TLDR
- Kevin O’Leary bet $1,000 on prediction market app Kalshi that his “Marty Supreme” costar Timothée Chalamet would win the best actor Oscar
- O’Leary plays tycoon Milton Rockwell in “Marty Supreme” alongside Chalamet
- Chalamet had been the frontrunner for best actor but lost momentum after controversial comments about ballet and opera
- Michael B. Jordan won the best actor Oscar for “Sinners,” beating Chalamet
- O’Leary noted that Oscar voting closed before the Chalamet controversy, but it didn’t matter in the end
Kevin O’Leary showed up to the Oscars red carpet with more than just a tuxedo. The “Shark Tank” star had money riding on the outcome of the best actor category.
O’Leary told Variety that he placed a $1,000 bet on the prediction market app Kalshi. He wagered that his “Marty Supreme” costar Timothée Chalamet would take home the best actor prize.
The two worked together on “Marty Supreme,” where O’Leary plays a character named Milton Rockwell, a tycoon. The film stars Chalamet in the lead role.
Chalamet had been widely considered the frontrunner for the award for much of the season. That changed in recent weeks as momentum shifted.
Chalamet’s Controversy and Shifting Odds
Earlier this month, Chalamet made comments at an event that drew backlash. He said he didn’t want to work in ballet or opera, calling them art forms where the attitude is to keep something alive “even though no one cares about this anymore.”
The remarks did not sit well with many in the arts community. Some wondered whether the controversy would hurt his chances with Oscar voters.
O’Leary dismissed that concern on the red carpet. He pointed out that Oscar voting had already closed before the comments became a story.
“I know the voting stopped long before that controversy happened,” O’Leary told Variety.
He had a point. The timeline did back up his argument. But the voting results told a different story.
Michael B. Jordan had already been gaining ground in the race. His performance in “Sinners” earned him the best actor prize at the SAG Actor Awards, which took place before the Oscars.
That SAG win was seen as a turning point. The award is voted on by actors, and many of those same actors also vote for the Oscars.
Jordan Takes Home the Oscar
When the envelope was opened at the ceremony, it was Jordan’s name inside. He won the best actor Oscar for “Sinners,” ending Chalamet’s long run as the presumed winner.
For O’Leary, it meant losing his $1,000 bet. The prediction market wager on Kalshi did not pay off.
Kalshi is a regulated prediction market platform where users can bet on the outcomes of real-world events. It has grown in popularity in recent years, particularly around elections and entertainment awards.
O’Leary is a known user of the platform and has spoken publicly about prediction markets before. He has been a vocal supporter of the prediction market industry.
The loss was a small one for O’Leary, whose net worth is estimated in the hundreds of millions. But it added a layer of entertainment to his Oscar night appearance.
O’Leary could not point to the ballet and opera controversy as the reason for the loss. The votes were already in before that story broke.
Jordan’s win capped off a strong awards season run. His SAG victory had already signaled that the race was tighter than many had expected.
Chalamet still received a nomination for his work in “Marty Supreme.” The film was recognized in several categories at the ceremony.
O’Leary attended the event as both a guest and a cast member of the film. He walked the red carpet and spoke to multiple outlets before the show.
Kalshi has not commented on the volume of bets placed on the best actor category this year.
