Who Profits From the Iran War: Inside the Trades That Cashed In Early

On Monday, the 23rd of March, the world held its collective breath. Everyone was waiting for the United States to deliver on an ultimatum. Donald Trump had given Iran forty-eight hours to reopen the Strait of Hormuz, and if that did not happen, he had promised to obliterate Iranian power plants. Iran, for its part, had said that if the strikes came, it would target energy and desalination infrastructure across the region.

That would have been the single greatest escalation in the war so far. Had it happened, the Middle East would look even worse than it does now. Fuel prices, already elevated, would have spiked further, and stock markets would have crashed soon after. In fact, Asian markets had already fallen sharply in anticipation of what was coming. South Korea’s benchmark KOSPI plunged 6.5 percent, Japan’s benchmark Nikkei 225 fell 3.5 percent, and Hong Kong’s Hang Seng Index tumbled more than 4 percent.

The worst-case scenario did not arrive. On that Monday, President Trump announced that Tehran and Washington were having very good and productive conversations on the resolution of hostilities in the Middle East. As a result, he instructed the Department of Defense to postpone military strikes against Iranian energy infrastructure for five days, and suggested a deal to reopen the Strait could even be coming soon. The world exhaled, oil prices dropped by more than 10 percent in some cases, and stock markets surged.

By itself, none of this is out of the ordinary; during a war, threats get made, negotiations happen, and plans change. What was out of the ordinary, and has become a major concern for US prosecutors, is the number of people who seemed to know in advance that the president would walk back his ultimatum — and just how much money they made as a result.

The Minute the Markets Moved

The clearest signal that something unusual was happening came in the financial markets, in the span of a single minute. According to the Financial Post, traders placed millions of dollars’ worth of bets in the oil market right before Donald Trump’s post sent the price of crude tumbling.

Between 6:49 and 6:50 a.m. Eastern Standard Time, roughly 6,200 Brent and West Texas Intermediate futures contracts changed hands, with the Financial Times estimating that the trades were worth $580 million. According to Unusual Whales, a financial data platform that provides market-transparency tools for retail investors, $1.5 billion in S&P 500 futures were purchased in one fell swoop, while $192 million in oil futures were sold.

These orders were four to six times larger than anything else happening at the time, and Unusual Whales believed the trader made huge gains. Spikes appeared on other futures markets too — the DAX Index Futures, the Euro Stoxx 50 Index, and across the Nasdaq and Russell 2000 indexes, according to Bloomberg.

To most observers, this kind of activity was highly unusual. It happened before the market opened on a Monday, on a day without an anticipated news hook — no release of critical US economic data, no company earnings call. The trades were perfectly positioned, and perfectly timed, for a price move that had not yet been announced.

The Polymarket Bets

These moves were not limited to the stock market. On Polymarket, a predictive betting website where people can wager on real-world events, users have been making a large number of bets that analysts consider suspicious at best, or at worst a clear example of insider trading.

According to the Guardian, eight newly created accounts placed bets worth a combined $70,000 on whether a ceasefire would be declared before the end of March. The outlet reported that all eight accounts appear to have been created around the time when President Trump first appeared to double down on war with Iran, but then suggested, in a Truth Social post made after the markets were closed, that he was considering winding down military operations. Following that activity, Polymarket’s own odds on a ceasefire before March 31 jumped sharply, from 6 percent on March 21 to 24 percent by Monday. If a ceasefire had been reached, the accounts responsible for the shift stood to make $820,000.

Ben Yorke, formerly a researcher at the media outlet CoinTelegraph, told the Guardian that the wallets looked like someone with some degree of inside information. There is a complication worth naming: the 31st of March passed without a ceasefire, and that trader lost money on the bet, which might indicate the account was not an insider after all. However, given the timing, it is possible the bet reflected a belief within the Trump administration, or among people close to it, about when a ceasefire could be reached.

The Strikes That Started the War

The March ceasefire bets were not even the most dramatic examples of potential insider trading on Polymarket. Those came a full month earlier, on the night before the February 28th strikes that began the war itself.

