TLDR
- Shark Tank’s Kevin O’Leary placed a $1,000 wager on Kalshi backing Timothée Chalamet to win the best actor Oscar
- The investor appears alongside Chalamet in “Marty Supreme,” portraying tycoon Milton Rockwell
- Despite being the early favorite, Chalamet’s chances diminished following backlash over remarks about ballet and opera
- The best actor Oscar ultimately went to Michael B. Jordan for his role in “Sinners”
- O’Leary pointed out that Academy voting had concluded before Chalamet’s controversy emerged
Kevin O’Leary arrived at the Oscars ceremony with more at stake than just celebrating his film. The celebrity investor had real money on the line in the best actor competition.
Speaking with Variety on the red carpet, O’Leary revealed he’d staked $1,000 through Kalshi, the prediction market platform. His bet? That Timothée Chalamet, his co-star from “Marty Supreme,” would walk away with the best actor trophy.
The pair collaborated on “Marty Supreme,” with O’Leary taking on the role of Milton Rockwell, a business magnate. Chalamet carries the film as its leading man.
For most of awards season, Chalamet was viewed as the clear favorite to win. However, the final weeks saw a dramatic shift in momentum.
Backlash and Changing Fortunes
Chalamet found himself embroiled in controversy earlier in the month following statements he made at a public appearance. He expressed disinterest in working within ballet or opera, describing them as artistic fields with an attitude of preserving traditions “even though no one cares about this anymore.”
The comments sparked significant criticism from arts advocates and industry professionals. Questions arose about whether the backlash might influence Academy voters.
On the red carpet, O’Leary brushed aside such concerns. He emphasized that Academy members had already submitted their ballots before the controversy gained traction.
“I know the voting stopped long before that controversy happened,” O’Leary told Variety.
His observation was accurate regarding the timeline. The voting window had indeed closed. However, the final results suggested other factors were at play.
Michael B. Jordan had been building momentum throughout the season. His compelling work in “Sinners” secured him the SAG Award for best actor, a ceremony that preceded the Oscars.
That SAG victory proved significant. Since actors comprise the voting body for both awards, the win signaled a potential upset brewing.
Jordan Claims the Prize
When presenters announced the winner at the ceremony, Jordan’s name emerged from the envelope. He secured the best actor Oscar for “Sinners,” bringing an end to Chalamet’s lengthy reign as the anticipated victor.
For O’Leary, the outcome meant forfeiting his $1,000 stake. His prediction market gamble on Kalshi came up empty.
Kalshi operates as a regulated platform allowing users to wager on real-world event outcomes. The service has experienced significant growth recently, especially surrounding political races and entertainment industry honors.
O’Leary has used the platform previously and advocated publicly for prediction markets. He’s been an outspoken proponent of the industry’s legitimacy.
The financial hit was minimal for O’Leary, whose wealth reaches into nine figures. Nevertheless, it provided an amusing subplot to his Oscar evening.
O’Leary couldn’t attribute his losing bet to the ballet and opera comments. The voting period had already concluded when that incident occurred.
Jordan’s victory represented the culmination of a impressive awards circuit performance. His SAG triumph had already indicated the race was more competitive than initially believed.
Chalamet did earn recognition with a nomination for his performance in “Marty Supreme.” The production garnered acknowledgment across multiple categories during the ceremony.
O’Leary participated in the event both as an attendee and as part of the film’s ensemble. He made numerous red carpet appearances and conducted interviews with various media outlets ahead of the broadcast.
Kalshi has remained silent regarding betting volume on this year’s best actor category.
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