The Journal. Insiders Are Cashing In on Prediction Markets
185 snips
Feb 17, 2026 
Caitlin Ostroff, an investigative reporter at The Wall Street Journal who covers tech and markets, digs into booming prediction markets. She walks through suspicious big halftime bets, how Polymarket and Kalshi operate, and traders making huge profits. The conversation probes insider-information risks, regulatory gray areas, and how platforms might tighten controls.
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Super Bowl Trader's Perfect Run
- A single Polymarket user placed 19 Super Bowl halftime bets and won nearly $17,000 after 17 correct picks.
- The account traded only around the Super Bowl window and showed no other activity, suggesting prior knowledge or extreme luck.
Alpha Raccoon's Google Windfall
- An account called Alpha Raccoon made nearly $1 million betting on Google product dates and top search terms.
- The trader correctly guessed 22 of 23 top search terms and exact release timing for a new AI model.
Sensitive Geopolitical Bets Paid Off
- Traders profited hundreds of thousands by betting on Israel-Iran strikes and on Maduro being ousted.
- Israeli authorities arrested reservists linked to some bets, and one account reportedly made $400,000 around Venezuela events.