An independent on-chain analyst known as Andrew 10 GWEI told Al Jazeera he had discovered 38 accounts that had won more than $2 million betting correctly on the strikes. Each of the accounts, which Andrew believes are controlled by one person, placed between four and ten bets with a nearly 100 percent success rate. Notably, the user began preparing accounts with cryptocurrency transfers on the 22nd of February, before bets were placed on the 27th. Another user, named MagaMyMan, made $515,000 from an $87,000 bet around the same time.

They were not the only winners. The New York Times found at least 16 accounts that placed bets on the 27th, with each account making over $100,000. There were also 109 accounts that made over $10,000. To be fair, not every person who won on Polymarket did so using inside information. Platforms like Polymarket are built on informed speculation, and some traders are simply better at reading geopolitical signals than others. Many rely on open-source intelligence rather than foreknowledge of attacks.

How Analysts Spot a Suspicious Wallet

In this case, though, there is good reason to be suspicious, according to analysts who study these platforms and have developed a shortlist of warning signs to identify possible insider trading.

Researchers look for practices like wallet-splitting — dividing bets among a series of accounts to avoid detection — or opening multiple wallets to place a new bet. New wallets, with no history, placing large bets, are a massive red flag. As Ben Yorke put it to Al Jazeera: “The most important aspect of a suspicious wallet would be a wallet with no history before. An average user of Polymarket will have a long history, but if you’re doing insider trading, you wouldn’t want that link, so you would create a fresh wallet.”

The X account Polymarket History recently identified several newly created accounts that fit the bill. These accounts had bet $2 million on the same three predictions: no ceasefire by the 31st of March, no entry of US forces into Iran by the 31st, and US forces to enter Iran by the 30th of April. As of early June 2026, two of those predictions have come true, and if the third also comes true — which looks likely, with the Washington Post reporting the Pentagon is preparing for weeks of a ground invasion — those accounts will walk away with millions.

Who Stands to Gain

That leads to the most important question: who stands to gain? At the moment, the honest answer is that we simply do not know. Tracking down the person behind a specific Polymarket wallet is genuinely difficult.

The platform does not require users to submit identification, and most American traders access it through VPNs that mask their location and identity. Crypto-analytics firms can track on-chain movements and flag suspicious patterns, but connecting a wallet address to a real person remains a significant challenge. Another reason this is extremely hard is that Polymarket runs an offshore division for its most controversial markets — including those on Iran — unencumbered by US federal regulations.

By contrast, it is a lot harder to hide in the traditional stock market, because trades leave a traceable paper trail. And that paper trail has produced one of the most serious accusations of insider trading. According to the Financial Times, a broker for Defense Secretary Pete Hegseth attempted to invest in major defense companies in the weeks before the war in Iran began.

The Times reported that Hegseth’s broker at Morgan Stanley contacted BlackRock in February about making a multimillion-dollar investment in the asset manager’s Defense Industrials Active ETF. The investment did not ultimately go ahead, because the fund was not yet available for Morgan Stanley clients to buy at the time.

It is important to note that a Pentagon spokesperson called the report entirely false and fabricated, and demanded that it be retracted. The Financial Times, however, is standing by its reporting. Whether or not the trade went through, defense stocks surged in the weeks after the war began. Someone positioned correctly, ahead of February 28th, would have made a significant return.

A Conflict at the Top

There is another name worth raising: Donald Trump Jr., who serves as an adviser to Polymarket and its competitor Kalshi. His venture capital firm, 1789 Capital, has also invested an undisclosed amount in Polymarket.

A spokesperson for Trump Jr. told CNN that the president’s son does not trade on prediction markets, and that he only advises Kalshi and Polymarket on marketing strategies. However, the position gives the president’s son a financial stake in a platform that has generated hundreds of millions of dollars in war-related bets, at a time when his father’s administration controls the very decisions those bets are wagered on. At best, this is a conflict of interest, and at worst it looks like the latest example in what the New Yorker described as the corruption endemic to the Trump administration.

