TLDR
- The “Shark Tank” investor placed a $1,000 wager on Kalshi backing Timothée Chalamet to win the best actor Oscar
- O’Leary and Chalamet appear together in “Marty Supreme,” where the businessman plays Milton Rockwell
- The “Dune” star entered awards season as the favorite but faced setbacks following divisive remarks about classical arts
- The best actor trophy ultimately went to Michael B. Jordan for his role in “Sinners”
- Despite pointing out that Academy members voted before the controversy erupted, O’Leary’s bet still failed
When Kevin O’Leary arrived at the Oscars red carpet, he wasn’t just there to support his film. The celebrity investor from “Shark Tank” had skin in the game—literally.
Speaking with Variety, O’Leary revealed he’d put $1,000 on the line through Kalshi, a prediction market platform. His bet? That Timothée Chalamet, his fellow cast member from “Marty Supreme,” would win the best actor award.
In “Marty Supreme,” O’Leary portrays Milton Rockwell, a wealthy businessman, appearing opposite Chalamet, who carries the film as its star.
For most of the awards season, Chalamet appeared destined to win. However, the final weeks saw a dramatic shift in the race’s dynamics.
Backlash and Changing Fortunes
Chalamet found himself in hot water earlier in the month following remarks he made at a public appearance. During the event, he criticized ballet and opera, describing them as art forms clinging to relevance despite diminishing public interest.
The statements sparked outrage across the arts world. Observers began speculating whether the fallout might influence Academy voters against him.
When asked about this on the red carpet, O’Leary brushed off the notion. He emphasized that Academy members had already submitted their ballots well before the controversy erupted.
“I know the voting stopped long before that controversy happened,” O’Leary told Variety.
His logic seemed sound. The chronology supported his position. Unfortunately for O’Leary, the final results didn’t align with his prediction.
Michael B. Jordan had been steadily building momentum throughout the season. His work in “Sinners” earned him the SAG Award for best actor, a ceremony that preceded the Oscars.
That SAG triumph proved pivotal. Since actors comprise the voting body for those awards, and many of them also hold Academy membership, the win signaled a potential upset brewing.
The Envelope Reveals Jordan’s Victory
When presenters announced the winner during the ceremony, Jordan’s name emerged. He captured the best actor Oscar for “Sinners,” derailing Chalamet’s expected coronation.
The result left O’Leary out $1,000. His prediction market gamble on Kalshi came up empty.
Kalshi operates as a federally regulated platform allowing users to place bets on various real-world outcomes. The service has experienced significant growth recently, especially surrounding political contests and entertainment honors.
O’Leary has publicly championed the platform and the broader prediction market sector. He’s been among its more prominent advocates.
Given O’Leary’s estimated net worth in the nine-figure range, the financial sting was minimal. Nevertheless, the wager added an interesting dimension to his Oscars attendance.
The businessman couldn’t attribute his loss to the ballet and opera scandal. As he correctly noted, ballots had been cast before that firestorm ignited.
Jordan’s victory represented the culmination of a strong finish to awards season. His SAG win had already indicated the race was far more competitive than early prognosticators anticipated.
Despite the loss, Chalamet earned recognition through his nomination for “Marty Supreme.” The production received acknowledgment across multiple Oscar categories.
O’Leary attended the festivities wearing dual hats—as both an audience member and a performer in one of the year’s notable films. He made the rounds on the red carpet, discussing the evening with various media organizations.
Kalshi has remained silent regarding the total betting activity on this year’s best actor race.
