Kevin O’Leary has revealed that he lost several thousand dollars after betting on Timothée Chalamet to win the Oscar for Best Actor.
O’Leary, known for his role on Shark Tank and his outspoken views on money and risk, shared the story in a recent media appearance following the Academy Awards. He said he was confident Chalamet would take home the award but admitted the bet did not go his way.
Why O’Leary made the bet
O’Leary explained that he believed Chalamet had strong momentum going into Oscars night. The actor had received praise throughout awards season for his performance and was seen by many fans as a serious contender.
Based on that confidence, O’Leary placed a personal bet predicting Chalamet would win. However, the Oscar ultimately went to Michael B. Jordan for his role in Sinners.
O’Leary said the loss was disappointing but not surprising. He compared the situation to investing, noting that even well-researched bets can fail.
Taking the loss in stride
Despite losing money, O’Leary said he was not upset. He described the bet as a calculated risk and said the amount lost was manageable for him. He also joked that betting on awards shows is far less predictable than business investments.
O’Leary added that awards outcomes depend on many factors, including voting trends and industry sentiment. Even strong performances do not guarantee a win.
Chalamet’s Oscars night
Although Chalamet did not win Best Actor, his presence at the ceremony remained a highlight. He received strong support from fans and critics and continues to be seen as one of the leading actors of his generation.
Industry experts say Chalamet is still likely to win an Oscar in the future, given his track record and growing list of high-profile roles.
A reminder about risk
O’Leary’s story quickly gained attention online. Many viewers saw it as a reminder that even experienced investors can make losing bets.
For O’Leary, the loss was part of the game. As he put it, sometimes you win, and sometimes you learn — even on Hollywood’s biggest night.