According to the Brennan Center for Justice, since taking office in January 2025, President Trump has pocketed an estimated three billion dollars from his various business enterprises. His family is estimated to have raked in billions more. Much of the money appears to be coming from foreign governments and others seeking to curry favor with the Trump White House.

The clearest example is when Sheikh Tahnoon bin Zayed Al Nahyan, the UAE’s national security adviser, purchased a 49 percent stake in World Liberty Financial, the Trump family’s main cryptocurrency platform, for 500 million dollars. Months after the deal was signed, the US agreed to give the UAE access to 500,000 of America’s most advanced AI chips per year, with a fifth of those chips going to Tahnoon’s own AI company, G42. Before Trump’s second term, the Commerce Department had imposed strict export controls on precisely those chips, to prevent advanced semiconductors from reaching China via Middle Eastern intermediaries — and government officials had identified G42 as a security risk.

The National Security Question

That deal, the suspicious stock market activity, and the dozens of Polymarket trades all raise the same uncomfortable question: if insiders are trading on what they know, then are they telling the world what they know?

Consider what happened on the 3rd of January. US special operations forces launched Operation Absolute Resolve, a raid on Caracas that captured Venezuelan President Nicolás Maduro and his wife, Cilia Flores, from their fortified compound. It was one of the most complex operations in recent history, involving more than 150 military aircraft and 200 special operators. General Dan Caine, the chairman of the Joint Chiefs of Staff, said the entire mission lasted about two and a half hours, with only 30 minutes spent on the ground.

Most importantly, there were no American fatalities.

The success of that mission depended on one thing: secrecy. Top members of Congress were not informed ahead of time, and while some news outlets knew about the raid in advance, they held off on reporting it, to avoid tipping off Maduro and putting American lives at risk. Traders on Polymarket made no such consideration. According to the Wall Street Journal, a newly created account placed roughly $32,500 in bets on Maduro being removed from power before January 31.

The trader made more than $400,000 once President Trump announced Maduro’s capture. Fortune reported that the account, created less than a week before the capture, only made bets associated with Maduro’s exit and the US going to war with Venezuela.

Real-Time Intelligence for Adversaries

As Slate pointed out, the only thing Maduro or someone in his inner circle needed to do to get a decent idea of the imminent American raid was to pull up a specific betting market on Polymarket. A similar scenario played out in the hours before the strike on Iran.

According to Bubblemaps, a blockchain analytics firm, six accounts, all created in February, made roughly $1.2 million in profit by correctly betting that the US would strike Iran on the 28th. Most of these wallets were funded within 24 hours before the attack, and had only ever placed bets on when US strikes might occur. Some of their bets were placed just hours before the first explosions were reported in Tehran.

This matters because, just days before the strikes, American and Iranian officials had been in Geneva for a third round of Omani-mediated nuclear talks. The talks were going so well that Iran’s foreign minister, Abbas Araghchi, publicly said a deal was within reach. And it was not just Iran that thought a peace deal was possible — Oman’s foreign minister, Badr Al Busaidi, said the same thing in an interview with CBS. If the Iranians had checked Polymarket, they would have known that a deal was not likely, and they might have launched their own preemptive strikes.

This is the risk that analysts have been flagging since January. Prediction markets can become real-time intelligence indicators for adversaries, which, according to Matt Motta, a professor at Boston University’s School of Public Health, puts military personnel in more danger than is operationally necessary. The risk is so great that Daniel O’Boyle, a senior analyst at InGame Intel, has argued that if Russia had designed a system to degrade US operational security while generating anti-American narrative material, it would look a lot like what Polymarket already does.

O’Boyle also pointed out that hostile actors could use the platform to sow panic — for instance, by placing large wagers on something like a nuclear detonation, because those wagers would seem to come from someone with inside knowledge. This kind of manipulation would not require sophisticated tradecraft. Because of the anonymity provided to users, anyone with enough capital can move prices and influence the public without revealing their identity or intentions.

Why Isn’t Anyone Stopping It?

Which leads to the final question: if insider trading and prediction markets pose such a huge risk to national security, then why isn’t anyone doing anything about them?

