Uncategorized
Kevin O’Leary Lost $1,000 Betting on Timothée Chalamet to Win Best Actor at the 2026 Oscars
Mar
Kevin O’Leary, the well-known investor and star of the TV show Shark Tank, recently revealed that he lost $1,000 after betting that Timothée Chalamet would win Best Actor at the Academy Awards. The surprising admission came during a red-carpet interview on Oscars night, highlighting O’Leary’s confidence in his Marty Supreme co-star.
Despite his optimism, the award ultimately went to Michael B. Jordan for his performance in Sinners, leaving O’Leary’s wager unsuccessful.
Kevin O’Leary’s $1,000 Bet on Timothée Chalamet
While speaking on the red carpet, Kevin O’Leary shared that he placed a $1,000 bet on prediction platform Kalshi, confident that Chalamet would take home the Oscar for Best Actor in a Leading Role.
“He’s a really great guy,” O’Leary said during the interview. “I just put 1,000 bucks on Kalshi walking in here that he’s going to win.”
Unfortunately for the investor-turned-actor, the bet didn’t pay off. If Chalamet had won the award, O’Leary would have received around $3,000 in payout.Despite his optimism, the award ultimately went to Michael B. Jordan for his performance in Sinners, leaving O’Leary’s wager unsuccessful.
Michael B. Jordan Wins Best Actor at the 2026 Oscars
At the start of the ceremony, odds showed Michael B. Jordan as the favorite, with approximately 58% probability of winning the category. Meanwhile, Timothée Chalamet held the second-highest odds at 33%.
Other nominees in the category included:
- Wagner Moura for The Secret Agent
- Leonardo DiCaprio for One Battle After Another
- Ethan Hawke for Blue Moon
Jordan ultimately secured the win for his performance in Sinners, beating a strong lineup of acclaimed actors.
O’Leary Defends Chalamet After Opera and Ballet Controversy
Leading up to the awards ceremony, Chalamet had faced criticism for comments about the declining popularity of opera and ballet. However, O’Leary dismissed concerns that the controversy would impact the actor’s Oscar chances.
According to O’Leary, the backlash was unfair.
“The kid is a great kid,” he said. “He took a bum rap on that. And by the way, it gave a lot of promo to opera houses and ballet.”
The businessman remained supportive of his co-star despite the controversy.
Kevin O’Leary’s Acting Role in Marty Supreme
Interestingly, O’Leary wasn’t just attending the Oscars as a celebrity guest. He actually appeared in the sports drama Marty Supreme, starring alongside Chalamet and Gwyneth Paltrow.
In the film, O’Leary plays Milton Rockwell, a villainous businessman in the story centered around competitive table tennis.
O’Leary explained that joining the film was an opportunity to step outside his comfort zone.
“You should get out of your comfort zone as often as you can because you exercise the most important muscle in your body — your brain,” he said.
Even his agent initially advised against it, warning him that he had no acting experience.
But O’Leary decided to try anyway.
Will Kevin O’Leary Continue Acting?
After enjoying the experience on Marty Supreme, O’Leary hinted that he may continue exploring acting opportunities.
“Now I’m going to try and do one a year,” he said.
His experience working with A-list talent like Chalamet and Paltrow left a strong impression.
He also praised Chalamet’s acting method, describing how the actor would fully immerse himself in character before scenes.
“He would just walk around a light stand and come back in character,” O’Leary recalled. “Boom, sparks flying off his fingertips.”
Marty Supreme Earns Nine Oscar Nominations
Although Chalamet didn’t win Best Actor, Marty Supreme still had a major presence at the 2026 Oscars, earning nine nominations, including:
- Best Picture
- Best Actor
- Best Director
- Best Original Screenplay
- Best Casting
- Best Cinematography
- Best Film Editing
- Best Production Design
- Best Costume Design
The film’s impressive nomination list highlights its impact during this year’s awards season.
