Kevin O'Leary says he lost $1,000 bet on Timothée Chalamet at Oscars

Kevin O’Leary said he lost a $1,000 bet after backing Timothée Chalamet to win the Academy Award for Best Actor at the 2026 Oscars.

The Shark Tank investor shared the detail while speaking on the red carpet during the ceremony. O’Leary appeared alongside Chalamet in the film Marty Supreme and said he had placed the wager on the prediction market platform Kalshi shortly before the event.

“He's a really great guy,” O’Leary said in an interview with Variety. “I just put 1,000 bucks on Kalshi walking in here that he's going to win.”

Chalamet was nominated for Best Actor for his role in Marty Supreme. However, the award went to Michael B. Jordan for his performance in Sinners.

Other nominees in the category included Wagner Moura for The Secret Agent, Leonardo DiCaprio for One Battle After Another and Ethan Hawke for Blue Moon.

O’Leary also addressed criticism that Chalamet received earlier in awards season following comments about the declining popularity of opera and ballet. He said he did not believe the controversy would influence the result.

“I know the voting stops long before that controversy happened,” he said. “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.”

Chalamet starred in Marty Supreme, a table tennis drama. The film received multiple nominations at the 2026 Academy Awards, including Best Picture, Best Actor, Best Director, Best Writing for Original Screenplay, Best Casting, Best Cinematography, Best Film Editing, Best Production Design and Best Costume Design.

Despite receiving nine nominations, Marty Supreme did not win in any category at the ceremony.

Chalamet’s performance in the film had been widely discussed during the awards season, contributing to the film’s presence across several major categories at the Academy Awards.