White House confronted over shady stock trades and bets ahead of key Trump announcement

Moments before President Donald Trump announced that talks with Iran were going well and that he would not make good on his threat to bomb one of their civilian power plants, someone dropped about $580 million in the oil futures market.

"In one move, $1.5 billion in S&P 500 futures were purchased. This trade was so large it sent the entire index +0.3 percent higher that minute," the independent news site Europa posted on X. "$192 million in oil futures were also sold."

It happened five minutes before Trump posted on Truth Social, saying he was de-escalating the situation in Iran.

Professor Adam Cochran pointed out that it was "more than 4x-6x any other trade size during the market close ... Insiders profited from his lies in broad daylight!"

The sell-off is also sparking further questions about huge bets on Polymarket, which allows people to bet on whether something will happen.

In January, a new user on Polymarket suddenly popped up with a huge investment, betting that Venezuelan President Nicolás Maduro would be ousted. It happened mere hours before he was taken by U.S. forces.

CNN reported on Tuesday that at least one person on Polymarket has made nearly $1 million since 2024 after a number of remarkably accurate and well-timed bets about military actions against Iran, an analyst shared.

"The bettor won a staggering 93 percent of their five-figure wagers about Iran, even though the events they predicted were unannounced military operations," the report said.

To put that in context, Todd Phillips, a finance professor at Georgia State University, told CNN that most high-frequency traders have a win rate closer to 50 percent.

"The Bubblemaps analysis showed that the Iran trader had an overall win rate of 83 percent, and a 93 percent rate for trades over $10,000. They netted nearly $967,000," CNN said.

“It sure seems like this person either has incredible luck, or was insider trading,” Phillips said. “Having win rates in the 80 percent to 90 percent range is just too good to be true. I look at this, and I think something fishy is going on.”

The better also won cash on a bet "hours before Israeli strikes in October 2024 during its tit-for-tat conflict with Iran, hours before US airstrikes against Iranian nuclear facilities in June 2025" and just hours before the surprise attack in February.

"There's some clear, potential signs of insider activity," reporter Marshall Cohen told Dana Bash on "Inside Politics" on Tuesday. "There could be an honest, reasonable explanation. We just don't know."

“All of this is strong signaling of insider activity, based on the amount they made, the markets they bet on, the timing of their trades, the success rates of these trades and the fact that they are connected on-chain,” Bubblemaps CEO Nick Vaiman told CNN about the trader. “This is pretty suspicious in my book.”

Kalshi, another site that allows betting like Polymarket, is in the U.S., so it must abide by U.S. insider trading laws. But Polymarket is headquartered overseas and doesn't have to abide by the same rules.

None of these prediction markets are regulated because they're so new and the law hasn't caught up with the technology yet.

On Monday, Polymarket announced new rules for offshore and US-based platforms, to “clarify three core categories of prohibited insider trading conduct.”

Essentially, the company's solution is to have users agree not to commit insider trading. They also put a page up on their website that explains what insider trading is.

"They banned trades based on information that users were legally required to keep confidential, and trades based on tips from someone with the same obligation," said CNN's report.

Polymarket said that people in “a position of authority or influence” over a major global event cannot bet on markets that are involved in those issues. The new regulations would mean that any inside information the families of those individuals also cannot be traded on.

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