Kevin O’Leary Loses $1,000 Bet on Timothée Chalamet at the 2026 Oscars

Entrepreneur and television personality Kevin O’Leary wagered $1,000 on his Marty Supreme costar, Timothée Chalamet, to win Best Actor at the 98th Academy Awards, but lost the bet as Michael B. Jordan took home the trophy.

O’Leary’s Confidence in Chalamet

Speaking on the red carpet before the ceremony, O’Leary revealed he placed the bet through the prediction market platform Kalshi, stating, “I just put 1,000 bucks on Kalshi walking in here that he’s going to win.”^[1] He expressed his belief in Chalamet’s talent, describing him as “a really great guy.” ^[2]

The Outcome and Odds

Michael B. Jordan won the Best Actor award for his performance in Sinners. ^[2] Chalamet was nominated for his role in Marty Supreme, where O’Leary played the villainous Milton Rockwell. Other nominees in the category included Wagner Moura, Leonardo DiCaprio, and Ethan Hawke. ^[2]

Prior to the ceremony, Jordan was considered the frontrunner, with a 58 percent chance of winning on Kalshi, while Chalamet had 33 percent odds. ^[2] Had Chalamet won, O’Leary’s $1,000 bet would have yielded approximately $3,000.

Defending Chalamet Amid Controversy

Despite the loss, O’Leary defended Chalamet against recent criticism regarding his comments about opera and ballet. He stated, “I understand the voting stops long before that controversy happened,” adding, “The kid is a great kid. He took a bum rap on that.” ^[1] He also suggested that Chalamet’s comments inadvertently promoted interest in the performing arts, saying, “By the way, he gave a lot of promo to opera houses and ballet.”^[4]

O’Leary’s Experience with Marty Supreme

O’Leary shared his enthusiasm for joining the cast of Marty Supreme, stating, “I always sense you should get out of your comfort zone as often as you can, because you exercise the most key muscle in your body, your brain.” ^[3] He praised his costars, including Chalamet and Gwyneth Paltrow, and noted that even his agent discouraged him from taking the role. ^[3] He also indicated a desire to continue acting, aiming to grab on one role per year.

Marty Supreme received nine nominations at the 2026 Oscars, including Best Picture, Best Actor, and Best Director. ^[2]