Less than five hours before nighttime explosions rocked the Venezuelan capital of Caracas, an unknown trader doubled down on bets that Nicolás Maduro would soon be out as the country's leader.
The wagers on Polymarket, a popular crypto-based betting platform, netted the trader more than $400,000, a 12-fold return on investment -- and fueled suspicions that someone used inside knowledge of the closely held U.S. operation to make a quick profit.
Insider trading is illegal in the stock market, and regulators routinely monitor suspicious trades ahead of big corporate news so they can prosecute insiders who attempt to enrich themselves using nonpublic information.
There are fewer safeguards in place to prevent people from exploiting their inside knowledge on Polymarket. The site allows users to bet on a variety of future events, ranging from President Trump's political appointments to this year's World Cup to which characters would die in the recent season of "Stranger Things."
The anonymous user created an account last month and placed an initial bet on Dec. 27, buying $96 worth of contracts that would pay off if the U.S. invaded Venezuela by Jan. 31, Polymarket data shows. The person ramped up bets over the next week, sticking to a handful of similar contracts, as tensions mounted between Washington and Caracas.
The trader focused bets on contracts that would pay out if Maduro would no longer be Venezuela's leader by Jan. 31, when that still seemed like a long shot.
The trader's final bet came at 9:58 p.m. ET on Friday, shortly before President Trump ordered the military to move forward. Such contracts were priced at just 8 cents apiece, implying that Polymarket users saw only an 8% probability of the Venezuelan strongman losing power this month, the platform's data shows.
Several hours later, news broke of the U.S. operation to capture Maduro and the contracts shot up in value. In the end, the trader earned nearly $410,000 in profit on about $34,000 worth of wagers. More than half the value of the total wager was placed the evening before the attack.
The concentrated nature of the bets, in a brand-new account, when there was little public news pointing specifically to an imminent ouster of Maduro are all potential indicators of an insider, longtime Polymarket watchers said. The trader goes by a default screen name made up of a blockchain address, a long string of numbers and letters.
"It's more likely than not that this was an insider. That's a lot of money to put in at that price, without a lot of news," said Tre Upshaw, founder of Polysights, a startup that provides analytics tools for Polymarket traders, including a feature to flag potential insider activity.
If the trader behind the Maduro bets was a U.S. official who misused government information, the trader could be prosecuted under existing laws against insider trading in swap contracts, said Noah Solowiejczyk, a partner at law firm Fenwick & West. But if the trader was a foreigner who placed the trades abroad, U.S. authorities might not have a case because of a lack of jurisdiction, he added.
The Trump administration kept the plan closely held within a small circle of top advisers to protect the element of surprise, according to reporting by The Wall Street Journal. The operation required cooperation across military branches, and 150 warplanes flew from 20 locations throughout the Western Hemisphere.
Following news of the Maduro bets, Rep. Ritchie Torres (D., N.Y.) said he plans to introduce a bill this week to explicitly prohibit federal elected officials, political appointees and executive-branch employees from betting in prediction markets where they have relevant nonpublic information or could obtain it.
In theory, Polymarket prohibits Americans from using its main betting platform. But in practice, traders circumvent the ban by using VPNs, or virtual private networks, to mask which country they are from.
Polymarket has been hit with repeated controversies in recent months about potential insider trading.
In December, a trader with the account "0xafEe" made $1.2 million with a set of accurate bets on Google's most-searched people in 2025, Polymarket data shows.
The same trader previously earned more than $100,000 by correctly betting on the release date of Google's Gemini 3 AI model. Some Polymarket watchers dubbed the trader the "Google insider" and suggested that the bets were based on nonpublic information. Google didn't respond to a request for comment.
Solowiejczyk, a former federal prosecutor, predicted that insider trading on prediction markets would draw more scrutiny as the platforms gain popularity.
"Given how prevalent these incidents seem to be and how they are getting a lot of attention, I tend to think that eventually it is very likely we will see one of these cases," he said.
In an interview in December, before the controversy over the Maduro bets, Polymarket founder and chief executive Shayne Coplan said a form of self-regulation had emerged on the platform. He noted that traders monitor real-time data to spot potential insiders and tend to avoid contracts that appear prone to insider trading.
Shayne Coplan, CEO of Polymarket, on the floor of the NYSE.
"The moment there is a suspected insider, it's pointed out on X, and it's visible on Polymarket immediately. So it's not like it's done in darkness," Coplan told The Wall Street Journal.
Polymarket has the ability to conduct internal audits to examine allegations of insider trading, a person familiar with the matter said. Past audits have usually found that the traders behind the suspicious activity weren't true insiders, but instead obtained information via legal means, such as scraping websites for clues of a coming announcement, the person added.
