The 98th Academy Awards may be over, but many are still buzzing about the biggest developments of the night. Of course, there’s been much talk about the 2026 Oscar winners and those who were nominated as well. Timothée Chalamet was one of those many nominees, as he received a Best Actor nod for his performance in Marty Supreme. While Michael B. Jordan ended up winning the award, one of Chalamet’s co-stars, Kevin O’Leary, had a lot of faith in him. So much so that he placed a sizable bet on him to win.
O’Leary – the Canadian businessman who has long appeared on Shark Tank – made his feature film debut in Josh Safdie’s Marty Supreme. Amid awards season, the entrepreneur showed love towards Chalamet and has talked up his performance as ping pong player Marty Mauser. Ahead of this year’s Oscars, O’Leary – who was blinged up for the big night – caught up with Variety and talked up Chalamet. In addition to defending Chalamet against the backlash over those ballet/opera remarks, O’Leary also revealed his bet:
He’s a really great guy. I just put 1000 bucks on Kalshi walking in here that he’s going to win, because I know the voting stops long before that controversy happened. 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.
Now, given that Kevin O’Leary currently has a reported net worth of $400 million, a $1000 bet surely isn’t a big monetary commitment to him. However, for all of us without millions of dollars, that grand is nothing to scoff at. The mere thought of risking so much money on a wager stresses me out a tad as well. Even though the businessman known as “Mr. Wonderful” could likely afford to lose that cash last night, some might be surprised that he initiated the bets given the odds at the time.
Prediction platform Kalshi also posted about O’Leary’s bet and reported that its traders pegged Chalamet as having a 30 percent chance of winning Best Actor. Even ahead of that, entertainment show analysts asserted that Jordan’s chances of winning surged following the Actor Awards. If anything, though, the fact that the SoftKey Software Products founder still put down that money on his co-star is evidence that he had a lot of confidence in him.
In all fairness, O’Leary had reason to feel optimistic, especially throughout the earlier portion of awards season. Timothée Chalamet received praise for his work in Marty Supreme, which also earned strong reviews. As celebrated as Chalamet’s portrayal of Mouser was, it seems more Academy voters preferred Michael B. Jordan’s turn as the Smokestack twins in Sinners.
With Kevin O’Leary’s bet in mind, I now can’t help but wonder what kind of bets were placed on Jordan on Oscar night. That’s not what’s most important, of course, as it’s the art that should ideally matter when it comes to the Academy Awards. All the fiscal aspects of this situation aside, the Best Actor winner was crowned accordingly. I’d also say that, at the end of the day, both Jordan and Chalamet gave performances that’ll surely be discussed for years to come.
Rent or buy Marty Supreme on digital platforms now, and stream Sinners with an HBO Max subscription.
