MAGA Host Makes Last Minute Oscar Bet on Controversial Co-Star

MONEY TALKS

The “Shark Tank” host’s latest investment is in his Oscar nominated costar.

Shark Tank host Kevin O’Leary is wearing his investments on his sleeve—and around his neck.

While sporting a one-of-one necklace he values at $30 million, O’Leary, 71, backed his Marty Supreme co-star, Timothée Chalamet, morally and financially.

“He’s a really great guy,” the Shark Tank host told Variety of the Oscar nominee. “The kid is a great kid. He took a bum rap on that. And by the way, gave a lot of promo to opera houses and ballet.”

“I just put $1,000 on Kalshi walking in here that he’s going to win, because I know the voting stops long before that controversy happened,” O’Leary added.

Timothée Chalamet, winner of the Best Actor Award for "Marty Supreme", speaks onstage during the 31st Annual Critics Choice Awards at Barker Hangar on January 04, 2026 in Santa Monica, California.
Timothée Chalamet, winner of the Best Actor Award for "Marty Supreme", speaks onstage during the 31st Annual Critics Choice Awards at Barker Hangar on January 04, 2026 in Santa Monica, California. Kevin Winter/Getty Images for Critics Choice Association

Last week, the Oscars’ Best Actor race was thrown into disarray when Chalamet’s controversial comments about ballet and opera resurfaced from a joint town hall with Oscar winner Matthew McConaughey.

“I don’t want to be working in ballet, or opera, or things where it’s like, ‘Hey, keep this thing alive, even though like no one cares about this anymore,’” Chalamet, 30, said during the February town hall in a discussion about the future of cinema. “All respect to the ballet and opera people out there...”

“I just lost 14 cents in viewership. I’m taking shots for no reason,” he continued.

After Chalamet started the awards season strong with back-to-back wins at the Golden Globes and Critics’ Choice Awards, he has since lost out at the BAFTAs and Actor Awards.

Kevin O’Leary and Timothée Chalamet
Kevin O’Leary and Timothée Chalamet in "Marty Supreme." A24

Though the Best Actor nominee was strongly rebuked by the arts community, the Oscar voting window closed on March 5, days before Chalamet’s comments drew widespread attention. It is not likely that his comments had any impact on voting.

After Sinners star Michael B. Jordan beat Chalamet at the Actor Awards, the category’s odds flipped on Kalshi. Jordan, 39, is now a 59% favorite, with Chalamet trailing at 32%. O’Leary stands to earn just over $3,000 if his Marty Supreme co-star takes home his first golden statue.

Michael B. Jordan
Michael B. Jordan at the 32nd Annual Actor Awards Presented by SAG-AFTRA held at Shrine Auditorium and Expo Hall on March 01, 2026 in Los Angeles, California. (Photo by Michael Buckner/Variety via Getty Images) Michael Buckner/Variety via Getty Images

Chalamet has previously been nominated twice, for Call Me By Your Name and A Complete Unknown. His film, Marty Supreme, is nominated for nine Academy Awards, including Best Picture, Best Original Screenplay, and Best Casting—a new category.

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