Oscars always bring a lot of fun and an unexpected element. This year was no different, as a surprise moment came when Timothee Chalamet didn’t win the Best Actor award at the Oscars 2026, which ended up costing Kevin O’Leary a $1,000 bet and a surprising loss. The “Shark Tank” star revealed that he was so convinced of Chalamet’s victory that he wagered money on him through a prediction market platform, predicting he would win. However, the “Dune” actor lost to Michael B. Jordan in the “Best Actor” category, making O’Leary lose the bet.
Kevin O’Leary bet $1000 on Timothee Chalamet ahead of Oscars 2026
Timothee Chalamet losing the “Best Actor” award at the 2026 Oscars apparently didn’t affect only him but also his “Marty Supreme” co-star, Kevin O’Leary, who lost $1000. At the ceremony, O’Leary said he had placed a bet on Chalamet. He said that he predicted Chalamet would win the “Best Actor” award for his role in “Marty Supreme.”
He revealed that he put a $1,000 bet on Kalshi, a prediction platform. The video was shared on X (formerly Twitter) by @Variety. When the hosts asked O’Leary about Chalamet’s recent controversial statement and what he is like in real life, he responded that he is a “great guy.”
The Shark Tank star said, “He’s a really great guy. His mother’s really nice. That whole thing about the opera — by the way, I just put $1,000 on Kalshi walking in here.”
He added, “He’s going to win, because I know the voting stopped long before that controversy happened.” This was in reference to a recent statement by Chalamet, in which he reportedly said that nobody really “cares” about ballet and opera anymore. The controversial statement received a lot of backlash, with many celebrities criticizing him for dismissing traditional art forms.
However, O’Leary said that Chalamet is a great guy in real life. He shared, “That kid is great kid. He took a bum rap on that. By the way, he gave a lot of promo to opera houses and ballet.”
While he thought the “Wonka” actor would win, he lost when the award for “Best Actor” went to Michael B. Jordan for the film “Sinners.”
Originally reported by Chhavi Puri on RealityTea.