The truth is, the framework to address this already exists. Insider trading is already illegal, and the regulatory agency with primary responsibility for enforcing US laws in futures markets is the Commodity Futures Trading Commission, or CFTC. The CFTC has identified insider trading in prediction markets as one of its five core enforcement priorities, and enforcement director David Miller has warned that the agency is actively monitoring suspicious activity.

Speaking at New York University, he said: “There is a myth in the mainstream media and social media that insider trading law doesn’t apply in the prediction markets. That is wrong.”

The issue is that, despite Miller’s statement, enforcement has been inconsistent. NPR found that under President Trump in 2019, the Securities and Exchange Commission brought just 32 insider trading enforcement actions, the lowest number since 1996. The numbers were equally low in 2025.

According to Reuters, in 2025 the CFTC’s Division of Enforcement brought just 11 enforcement actions and obtained less than a billion dollars in monetary relief, less than $10 million of which resulted from actions filed by the current administration. By comparison, in 2024, during the Biden administration, the agency brought 58 enforcement actions and obtained monetary relief of over $17.1 billion. Critics argue that this decline in enforcement across financial markets signals a permissive environment for misconduct.

The Legislative and Industry Response

This has drawn the ire of several lawmakers. Connecticut Senator Chris Murphy and Texas Representative Greg Casar recently introduced the Banning Event Trading on Sensitive Operations and Federal Functions Act — and, yes, that acronym is BETS OFF. It is a bicameral piece of legislation to ban wagering on government actions, terrorism, war, assassination, and events where an individual knows or controls the outcome. Because many of these event contracts are traded on offshore platforms like Polymarket’s non-US site, the bill would amend existing laws against illegal gambling to cut off payment systems to these platforms, and impose criminal penalties on anyone in the United States who runs or promotes them.

Because of this increased scrutiny, prediction-market platforms have been proactively implementing new regulations and surveillance tools, to try and forestall government oversight. Kalshi said it would ban political candidates from trading on their own campaigns, and would preemptively block anyone involved in college or professional sports from trading contracts related to the sports they play or are employed by. Polymarket rewrote its rules to say clearly that users cannot trade on contracts where they might possess confidential information or could influence the outcome of an event.

That would include athletes, company officials, policymakers, or anyone who would have enough influence to affect the outcome of an event or know the information in advance. These measures can work with accounts linked to known public figures. But given that accounts on these sites are often anonymous and accessible through VPNs, enforcement against bad actors remains a significant challenge.

The Revolving Door

Polymarket has gone further in its attempt to win over regulators, holding a three-day pop-up event called the Situation Room, in the heart of Washington, D.C.’s lobbying district. Neil Kumar, the company’s chief legal officer, called the event a coming-out party.

It is worth pointing out that, before Kumar joined Polymarket, he worked for the CFTC, in the office of the General Counsel. This is part of an issue that observers have long warned about. When public sector employees end up working for the private firms that they monitored, regulated, and even disciplined, a clear conflict of interest arises. A regulator who has one eye on a future private-sector job is unlikely to be the industry’s harshest critic.

But regulators might catch up eventually. Federal prosecutors in Manhattan are now exploring whether certain lucrative bets placed on prediction markets have violated insider trading and other laws. Officials from the Southern District of New York’s fraud unit recently met with representatives of Polymarket to discuss how existing laws could be applied to potential misconduct in the fast-growing industry. The meeting happened after Jay Clayton, the US Attorney for the district, said that he believed there would be criminal cases involving prediction-market activity.

Why Prosecution Is Hard

Still, prosecution may prove challenging. Aitan Goelman, a criminal defense lawyer who previously served as the director of enforcement at the CFTC, told CNN that criminally prosecuting someone would be difficult if the law was vague.

Prosecutors would have to show that someone was not only trading while in possession of material nonpublic information, but that they were also doing it in violation of some kind of fiduciary duty, or duty of trust. Additionally, prosecutors will have a hard time with trades that took place on marketplaces outside of the US.

