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Kevin O’Leary refused to apologize for defending Timothée Chalamet at the 2026 Oscars. The Shark Tank star also revealed he lost his $1,000 bet wagering on the actor to win Best Actor just hours after Chalamet faced backlash for controversial comments about ballet and opera.
🔥 Quick Facts
- Oscar Bet Placed: O’Leary wagered $1,000 on Kalshi that Chalamet would win Best Actor
- Standing Firm: O’Leary called the backlash unfair, saying Chalamet “took a bum rap”
- Marty Supreme: The film earned 9 Oscar nominations including Best Picture endorsement from O’Leary
- March 15, 2026: O’Leary defended his costar during red carpet interviews hours before voting ended
O’Leary Doubles Down on Chalamet Defense at Historic Oscar Night
At the 2026 Academy Awards, Kevin O’Leary made his position crystal clear on the red carpet. Speaking to Variety and CNN, the Shark Tank host vigorously defended his Marty Supreme costar against mounting criticism. O’Leary stated that Chalamet took a bum rap regarding his controversial ballet and opera remarks. The venture capitalist emphasized that voting had concluded long before the mini-controversy erupted.
O’Leary refused to back down when discussing Chalamet’s character. He praised the young actor as a “really great guy” and highlighted his professionalism on set. The 71-year-old businessman remained resolute in his support, noting that the incident had actually benefited classical arts by generating heightened conversation.
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The Controversial Opera Comments That Sparked Backlash
Earlier in March 2026, Chalamet ignited controversy during a public discussion. The actor stated that he didn’t want to work in ballet or opera “where nobody cares anymore.” His words immediately triggered backlash across social media and entertainment circles. Critics accused him of being dismissive toward classical performing arts and their dedicated audiences.
The controversy gained momentum just days before the Oscars ceremony. However, O’Leary argued that voting had already concluded before the backlash surfaced. Notably, award show host Conan O’Brien and other celebrities referenced the comments during the ceremony. Despite this, O’Leary maintained that Chalamet deserved support and understanding.
Oscar Predictions and Financial Stakes
| Event Detail | Information |
| Bet Amount | $1,000 on Kalshi platform |
| Category | Best Actor in a Leading Role |
| Predicted Winner | Timothée Chalamet |
| Actual Winner | Michael B. Jordan (Sinners) |
O’Leary expressed confidence on the red carpet before the ceremony began. He placed his $1,000 wager believing Chalamet would prevail. The businessman reasoned that voting behavior wouldn’t be influenced by comments made after ballots closed. Ultimately, Michael B. Jordan captured the Best Actor prize, leaving O’Leary and other Chalamet supporters disappointed.
“He’s a really great guy. I just put 1000 bucks on Kalshi walking in here that he’s going to win, because I know the voting stops long before that controversy happened. The kid is a great kid. He took a bum rap on that.”
— Kevin O’Leary, Shark Tank Host and Marty Supreme Costar
Inside the Marty Supreme Film and Oscar Nominations
Marty Supreme emerged as one of the night’s most celebrated films with nine total Oscar nominations. The sports drama earned recognition in major categories including Best Picture, Best Director, and Best Original Screenplay. Chalamet received his nomination forBest Actor, showcasing his range in the leading role as protagonist Marty Mauser.
O’Leary plays the antagonistic Milton Rockwell in the film, adding gravitas to the production. During interviews, he enthusiastically discussed his acting debut and commitment to the project. O’Leary revealed that he worked alongside A-listers like Gwyneth Paltrow, describing the experience as enriching and rewarding despite initial doubts from his agent.
Will Kevin O’Leary Apologize for His Vocal Support of Chalamet?
Despite the controversy and his lost wager, O’Leary showed no signs of backing down from his position. The Shark Tank judge maintained that Chalamet didn’t deserve the intense criticism leveled at him. O’Leary emphasized that industries benefit from passionate public discourse, even when comments miss the mark. He suggested that Chalamet’s remarks inadvertently sparked renewed interest in classical performing arts.
O’Leary refused to issue any apology, standing firmly beside his costar through the controversy. The businessman’s commitment to defending young talent reflects his broader philosophy about mentorship and support within competitive industries. Whether audiences will forgive Chalamet’s comments remains uncertain, but at least one influential figure in entertainment isn’t wavering in his backing.
Sources
- Variety – Kevin O’Leary defends Timothée Chalamet at 2026 Oscars red carpet interview
- Business Insider – Coverage of O’Leary’s $1,000 Kalshi bet on Chalamet for Best Actor
- USA Today – 2026 Oscars coverage with Chalamet ballet and opera controversy details
