TLDR
- The Shark Tank investor wagered $1,000 through Kalshi prediction market backing Timothée Chalamet for the best actor Oscar
- O’Leary appears alongside Chalamet in “Marty Supreme,” portraying business magnate Milton Rockwell
- Despite early frontrunner status, Chalamet’s Oscar chances weakened following backlash over remarks about ballet and opera
- The best actor Academy Award went to Michael B. Jordan for his role in “Sinners”
- While O’Leary pointed out Academy voting concluded before the controversy erupted, the outcome remained unchanged
Kevin O’Leary arrived at the Academy Awards with more than formal attire. The business mogul and television personality had financial stakes in one of the evening’s most anticipated categories.
In a conversation with Variety on the red carpet, O’Leary disclosed he’d placed a $1,000 wager through Kalshi, a prediction market platform. His bet? That Timothée Chalamet, his fellow cast member from “Marty Supreme,” would claim the best actor trophy.
The business reality show star appears in “Marty Supreme” as Milton Rockwell, a wealthy tycoon character, while Chalamet carries the leading role.
For much of awards season, Chalamet was viewed as the clear favorite to win. However, the final weeks saw a dramatic change in the competitive landscape.
Backlash and Changing Dynamics
Weeks before the ceremony, Chalamet sparked controversy during a public appearance. He made disparaging remarks about ballet and opera, characterizing them as art forms attempting to preserve traditions “even though no one cares about this anymore.”
The entertainment and arts communities reacted negatively to these statements. Questions arose about whether the fallout might influence Academy members’ voting decisions.
Speaking to reporters, O’Leary downplayed such concerns. He emphasized that Academy voting had concluded well before the controversy gained traction.
“I know the voting stopped long before that controversy happened,” O’Leary told Variety.
His observation was technically accurate. The chronology supported his reasoning. However, the final results painted a different picture entirely.
Michael B. Jordan had been building momentum throughout the awards circuit. His compelling work in “Sinners” earned him the Screen Actors Guild Award for best actor, a ceremony held prior to the Oscars.
Industry observers viewed that SAG triumph as significant. Since SAG voters are actors who largely overlap with Oscar voters, the win suggested shifting sentiment.
Jordan Emerges Victorious
When presenters revealed the winner during the broadcast, Jordan’s name was called. He secured the best actor Oscar for “Sinners,” concluding Chalamet’s months-long status as the anticipated victor.
The outcome meant O’Leary’s $1,000 prediction market bet came up short. His Kalshi wager yielded no return.
Kalshi operates as a federally regulated prediction market where participants can place bets on various real-world outcomes. The platform has experienced significant growth recently, especially regarding political elections and entertainment industry awards.
O’Leary has publicly utilized the platform before and advocated for prediction market legitimacy. He’s been among the more prominent voices supporting this emerging industry.
Given O’Leary’s estimated net worth in the hundreds of millions, the thousand-dollar loss represented a minimal financial impact. Nevertheless, it provided an interesting footnote to his Oscar evening experience.
The investor couldn’t attribute Chalamet’s defeat to the ballet and opera backlash. Academy members had already submitted their ballots before the comments generated headlines.
Jordan’s victory represented the culmination of an impressive awards season campaign. His SAG Award had already demonstrated the race was more competitive than initial projections suggested.
Chalamet did earn recognition through his best actor nomination for “Marty Supreme.” The production received acknowledgment across multiple Oscar categories during the ceremony.
O’Leary participated in the event both as an industry guest and as part of the film’s ensemble. He engaged with numerous media representatives while making his way down the red carpet.
Kalshi has not released information regarding the total betting volume on this year’s best actor competition.
