Oscars Night: The Real Winner Is Kalshi?

By Jason Brett, Forbes

Translated by Saoirse, Foresight News

Kevin O’Leary—“Mr. Wonderful” from the reality show Shark Tank—made an appearance on the red carpet of the 98th Academy Awards at the Dolby Theatre in Los Angeles.

The investor later publicly announced that he had personally wagered $1,000 on Kalshi to bet on Timothée Chalamet winning Best Actor.

Image source: Getty Images

On the evening of March 15, U.S. time, the 98th Academy Awards ceremony was held at the Dolby Theatre in Los Angeles. Yet beyond this star-studded event, one platform stole the spotlight—Kalshi.

While Conan O’Brien hosted ABC and Hulu’s live broadcast of the awards, traders on Kalshi and Polymarket collectively placed over $120 million in bets on Oscar-related prediction contracts—an all-time record for regulated prediction markets during awards season. This surge was propelled by a landmark advisory opinion and proposed regulatory framework released three days earlier by the U.S. Commodity Futures Trading Commission (CFTC).

Kalshi alone accounted for more than $58 million in trading volume—and that figure continued rising in real time throughout the ceremony. Polymarket contributed the remainder, pushing the total to over $120 million. That amount is roughly six to seven times Kalshi’s entire awards-season trading volume last year, representing a massive leap forward compared to 2025.

Elisabeth Diana, Kalshi’s Head of Communications, told me via email: “The Oscars are so popular on prediction markets because they represent the ultimate test of the ‘wisdom of crowds.’”

Numerous celebrities also joined in. On the Oscar red carpet that night, Kevin O’Leary—star of Shark Tank and co-star of Timothée Chalamet’s film *A Complete Unknown* (also known as *Wolfs*)—publicly announced he had personally wagered $1,000 on Kalshi betting Chalamet would win Best Actor. This move was entirely organic, with no commercial partnership, paid promotion, or prior arrangement.

Kalshi’s fund flows clearly reveal where the big money concentrated:

• Best Actor: ~$25 million (the most competitive category—and the one Kevin O’Leary bet on);
• Best Picture: ~$24 million (market sentiment favored *The Brutalist*);
• Best Director: ~$7 million;
• Best Supporting Actor and Best Supporting Actress: ~$5 million each.

That night, the wisdom of crowds shone brilliantly—even weaving itself into the ceremony itself.

In his opening monologue, host Conan O’Brien jokingly referenced artificial intelligence and Timothée Chalamet’s controversial February remarks about ballet and opera. That incident briefly flipped Kalshi’s Best Actor odds—until traders remembered that Oscar voting had already closed, prompting the market to correct itself.

Similar real-time price fluctuations unfolded across every award category, transforming passive viewers into active participants viewing the event through a market lens.

The timing of this explosion could not have been more perfect. The CFTC’s staff advisory opinion and notice of proposed rulemaking, issued on March 12, provided registered platforms like Kalshi with a clear federal regulatory pathway. Traders finally gained the long-awaited regulatory certainty—and responded with record-breaking trading volume.

Kalshi’s integration with Rotten Tomatoes and its intuitive mobile app made participation easier than ever for everyday users. The result? Oscar Night is no longer just about red carpets and acceptance speeches—it has become a regulated, data-driven spectacle where the wisdom of crowds collides with Hollywood glamour.

As the final awards were unveiled one by one, each envelope opening triggered immediate market reactions. Whether *The Brutalist* swept the major categories—or a surprise upset occurred—one thing is now crystal clear:

The true winner of the 2026 Oscars is the compliant prediction market—and its explosive growth.