As you can guess, this is a shockingly big bet with a suspiciously quick turnaround.
Insider Finder, a monitoring tool that is part of the Polymarket analytics software suite called Polysites, caught this trade in action, and posted it to the company’s X account, marking the user as a potential insider with direct knowledge of the web browser launch. But unlike any other market where insider trading would be reported to the authorities to punish them, the post was used as a trading signal that helped followers of the account follow the trades and make money themselves.
This is because for prediction markets like PolyMarket, insider trading is considered by some to be not only morally permitted, but almost a complete issue. Fans of these exchanges claim that gambling is not the only use case of prediction markets, but any insider action can be used as a signal of some news before it actually falls. Opponents of that argument say that using non-public information to make money at stake could be unfair or potentially fraudulent, and that it is only allowed to make rich and powerful insiders richer and more powerful.
“Insider trading exponentially overstates the truth at the end of the day,” Trey Upshaw, creator of Polysites, told Bloomberg. According to Bloomberg, Upshaw is a 29-year-old former Memecoin trader from Canada and his creation already has 24,000 users and has entered the final stages of a $2 million funding round. Polymarket has even given them a grant of $25,000 to pursue it further.
The report states that about 85% of the trades marked by Upshaw and posted on X were winning, and Upshaw himself bets hundreds of dollars of his own money on trades in which he feels confident.
PolyMarkets was banned in the United States under the Biden administration in 2022 for failing to obtain approval from the US Commodity Futures Trading Commission before allowing clients to buy event-based contracts – in other words: Bet on yes-or-no questions based on real-life probabilities. President Trump first ended his investigation of the Peter Thiel-backed company in July 2025. Shortly after, Polymarket announced its grand return to the US (although it is still not fully operational), and Trump’s son Donald Trump Jr. is joining the company as an advisor.
Insider trading is strictly prohibited in traditional finance. But in the Wild West of less-regulated prediction markets, it is coveted. And OpenAI isn’t the only company whose potential insiders are under scrutiny for using Polymarket to make quick cash. A would-be Google insider made more than a million dollars last year by betting on Google’s 2025 search rankings just hours before they were revealed.
The CFTC, which regulates similar prediction markets platform Kalshi and greenlighted PolyMarket’s re-entry, currently has no guidance on insider trading on prediction markets. Meanwhile, Trump is notoriously pro-market. Trump Media is also launching a PolyMarket-like prediction market of its own on Trump’s social media platform, Truth Social.
But despite Trump’s support, prediction markets, and especially insider trading on these platforms, are receiving more scrutiny than ever. It all started earlier this month, when a brand new Polymarket account bet $30,000 and reportedly made a profit of $436,759 on the fall of Venezuelan President Nicolas Maduro in just a few hours.
Following that incident, New York Democratic Representative Ritchie Torres introduced a bill making it illegal for federal officials to bet on policy outcomes on prediction markets. It’s not certain whether that bill will pass, but as of Monday it has 30 co-sponsors, all Democrats.
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