Oscar Night, The Real Winner Is Kalshi?

Oscar Night Turns into a Regulated, Data-Driven Event Where Collective Intelligence Meets Hollywood Glamour

By: Jason Brett, Forbes

Translated by: Saoirse, Foresight News

Reality TV star Kevin O’Leary, known as “Mr. Wonderful,” appeared on the red carpet at the 98th Academy Awards at the Dolby Theatre in Los Angeles.

The investor later publicly announced that he personally wagered $1,000 on the Kalshi platform, betting on Timothy Chalamet to win Best Actor.

Image source: Getty Images

On the evening of March 15, local time, the 98th Academy Awards took place at the Dolby Theatre in Los Angeles. Outside the ceremony, one platform has already stolen the spotlight — it’s Kalshi.

While Conan O’Brien hosted the award show live on ABC and Hulu, traders on the two major platforms, Kalshi and Polymarket, had already invested over $120 million in Oscar-related contracts. This marks the largest betting surge in a regulated prediction market during awards season in history. Driving this was a milestone guidance and regulatory rule issued just three days earlier by the U.S. Commodity Futures Trading Commission (CFTC).

Kalshi alone saw trading volume surpass $58 million, and it continued to rise in real-time during the ceremony; Polymarket contributed the remaining volume, pushing the total past $120 million. This figure is roughly 6 to 7 times the total trading volume of Kalshi during last year’s awards season, representing a significant leap compared to 2025.

Kalshi’s PR director, Elisabeth Diana, told me via email: “The reason Oscar betting is so hot in the trading market is because it’s the ultimate test of ‘collective intelligence.’”

Many celebrities also participated personally. On the red carpet that night, reality TV star Kevin O’Leary — who also appeared in Timothy Chalamet’s film “The King of Staten Island” (also known as “The Big Short”) — publicly announced that he personally bet $1,000 on Kalshi, wagering on Chalamet to win Best Actor. This was entirely spontaneous, with no commercial partnership, paid promotion, or prior arrangement.

The flow of funds on the Kalshi platform clearly shows concentrated betting on certain awards:

• Best Actor: about $25 million (the most competitive category, also the one Kevin O’Leary bet on);
• Best Picture: about $24 million (market favors “All Quiet on the Western Front”);
• Best Director: about $7 million;
• Best Supporting Actor and Actress: each about $5 million.

This collective intelligence was vividly demonstrated that night, even integrating into the award ceremony itself.

Host Conan O’Brien, in his opening monologue, joked about artificial intelligence and Timothy Chalamet’s controversial comments on ballet and opera in February. This incident once shifted the odds for Chalamet’s Best Actor win until traders remembered that Oscar voting had already closed, prompting the market to readjust.

Similar real-time price fluctuations played out across each award category, turning passive viewers into active participants who engaged with the market perspective in real time.

The timing of this explosion was perfect. The CFTC’s staff guidance and proposed rules, announced on March 12, provided a clear federal regulatory pathway for legitimate registered platforms like Kalshi. Traders finally gained the long-awaited regulatory certainty and responded with record-breaking trading volumes.

Kalshi’s integration with Rotten Tomatoes reviews and its simple, user-friendly mobile app made it easier than ever for the general public to participate. As a result, Oscar Night is no longer just about red carpets and acceptance speeches; it has become a regulated, data-driven event where collective intelligence collides with Hollywood glamour.

As the final few awards are announced one by one, each envelope opened in real time influences market movements. Whether “All Quiet on the Western Front” sweeps the awards or a surprise upset occurs, one thing is clear:

The true winner of the 2026 Oscars will be the compliant prediction markets experiencing explosive growth.