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 Oscars 2026 apparently didn’t only affect him but also his “Marty Supreme” co-star Kevin O’Leary, making him suffer a loss of $1000. At the ceremony, O’Leary shared that he 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 the recent controversial statement made by Chalamet 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 made by Chalamet, where 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 suffered a loss as the award in the “Best Actor” category went to Michael B. Jordan for the film, “Sinners.”
