In October 2025, a brand new crypto wallet on Polymarket bet $40,000 that OpenAI would launch an AI web browser before the end of the month. The bet turned out to be true shortly after and that account made $7,000.
As you can guess, that’s a shockingly big bet with a suspiciously quick turnaround.
Insider Finder, a monitoring tool that is part of a Polymarket analytics software suite called Polysights, caught this trade in action, and posted it on the company’s X account, flagging the user as a potential insider with direct knowledge of the web browser launch. But as opposed to any other market where insider trading would be reported to the authorities for punishment, the post was used as a trading signal that helped the account’s followers to follow the trade and make money off of it themselves.
That’s because for prediction markets like Polymarket, insider trading is deemed by some to be not just ethically allowed but pretty much the entire point. Fans of these exchanges claim that gambling is not the only use case of prediction markets, but that any insider action could be used as a signal of certain news before it actually drops. Opponents to that argument say that using non-public information to make money on bets can be unfair or potentially fraudulent, and allowing it only stands to make rich and powerful insiders richer and more powerful.
“Insider trading just accelerates the truth faster at the end of the day,” the creator of Polysights, Tre Upshaw, told Bloomberg. Upshaw is a 29-year-old former memecoin trader from Canada, and his creation has already amassed 24,000 users and entered the final stages of a $2 million funding round, per Bloomberg. Even Polymarket has given him a $25,000 grant to pursue it.
Roughly 85% of the trades that Upshaw flagged and posted on X were winning, the report says, and Upshaw himself wagers hundreds of dollars of his own money for trades that he feels confident in.
Polymarket was banned in the United States in 2022 under the Biden administration for failing to get approval from the U.S. Commodity Futures Trading Commission before letting customers buy event-based contracts—in other words: make bets around yes-or-no questions based on real life possibilities. President Trump first ended the probes into the Peter Thiel-backed company in July 2025. Shortly after, Polymarket announced it’s grand return to the U.S. (though its still not fully operational yet), and that Trump’s son Donald Trump Jr. was joining the company as adviser.
Insider trading is strictly banned in traditional finance. But in the wild west of under-regulated prediction markets, it’s coveted. And OpenAI isn’t the only company under scrutiny for having potential insiders using Polymarket to make quick cash. A potential Google insider made more than a million dollars last year betting on Google’s 2025 Year in Search rankings hours before they were revealed.
The CFTC, which regulates similar prediction market platform Kalshi and has greenlit Polymarket’s re-entry, does not currently have any guidance on insider trading on prediction markets. Meanwhile, Trump is notoriously pro-prediction markets. Trump Media is even launching a Polymarket-like prediction market of its own on Trump’s social media platform Truth Social.
But regardless of Trump’s support, prediction markets and specifically insider trading on these platforms has been receiving more scrutiny than ever before. It all started earlier this month, when a brand new Polymarket account bet $30,000 and reportedly gained $436,759 on Venezuelan president Nicolás Maduro’s downfall in a matter of hours.
Following that incident, New York Democratic Rep. Ritchie Torres introduced a bill making it illegal for federal officials to bet on policy outcomes on prediction markets. It’s not certain whether or not that bill will pass, but it does have 30 co-sponsors as of Monday, all Democrats.
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