Monitoring insider trading on Polymarket becomes an activity in its own right

In October 2025, a brand new crypto wallet on Polymarket bet $40,000 that OpenAI would release an AI web browser before the end of the month. The bet turned out to be TRUE shortly after and that account was bringing in $7,000.

As you might guess, this is an incredibly big bet with a suspiciously quick turnaround time.

Insider Finder, a monitoring tool that is part of an analytics software suite from Polymarket called Polysights, detected this transaction in action and posted it to the company’s X account, flagging 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 authorities for punishment, the post was used as a trading signal that helped the account’s followers track the trade and make money from it themselves.

Indeed, for prediction markets like Polymarket, some consider insider trading not only ethically permissible, but pretty much the whole point. Fans of these exchanges claim that gambling is not the only use case for prediction markets, but that any insider action could be used as a signal of certain news before it actually falls. Opponents of this argument say that using nonpublic information to make money on bets can be unfair or potentially fraudulent, and that allowing it only makes rich and powerful insiders richer and more powerful.

“Insider trading only speeds up the discovery of the truth in the end,” said Polysights creator Tre Upshaw. Bloomberg. Upshaw is a 29-year-old former Canadian memecoin trader, and his creation has already amassed 24,000 users and entered the final stages of a $2 million funding round, according to Bloomberg. Even Polymarket gave him a grant of $25,000 to continue his project.

According to the report, approximately 85% of trades reported and published by Upshaw on

Polymarket was banned in the United States in 2022 under the Biden administration for failing to obtain approval from the Commodity Futures Trading Commission before allowing customers to purchase event-based contracts, in other words: make bets around yes or no questions based on real possibilities. President Trump first finished the probes in the Peter Thiel-backed company in July 2025. Shortly after, Polymarket announced its big return to the United States (although not yet fully operational), and that Trump’s son, Donald Trump Jr., was joining the company as advise.

Insider trading is strictly prohibited in traditional finance. But in the Wild West of underregulated prediction markets, it is coveted. And OpenAI isn’t the only company under scrutiny because would-be insiders are using Polymarket to make a quick buck. A potential Google intern earned more than a million dollars last year, betting on Google’s 2025 Year in Search ranking hours before its reveal.

The CFTC, which regulates the similar prediction market platform Kalshi and has green light Polymarket Re-entry currently has no guidance on insider trading in prediction markets. Meanwhile, Trump is notoriously supportive of prediction markets. Trump Media is even launching its own Polymarket-style prediction marketplace on Trump’s social media platform, Truth Social.

But regardless of Trump’s support, prediction markets, and especially insider trading on these platforms, are under greater scrutiny than ever. It all started earlier this month, when a brand new Polymarket account bet $30,000 and reportedly won $436,759 on the fall of Venezuelan President Nicolás Maduro in a few hours.

Following this incident, New York Democratic Representative Ritchie Torres introduced a bill prohibiting federal officials from betting on political outcomes in prediction markets. It is unclear whether or not this bill will pass, but it had 30 co-sponsors as of Monday, all Democrats.