been offered at public auction, and its provenance is well-documented, adding to its allure for collectors and investors alike.
For O’Leary, the fusion of sports history, luxury craftsmanship, and personal branding seems to be a winning formula. His willingness to wear such valuable items in public—on the world’s most-watched red carpets, no less—has brought new attention to the world of sports collectibles, a market that has seen explosive growth and record prices in recent years. The fact that these cards are now being treated as wearable art, rather than simply locked away in vaults, is a testament to their cultural significance and enduring appeal.
Not everyone, of course, is convinced that such displays are purely about passion for the game or the art of collecting. Some critics have raised eyebrows at the spectacle, questioning whether the blending of high finance, celebrity culture, and sports memorabilia risks turning cherished artifacts into mere status symbols. Others, however, see O’Leary’s boldness as a celebration of both sports history and artistic innovation—a way to bring the stories of legendary athletes into new and unexpected arenas.
Whatever the perspective, there’s no denying the impact of O’Leary’s Oscars appearance. With the Triple Logoman necklace, he managed to bridge the worlds of business, entertainment, fashion, and sports in a single, unforgettable moment. As the cameras flashed and the world watched, the message was clear: sometimes, the most valuable things aren’t just worn—they’re lived, shared, and celebrated in the spotlight.
In a year when both Hollywood and the sports memorabilia market are reaching new heights, O’Leary’s statement piece serves as a reminder that history, artistry, and ambition can come together in the most unexpected—and dazzling—ways.