At 6:50 a.m. Eastern on Monday, trading volume in S&P 500 futures and West Texas Intermediate crude suddenly spiked. The premarket session had been quiet. Then, in a matter of minutes, someone placed large bets on stocks rising and oil falling.

Fifteen minutes later, President Donald Trump posted on Truth Social that the U.S. and Iran had held talks and that he was halting planned strikes on Iranian energy infrastructure. S&P futures jumped 2.5%. Crude dropped nearly 6%.

Whoever traded at 6:50 a.m. made a fortune.

The timing was either extraordinarily lucky or something else entirely. And it wasn’t an isolated incident.

The Pattern

On Polymarket, the blockchain-based prediction platform, a single trader has won nearly $1 million since 2024 betting on U.S. and Israeli military actions against Iran. According to an analysis by Bubblemaps, a blockchain analytics firm, this anonymous bettor won 93% of their wagers exceeding $10,000 — all on unannounced military operations.

The pattern is striking. Hours before Israeli strikes on Iran in October 2024. Hours before U.S. airstrikes on Iranian nuclear facilities in June 2025. Hours before the joint U.S.-Israeli operation that launched the current war in February.

“All of this is strong signaling of insider activity,” Bubblemaps CEO Nick Vaiman told CNN. “This is pretty suspicious in my book.”

Over the weekend, eight newly created Polymarket accounts bet nearly $70,000 on a U.S.-Iran ceasefire before March 31. They stand to collect $820,000 if the deal materializes. The accounts were created around March 21 — the same timeframe when Trump’s rhetoric shifted from escalation to “winding down.”

Ben Yorke, a cryptocurrency researcher, said the wallet activity suggests either a large investor masking their position or outright insider trading. “When you see wallet-splitting and deliberate attempts to obfuscate identity,” he told The Guardian, “it’s one of two scenarios.”

The Rules Catch-Up

On Monday, both Polymarket and Kalshi — its regulated competitor — announced new insider trading rules.

Polymarket banned trades based on confidential information, trades based on illegal tips, and participation by anyone in “a position of authority or influence” over an event’s outcome. Kalshi rolled out what it calls “primitive political screening” — technological guardrails to preemptively block politicians and athletes from betting on their own events.

“These rule enhancements make our expectations abundantly clear,” said Polymarket chief legal officer Neal Kumar.

The timing was not coincidental. Prediction platforms face their most intense scrutiny yet as lawmakers demand accountability and state regulators pursue legal action. Nevada issued a temporary suspension order against Kalshi this month. Arizona filed criminal charges.

The Enforcement Gap

The problem with Polymarket’s new rules is enforcement. The platform operates internationally outside U.S. regulatory reach, and Americans can easily access it via VPN. Accounts are anonymous. Blockchain transactions can be traced, but wallets cannot be publicly linked to individuals.

Israel has already indicted two people, including a military reservist, for allegedly using classified material to bet on Polymarket during the war. The U.S. has not announced similar prosecutions.

The Commodity Futures Trading Commission issued guidance reminding operators that insider trading is illegal and that the agency can investigate violations. But guidance is not enforcement, and the CFTC’s current leadership — appointed by Trump — has been friendly toward prediction markets.

Todd Phillips, a Georgia State University finance professor and former CFTC advisory board member, said the 93% win rate defies explanation. “Having win rates in the 80% to 90% range is just too good to be true,” he said. “I look at this, and I think something fishy is going on.”

What the Markets Know

Prediction markets were supposed to aggregate dispersed information — to surface truth through price discovery. Polymarket’s CEO, Shayne Coplan, told Axios last year it was “super cool” that his platform “creates this financial incentive for people to go and divulge the information to the market.”

But when that information comes from classified military planning, the market becomes something else: a mechanism for monetizing secrets, potentially distorting decisions about war and peace.

The suspicious trades this week — in both traditional futures and prediction markets — raise a question that no rule change can fully address. When traders consistently profit from events they shouldn’t know about, and regulators lack the tools or will to stop them, what exactly are these markets predicting?

Or are they simply paying off the people who already know?

Sources