Shark Tank Star Kevin O'Leary Loses $1,000 Bet on Timothée Chalamet's Oscar Victory
The 2026 Academy Awards delivered one of the night's most significant upsets when Timothée Chalamet failed to secure the Best Actor trophy for his role in Marty Supreme. The disappointment extended beyond the actor himself to his co-star, entrepreneur and Shark Tank personality Kevin O'Leary, who placed a last-minute $1,000 wager on Chalamet's success.
Hollywood's Biggest Night Sees Major Surprise
The film industry gathered on Sunday, 15 March, for the prestigious Oscars ceremony, where Ryan Coogler's Sinners and Paul Thomas Anderson's One Battle After Another emerged as the evening's big winners. However, the Best Actor category provided a dramatic twist, with Michael B. Jordan claiming the award for his performance in Sinners, defeating the heavily favoured Chalamet.
Kevin O'Leary, making his acting debut in Marty Supreme as Milton Rockwell, the husband of Gwyneth Paltrow's character Kay Stone, was so convinced of Chalamet's impending victory that he bet $1,000, equivalent to approximately £752, on the outcome. Speaking to Variety on the red carpet before the ceremony, the 71-year-old O'Leary praised Chalamet as "a really great guy" and revealed, "I just put 1000 bucks on [sports betting site] Kalshi walking in here that he's going to win."
Controversy and Campaign Challenges
Timothée Chalamet had been considered the frontrunner for Best Actor for much of the awards season, thanks to his portrayal of ambitious table tennis champion Marty Mauser in Josh Safdie's chaotic film Marty Supreme. However, his campaign faced a significant setback in recent weeks following controversial remarks he made about opera and ballet.
During a discussion with Matthew McConaughey at a CNN and Variety town hall, Chalamet commented on audiences' shortened attention spans, stating, "I don’t want to be working in ballet or opera, where it’s like, 'Hey! Keep this thing alive, even though no one cares about this anymore.'" The comments sparked backlash from cultural figures, including ballet legend Misty Copeland and film director Steven Spielberg.
Despite the controversy, Kevin O'Leary remained steadfast in his support, insisting that the remarks would not affect Chalamet's Oscar chances. He argued, "I know the voting stops long before that controversy happened. The kid is a great kid. He took a bum rap on that. And by the way, gave a lot of promo to opera houses and ballet."
Oscars Night Reactions and Aftermath
The opera and ballet controversy was humorously addressed by host Conan O'Brien during his opening monologue, where he joked about tight security due to concerns over attacks from both communities. Chalamet was seen laughing at the joke alongside his girlfriend, Kylie Jenner.
Ultimately, the bookmakers' odds proved accurate, with Michael B. Jordan overtaking Chalamet in the final weeks before the ceremony. While O'Leary's $1,000 bet did not pay off, the incident highlights the unpredictable nature of awards season and the passionate support that actors can garner from their colleagues. The loss marks a memorable footnote in an Oscars night filled with surprises and celebrated achievements across the film industry.
