Point, kill, and cash in: Trump’s men bet on their own crimes
On the morning of Feb. 28, an anonymous account on Polymarket placed a $20,000 bet that Iranian Supreme Leader Ali Khamenei would be dead by the end of March. Hours later, he was. Killed in the American–Israeli airstrike on Tehran. The account netted $120,000. If it were an exception, you could call it luck.
Yet the day before the strikes, 150 users had placed bets that a war would break out within 24 hours. Investigations found that a single account, “Magamyman,” collected over $553,000 from bets tied to Iran and Khamenei immediately before the assault. Unlike the month-long Khamenei wager, these expired within a day, guaranteeing immediate loss or gain. At that scale, the wagers appeared to rely on information rather than intuition.
It was not the first time. Months earlier, a bettor won $400,000 by predicting that Venezuelan President Nicolás Maduro would vanish from the heart of Venezuela on the very day he was abducted in a covert American operation, not publicly announced until after it was carried out. The bettor, it subsequently emerged, was a soldier who had taken part in the operation and was privy to its classified details. He had not predicted the future. He had known it.
Trading in predictions
Online betting platforms have seen enormous uptake among Americans, particularly during Trump’s second term, with users wagering on everything from sporting events and entertainment to the insults Trump might direct at his political opponents.
Polymarket, the most prominent such platform in the United States, operates on the concept of “prediction markets,” converting future events into financial instruments that can be traded among bettors. Users buy “Yes” or “No” shares on a given event at prices ranging between one cent and one dollar, depending on the perceived probability of that event occurring.
What remains opaque is not the movement of the money but the identity of the wallet holder
In January 2022, the US Commodity Futures Trading Commission fined Polymarket $1.4 million for operating an unregistered derivatives and binary options trading platform. Under a legal settlement, it was forced to block all users within the United States, pushing American users toward virtual private networks (VPNs) to access the site and continue betting.
To guarantee value stability, these platforms rely on cryptocurrencies and stablecoins such as USDC, which is pegged to the dollar. Transactions are recorded on a blockchain network such as Polygon, which is public and whose financial flows are visible to anyone. What remains opaque is not the movement of the money but the identity of the person or entity controlling the wallet.
Trump: The Gambling Man
The “Venezuela prophecy” affair ignited particularly fierce controversy within American circles. It prompted Trump to declare his hatred of prediction and betting markets, according to a New York Times report, which added that the White House had warned its staff against wagering on government decisions.
Yet this purported hatred lacks expression in reality. Trump and his family have been involved in betting and prediction markets since the 1990s, when he resorted to sports betting as a “lifeline” after his Atlantic City casinos ran aground.
Trump Jr. serves as a financial adviser to the two largest companies on which most of the bets were placed
Trump Media & Technology Group, the largest single source of Trump’s wealth since its IPO in 2024, also announced plans to launch its own cryptocurrency-based prediction betting platform, under the name “Truth Predict.”
Notably, Donald Trump Jr., the president’s eldest son, serves as financial adviser to the two biggest betting platforms, Kalshi and Polymarket, and holds major investment stakes in both.
At a congressional hearing, Democratic Representative Jim McGovern put a question to CFTC Chairman Mike Selig about the Trump family’s involvement, to which Selig replied that “the Commission does not tolerate market manipulation.” When asked about Trump Jr.’s financial interests — interests members of Congress say prevent them from restricting this activity — Selig declined to answer.
In response to questions about Trump Jr.’s relationship with the prediction markets, his spokesman Andrew Surabian told CNN that he “does not trade on prediction platforms, and that his role with Kalshi and Polymarket is limited to advising on marketing strategies.”
Beyond the bets
It is not only bettors who are profiting from information trading. Many others have reaped substantial gains through stock market speculation. US Defense Secretary Pete Hegseth is chief among them: weeks before the war on Iran began, he attempted to make a major investment in an American defense fund through his financial broker at Morgan Stanley.
Ultimately, that deal was not completed. However, his efforts laid bare the impulse among officials to convert exclusive, classified information into monetary gain. It’s Hegseth’s actions that led Democratic Senator Chris Murphy of Connecticut to accuse “those around Trump of profiteering from war and death.”
After Trump threatened to destroy Iran’s power stations, oil infrastructure, and critical facilities in late March, markets braced accordingly — stocks fell and oil rose. Then followed a move no one had anticipated: at 7:05 am on March 23, Trump posted on Truth Social about a five-day grace period, alluding to negotiations with the Iranian side.
Yet in the 15 minutes before Trump’s post went live, Senator Murphy noticed simultaneous buy-and-sell activity: one or more individuals purchased $1.5 billion worth of S&P 500 index shares. The pattern repeated itself across several international markets, including Germany’s DAX and the European Euro Stoxx 50.
In that same 15-minute window, futures contracts on Brent crude worth $580 million were sold; 6,200 contracts in five minutes, against a typical daily volume of roughly 700 contracts. The market had no framework for what it was seeing.
War profits
This pattern of insider trading repeated again on Friday, April 17. Just before Iranian Foreign Minister Abbas Araghchi announced that the Strait of Hormuz had been reopened, Reuters reported that a total of 7,990 Brent crude contracts, worth approximately $760 million, were sold.
But the most contentious revelation came on May 14, 2026, when the US Office of Government Ethics published a 113-page document establishing that an account in Trump’s name had executed 3,642 trades during the first three months of 2026, with a volume ranging between $220 million and $750 million — an average of 60 trades per day.
Most strikingly, on the same day Trump declared a de-escalation with Iran and oil prices collapsed by 11%, the account was buying shares in oil companies such as ExxonMobil and Chevron, as well as defense contractors like Lockheed Martin and General Dynamics — companies that profit from war, not peace. In other words, Trump was telling his people “the war is nearly over,” while placing his own money on precisely the opposite, betting that the war would drag on.
The real question, then, is not where the information came from. It is whether the decisions of war and peace are being made, at least in part, to serve a portfolio.
It won’t happen again
“The underlying problem is not insider trading, it’s public corruption,” argues American economist Adam Michel, a researcher at the Libertarian Cato Institute. “It’s the fact that the government has inserted itself so deeply into so many different markets and has so much influence on market outcomes.”
Trump has pardoned more than 70 people, most facing fraud or tax-evasion charges, nearly all of them donors or allies who backed his path to office. By mid-2025, his administration had dropped cases against 166 companies, 30 of which had donated directly to Trump or his campaign.
To neutralize legal bodies that could pose a threat to his inner circle and allies, Trump slashed the number of lawyers and legal staff working in the Department of Justice’s Public Integrity Section — a division established in the wake of the Watergate scandal under President Nixon — from 36 members to just two, preventing any new cases from being pursued.
As for the Securities and Exchange Commission (SEC), which is nominally tasked with overseeing the integrity of commercial and financial practices, its chair resigned this year after being barred from pursuing any cases involving Trump’s family or his inner circle. In her place, a new division for combating fraud and financial crimes was established under the chairmanship of Vice President JD Vance, and designed to operate exclusively against Democrats.
Even the CFTC, whose chairman Mike Selig was asked to investigate the suspicious activity in the betting markets, is suffering from severe staff and funding shortages. Trump has declined to appoint new members to its board, leaving its current chairman alone on a commission that is supposed to have five members.
And so illicit profiteering, in the stock and betting markets alike, moves in a recurring pattern: a single source holds information the majority cannot access, while no investigative body exists to expose these violations and hold those responsible to account. For all this, the credit goes to President Donald Trump.