In a surprising turn of events at the 2026 Academy Awards, entrepreneur and Shark Tank personality Kevin O'Leary suffered a financial loss after betting $1,000 on his Marty Supreme co-star Timothée Chalamet to win the Best Actor award. The wager, placed on the sports betting site Kalshi, ultimately proved unsuccessful as Chalamet lost out to Michael B. Jordan, who took home the prestigious Oscar for his performance in Ryan Coogler's film Sinners.
O'Leary's Confident Bet on Chalamet
Speaking to Variety on the red carpet before the ceremony, the 71-year-old O'Leary expressed unwavering confidence in Chalamet's chances, despite bookmakers' odds favoring Jordan in the weeks leading up to the event. "I just put 1000 bucks on Kalshi walking in here that he's going to win," O'Leary declared, adding that Chalamet was "a really great guy." This marked a significant personal investment from O'Leary, who made his acting debut in Josh Safdie's chaotic film Marty Supreme, playing Milton Rockwell opposite Gwyneth Paltrow's character Kay Stone.
The Controversy That Shook the Campaign
Chalamet's Oscar campaign faced unexpected turbulence in recent weeks following controversial remarks he made about opera and ballet. During a CNN and Variety town hall discussion with Matthew McConaughey about declining audience attention spans, Chalamet offhandedly commented, "I don't want to be working in ballet or opera, where it's like, 'Hey! Keep this thing alive, even though no one cares about this anymore.'"
These statements triggered substantial backlash from cultural figures, including ballet legend Misty Copeland and acclaimed film director Steven Spielberg. The controversy became a talking point during the Oscars ceremony itself, with host Conan O'Brien joking in his opening monologue about heightened security due to concerns about "attacks from both the opera and ballet communities." Chalamet was seen laughing at the joke alongside his girlfriend Kylie Jenner.
O'Leary's Defense of His Co-Star
Despite the widespread criticism, O'Leary remained steadfast in his support of Chalamet, insisting that the controversy would not affect the Oscar outcome. "I know the voting stops long before that controversy happened," O'Leary explained. "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 had been considered the frontrunner for Best Actor earlier in the awards season for his portrayal of ambitious table tennis champion Marty Mauser in Marty Supreme. However, his campaign was perceived to have declined significantly in the final weeks before the Oscars, with Jordan ultimately securing the victory.
Hollywood's Biggest Night Delivers Surprises
The film industry gathered on Sunday, March 15, 2026, for Hollywood's most celebrated evening, where Sinners and Paul Thomas Anderson's One Battle After Another emerged as the major winners of the night. While Chalamet's loss represented one of the ceremony's most notable upsets, it also resulted in a tangible financial consequence for his supportive co-star Kevin O'Leary, who learned that even confident bets can sometimes fall short in the unpredictable world of awards season.