Despite these challenges, US regulators tend to agree: these bets have to be reined in somehow. Because if they are not, it will not only normalize corruption, and the monetization of government secrets, but it will also make American operations more vulnerable for years to come. The stakes are not abstract. Every anonymous wallet that cashes in early on a strike, a raid, or a ceasefire is a small leak in a system that depends on secrecy — and a quiet incentive for the next leak to be larger.

Frequently Asked Questions

What happened in the financial markets just before Trump’s March 23rd announcement?

In the single minute between 6:49 and 6:50 a.m. Eastern Standard Time, roughly 6,200 Brent and West Texas Intermediate oil futures contracts changed hands — trades the Financial Times estimated at $580 million. Unusual Whales reported $1.5 billion in S&P 500 futures bought and $192 million in oil futures sold, in orders four to six times larger than anything else at the time. The activity happened before the market opened, on a day with no anticipated news hook.

What is Polymarket, and why are its bets controversial?

Polymarket is a predictive betting website where users wager on real-world events, such as whether a ceasefire will be declared by a certain date. Its bets became controversial because clusters of newly created, anonymous accounts repeatedly placed large, correct wagers on Iran-war outcomes — including the February 28th strikes — winning millions. Analysts consider this suspicious at best and, at worst, a clear example of insider trading.

How do analysts identify likely insider trading on these platforms?

Researchers look for practices like wallet-splitting, dividing bets across many accounts to avoid detection, and opening multiple fresh wallets to place a single bet. The single biggest red flag is a brand-new wallet with no prior history suddenly placing large bets. As one analyst explained, an ordinary user has a long trading history, but someone trading on inside information would create a fresh wallet to avoid that link.

What is the accusation involving Defense Secretary Pete Hegseth?

The Financial Times reported that a broker for Hegseth attempted to invest in major defense companies in the weeks before the Iran war began, contacting BlackRock in February about a multimillion-dollar investment in its Defense Industrials Active ETF. The investment did not proceed because the fund was not yet available to Morgan Stanley clients. A Pentagon spokesperson called the report entirely false and fabricated and demanded a retraction; the Financial Times stands by its reporting.

How are prediction markets a national security risk?

Because the markets aggregate bets in public, their odds can act as real-time intelligence indicators for adversaries. Slate noted that Maduro’s circle could have anticipated the US raid simply by checking a Polymarket page, and a sudden shift in Iran-strike odds could have signaled to Tehran that the Geneva nuclear talks were collapsing. Analysts warn this can put military personnel in more danger than is operationally necessary and could even be exploited to sow panic.

Is insider trading on prediction markets actually illegal?

Yes. Insider trading is already illegal, and the CFTC, which regulates futures markets, has named it one of its five core enforcement priorities. Enforcement director David Miller has stated plainly that the myth insider-trading law does not apply to prediction markets is wrong. The harder problems are inconsistent enforcement, anonymous VPN-masked accounts, offshore platforms beyond US jurisdiction, and the legal burden of proving a breach of fiduciary duty.

What is being done to rein these markets in?

Senator Chris Murphy and Representative Greg Casar introduced the BETS OFF Act, which would ban wagering on government actions, war, terrorism, and assassination, cut off payments to offshore platforms, and impose criminal penalties on US operators. Platforms have added their own surveillance rules, Manhattan federal prosecutors are exploring possible insider-trading cases, and the US Attorney for the Southern District of New York has said he expects criminal cases involving prediction-market activity.

Sources

• Trump issues 48-hour Hormuz Strait ultimatum, threatens Iran power plants — Al Jazeera
• Asian stock markets plunge amid Trump’s ultimatum on Iran — Al Jazeera
• Oil prices, Trump, Iran, Strait of Hormuz — CNBC
• Traders, oil bets, and Donald Trump’s social media before Iran talks — Financial Post / Financial Times
• Polymarket user made $400k on Maduro capture bets amid insider-trading suspicion — Fortune
• Unusual Whales — futures activity thread
• Prediction markets and the Justice Department — CNN
• Bets on US-Iran ceasefire show signs of insider knowledge, say experts — The Guardian
• Archived report
• Insider trading, prediction markets, and Trump rules — NBC News
• Revolving doors and regulatory capture — CEPR / VoxEU