LOS ANGELES (Azat TV) – Businessman and television personality Kevin O’Leary made a striking entrance at the 98th Academy Awards on March 15, 2026, blending the worlds of high-stakes finance, sports memorabilia, and Hollywood prestige. O’Leary, who features in the critically acclaimed film Marty Supreme, arrived on the red carpet wearing a custom Tiffany & Co. necklace centered on a rare NBA Triple Logoman card, an asset valued between $25 million and $30 million.
A Red Carpet Display of High-Value Assets
The centerpiece of O’Leary’s ensemble is widely considered one of the most valuable sports collectibles in existence. The custom-made piece features the first-ever PSA 10 graded Triple Logoman card, which contains game-worn jersey patches from basketball legends Michael Jordan, Kobe Bryant, and LeBron James. Surrounded by diamonds and rubies in white gold, the necklace serves as a definitive statement on the growing intersection between extreme-value sports assets and elite fashion. O’Leary’s appearance comes on the heels of a previous red carpet outing at the Screen Actors Guild Awards, where he showcased a signed Jordan and Bryant card estimated at $20 million.
Defending Chalamet Amid Public Backlash
Beyond his display of assets, O’Leary utilized the platform to address the controversy surrounding his Marty Supreme co-star, Timothée Chalamet. The young actor had faced significant public criticism following a February 24 media appearance in which he suggested that interest in ballet and opera was waning. During interviews with media outlets on the red carpet, O’Leary characterized the backlash as a misinterpretation of Chalamet’s broader intent.
“He took a bum rap on that,” O’Leary stated, emphasizing his support for his colleague. “He’s a really great guy. We need these art forms to bring us together.” O’Leary’s defense was accompanied by a personal financial wager; he revealed to reporters that he had bet $1,000 on the prediction market Kalshi that Chalamet would secure the Academy Award for Best Actor. Ultimately, the award went to Michael B. Jordan for his role in Sinners, leaving O’Leary’s specific bet unsuccessful.
Transitioning into Hollywood’s Inner Circle
O’Leary’s presence at the ceremony highlights his deliberate pivot toward acting, a transition he has described as a way to challenge his cognitive comfort zones. Working alongside A-list talent such as Gwyneth Paltrow and Chalamet in Marty Supreme, which garnered nine Oscar nominations, has placed the former venture capitalist at the center of the 2026 awards season conversation. His commitment to the project, which included months of preparation for his red carpet appearance, reflects a broader strategy of leveraging his personal brand within the entertainment industry.
The combination of O’Leary’s unprecedented display of sports-linked wealth and his vocal support for a co-star embroiled in cultural criticism underscores a shift in how high-profile figures use the red carpet not just for fashion, but as a stage for personal brand advocacy and high-stakes signaling.