Suspiciously timed Polymarket bets before the Maduro raid spur fresh insider-trading scrutiny
An anonymous trader turned roughly US$34,000 into nearly US$410,000 by betting on Nicolás Maduro’s downfall.
The trade was placed just hours before a secret US military raid and now sits at the centre of a fast‑moving debate over whether prediction markets have become an unpoliced channel for monetizing inside information.
According to AP News, a newly created account on crypto‑based prediction platform Polymarket placed just 13 bets between December 27 and January 3, all tied to the US invading Venezuela or Maduro being out of office by January 31.
The trader’s final wager came at 9:58 pm ET on January 2, when contracts implying only an 8 percent chance of Maduro losing power that month traded at about 8 cents.
NBC News reported that US President Donald Trump ordered the military to move forward with a special operation to capture Maduro and his wife at 10:46 pm ET.
Explosions rocked Caracas around 1:00 am on January 3, and by 8:41 am the trader started cashing out, ultimately locking in close to US$410,000 in profit.
AP News noted that more than half of the capital went in on the evening before the attack.
Tre Upshaw, founder of analytics firm Polysights, said “it’s more likely than not that this was an insider,” calling it “a lot of money to put in at that price, without a lot of news.”
NBC News reported that US officials said Trump had decided before Christmas to authorise the operation but kept the timing fluid and tightly held among a small circle of advisers.
AP News added that the mission required coordination across military branches and 150 warplanes flying from 20 locations in the Western Hemisphere.
Despite that, the trader did not appear to make much effort to cover their tracks.
A spokesperson for Chainalysis told NBC News that the bettor already cashed out their winnings in Solana through a major American exchange, with no obvious attempt to hide or launder funds, and that regulators or law enforcement would likely have “little difficulty” finding them.
The case lands squarely in a regulatory grey zone.
Insider trading in equities and many derivatives is clearly illegal, and regulators routinely examine suspicious trades ahead of major announcements. But the legal framework is less tested for prediction markets, which package “yes/no” bets as “event contracts.”
If the Maduro trader were a US official misusing government information, they could face charges under existing rules that treat insider trading in swap contracts as illegal, said Noah Solowiejczyk of Fenwick & West, as reported by AP News.
He added that if the trader is a foreign national who bet from abroad, US authorities might lack jurisdiction.
David Chase, a former Securities and Exchange Commission lawyer now working as a securities defence attorney, told NBC News that using inside information for an edge in commodities trading is generally considered fraud.
He said courts “are going to have to catch up” when it comes to applying that logic to prediction platforms.
According to AP News, prediction markets such as Polymarket sit under the US Commodity Futures Trading Commission (CFTC) rather than state gambling regulators, allowing them to avoid the patchwork of state betting rules.
Karl Lockhart, a law professor at DePaul University, called this “a huge loophole,” saying platforms only need to comply with a single federal regime.
Polymarket previously reached a 2022 settlement with the CFTC that barred it from operating in the US under President Joe Biden’s tougher stance.
NBC News reported that the CFTC later dropped a probe and, late last year under Trump, approved Polymarket to operate as a US exchange.
AP News said the platform has started rolling out options for Americans, even as new users still must attest that they are not US persons or physically in the US.
The Maduro trade is not Polymarket’s only controversy.
AP News reported that an account labelled “0xafEe” made about US$1.2m on bets about Google’s most‑searched people in 2025 and previously earned more than US$100,000 by correctly predicting the release date of Google’s Gemini 3 AI model, prompting some observers to dub the user a “Google insider.”
Google did not respond to a request for comment cited by AP News.
The political response is now catching up.
Democratic Representative Ritchie Torres introduced a bill aimed at restricting government employees’ participation in politically related event contracts, specifically in light of concerns around the Maduro trades.
NBC News said Torres plans to advance the Public Integrity in Financial Prediction Markets Act of 2026, which would explicitly criminalise using non‑public information on such sites.
Kalshi CEO Tarek Mansour supports the push, according to AP News, saying insider trading has always been banned on his regulated event‑contract exchange but arguing that more must be done to rein in unregulated markets.
