TLDR
Contents
- The Shark Tank celebrity investor placed a $1,000 wager on Kalshi predicting Timothée Chalamet would claim best actor at the Oscars
- O’Leary appears as tycoon Milton Rockwell in “Marty Supreme,” sharing the screen with Chalamet
- Despite being the early favorite, Chalamet’s Oscar chances diminished following backlash over remarks about ballet and opera
- The best actor award ultimately went to Michael B. Jordan for his role in “Sinners”
- O’Leary argued the controversy couldn’t have affected results since voting concluded beforehand, though the outcome proved unfavorable regardless
When Kevin O’Leary arrived at the Oscars red carpet, he wasn’t just there for the glamour and ceremony. The business mogul and “Shark Tank” personality had actual financial skin in the game regarding the best actor category’s outcome.
Speaking with Variety, O’Leary revealed he’d placed a four-figure bet through Kalshi, a prediction market platform. His wager? That Timothée Chalamet, his co-star from “Marty Supreme,” would walk away with the coveted best actor statue.
In “Marty Supreme,” O’Leary portrays Milton Rockwell, a wealthy tycoon character, appearing alongside Chalamet who carries the film’s leading role.
For weeks leading up to the ceremony, Chalamet was viewed as the clear favorite to win. However, the race’s dynamics shifted dramatically in the final stretch.
Backlash and Changing Fortunes
The turning point came earlier in the month when Chalamet made polarizing statements during a public appearance. He expressed disinterest in working within ballet or opera, dismissing these disciplines as art forms operating under a mentality of preserving traditions “even though no one cares about this anymore.”
The artistic community responded with sharp criticism. Speculation mounted about whether the backlash might influence Academy members’ voting decisions.
On the red carpet, O’Leary pushed back against this narrative. He emphasized that the Academy’s voting window had closed well before the controversial statements made headlines.
“I know the voting stopped long before that controversy happened,” O’Leary told Variety.
His observation was technically accurate. The timeline supported his position. However, when results were announced, the outcome didn’t favor his prediction.
Michael B. Jordan’s campaign had been building steam throughout awards season. His portrayal in “Sinners” earned him the Screen Actors Guild Award for best actor prior to the Oscars ceremony.
The SAG victory proved significant. Since SAG members represent a substantial portion of the Academy’s voting body, that win signaled a major momentum shift in the race.
Jordan Secures the Victory
When presenters revealed the winner at the ceremony, Jordan’s name emerged from the envelope. The “Sinners” star claimed the best actor Oscar, bringing Chalamet’s lengthy reign as presumptive winner to an end.
The result left O’Leary down $1,000 from his Kalshi prediction market position. His wager didn’t deliver returns.
Kalshi operates as a federally regulated prediction market where participants can place bets on various real-world outcomes. The platform has experienced substantial growth recently, especially surrounding political elections and entertainment industry honors.
O’Leary has established himself as a regular Kalshi user and has publicly advocated for the prediction market sector on multiple occasions.
While the monetary loss was negligible for someone with O’Leary’s estimated net worth running into hundreds of millions of dollars, it certainly added an interesting dimension to his Oscar night experience.
The ballet and opera controversy ultimately couldn’t be blamed for the lost wager. Voting had concluded before the incident generated publicity.
Jordan’s triumph represented the culmination of a powerful awards season performance. His earlier SAG Award win had already indicated the competition was more competitive than initial projections suggested.
Chalamet still earned recognition through his nomination for “Marty Supreme.” The production received acknowledgment across multiple Oscar categories during the broadcast.
O’Leary participated in the ceremony both as an attendee and as part of the film’s ensemble. He engaged with numerous media representatives while making his way down the red carpet ahead of the show.
Kalshi has issued no public statement regarding the total betting volume on this year’s best actor category.
