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When U.S. Delta Force commandos slipped into Venezuelan airspace over the weekend, they did so in secrecy. And yet, in the hours before President Donald Trump gave the final order for the strike, someone bet more than $20,000 that Nicolás Maduro would be ousted as the country’s leader by the end of January.
On Polymarket, the online platform that lets people wager on almost anything, an anonymous trader somewhere in the world placed a series of suspiciously well-timed bets. Using a fresh account created last month, the individual made just a few bets in the days leading up to the raid, according to The Wall Street Journal—all on the possibility of imminent regime change in Venezuela—and appeared to come away with more than $400,000.
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Perhaps the bettor just got phenomenally lucky. Or perhaps they knew about the raid ahead of time and leveraged it for a quick payout. We can’t know, because Polymarket, a so-called prediction market where people turn their idle hunches into real cash, allows some of its customers to remain anonymous. Traders place their bets using crypto, which could provide another layer of cover. The Maduro trade has generated a huge amount of speculation and controversy; the internet is now full of jokes that Barron Trump, hunched behind dual monitors in his NYU dorm room, may have been behind it.
This is not the first instance of a well-timed bet on Polymarket raising questions about insider trading. Just before María Corina Machado, a leader of Venezuela’s opposition to Maduro, was declared the winner of the 2025 Nobel Peace Prize, the probability that she would win the award began to spike on Polymarket (despite a highly secretive selection process). The Nobel Institute has said that it may have been a victim of espionage. Early last month, a trader made a series of bets related to Google’s most popular searches of 2025. Just before the company released its “Year in Search” report, the user bet on some of those top searches with uncanny accuracy. In the end, the account netted more than $1 million.
Traditional financial markets have clear-cut rules around insider trading: Capitalizing on nonpublic information is plainly illegal. Polymarket seems to have no suchpolicies in its terms of use (although it does ban activity that violates “applicable laws”). The company’s CEO, Shayne Coplan, has also explicitly said that Polymarket creates a “financial incentive for people to go and divulge” new information. The thinking is that, if the function of these tools is to predict the future, then rewarding people for leaking information could be seen as a positive. When insiders push markets toward what’s actually going to happen, they can hypothetically turn prediction markets into a source of real-time unfiltered news. There are legal ways to find and divulge new information—say, in scraping publicly available data for an edge over other traders—but Coplan did not draw that distinction. (Polymarket did not respond to a request for comment.)
Not all prediction markets share this ethos. Kalshi, Polymarket’s biggest competitor, “explicitly prohibits insider trading of any form,” a spokesperson told me over email. But the concept of treating insider trading as a feature rather than a bug seems to be gaining traction. Brian Armstrong, the CEO of Coinbase—a cryptocurrency exchange that recently purchased a prediction-market firm—laid out this line of thinking at The New York Times’ DealBook Summit last month: “If your goal is actually for the 99 percent of people trying to get signal about what’s going to happen in the world—like, ‘Is the Suez Canal going to be reopened?’ or whatever—you actually want insider trading.”
Outsourcing privileged information to prediction markets in the name of “news” has some clear problems. Maduro’s ouster is a helpful example: Both the Times and The Washington Post reportedly learned of the plans for Saturday’s raid before it happened, and held off on publishing their stories to avoid endangering U.S. troops. No such editorial-judgment calls are being made across betting markets. The democratization of certain kinds of information can be a social good—but not like this.
As it becomes easier for people to bet on everyday phenomena, more opportunities will open up for insiders to leverage private information for fast cash. Hypothetically, the Deloitte employees who tabulate Grammy votes can bet on who might win Song of the Year, and the White House aide with a sense of the president’s mood can bet on whether he’ll publicly use the word fuck before the end of the month. It’s no secret that these markets can be gamed. Armstrong closed Coinbase’s most recent earnings call with a string of non sequiturs (“Bitcoin, ethereum, blockchain, staking, and Web3”) in a nod to the traders betting on whether those specific words would crop up during the call.
Polymarket has become enormously popular, even though its main platform isn’t meant to be accessed from within the United States. In 2022, the company shut down its domestic service as part of a settlement with the Biden administration over alleged regulatory violations. Still, American bettors have found an easy work-around in the digital trickery of VPNs, or virtual private networks. Polymarket is now gearing up for a U.S. comeback, with the support of the new White House. The company tapped a former Trump campaign manager to lobby on its behalf last year, and Donald Trump Jr. now serves as an adviser to both Polymarket and Kalshi. The Trump family’s media company is working on a prediction market too: Truth Predict.
Insider trading is frowned upon because it further slants an already uneven playing field, further enriching those in proximity to the biggest and most consequential decisions of the day and leaving the public at a disadvantage. This, at least, has been the prevailing view for much of the modern history of American commerce. Traditional financial markets aren’t always fair, but they at least purport to operate from a shared perspective. Among the central innovations of prediction markets is the idea that an unequal playing field might actually facilitate the truth. It’s a convenient line. But it obscures the fact that these are still very much also just markets. When insiders win, the rest of us lose.
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