Kevin O'Leary's Bold Bet on Timothée Chalamet at Oscars 2026 Falls Short
Kevin O'Leary's Oscars Bet
Oscars 2026: Entrepreneur and TV personality Kevin O'Leary recently disclosed that he placed a significant wager on his co-star Timothée Chalamet to secure the Best Actor award at the 98th Academy Awards. During a red carpet interview prior to the event, the Shark Tank investor revealed he had bet on Chalamet using a prediction market platform. "He's an incredible guy," O'Leary stated. "I just put $1,000 on Kalshi as I walked in here, believing he would win." Unfortunately for O'Leary, his bet did not yield results, as the Best Actor award went to Michael B. Jordan for his remarkable role in Ryan Coogler’s Sinners. Chalamet was nominated for his performance in Marty Supreme, where O'Leary also appeared as the antagonist Milton Rockwell. Other nominees included Wagner Moura for The Secret Agent, Leonardo DiCaprio for One Battle After Another, and Ethan Hawke for Blue Moon.
Prior to the ceremony, Jordan was seen as the leading candidate for the award, boasting a 58 percent chance of winning on the Kalshi platform, while Chalamet had a 33 percent likelihood. Had Chalamet emerged victorious, O'Leary's $1,000 wager could have returned nearly $3,000. Despite the disappointing outcome, O'Leary stood by Chalamet amidst recent backlash regarding the actor's remarks on the waning popularity of opera and ballet. "I know the voting concluded long before that controversy arose," he commented. "The kid is fantastic. He received undue criticism for that. Plus, he promoted opera houses and ballet significantly."
However, the most significant disappointment of the evening was Marty Supreme itself, which failed to secure any wins out of its nine nominations at the 98th Academy Awards, despite being a strong contender. The film, directed by Josh Safide, lost in major categories such as Best Picture, Best Director, Best Actor, and Best Original Screenplay, along with nominations for Cinematography, Film Editing, and Production Design.
Earlier, O'Leary had shared insights about his acting experience in Marty Supreme, a sports drama focused on competitive table tennis featuring a star-studded cast, including Gwyneth Paltrow alongside Chalamet. He acknowledged that transitioning into acting was challenging and not everyone supported his choice. "I believe in stepping out of your comfort zone as often as possible, as it exercises the most vital muscle in your body, your brain," he expressed. "I truly enjoyed it. Collaborating with A-listers like Gwyneth and Timmy was amazing. Even my agent advised against it, saying, 'You don't know how to act.' I replied, 'Why not give it a shot?'"
The other notable winners of the night included One Battle After Another and Frankenstein.