Millions Are Being Wagered by People Who Seem to Know Exactly What Trump Will Post Next
Although there can certainly be no doubt that the United States has descended in the last few years into a full-on national gambling addiction that is only now beginning to result in criminal charges to rein in the the likes of prediction markets, in a wider sense, it seems equally likely that much of the money being placed into the stock market or prediction markets is hardly a “gamble” at all. By which we mean: It’s being wagered on those markets by people who already know what the market is about to do, because they’re privy to information that the rest of us aren’t allowed to have. And because the market can be so easily and so quickly manipulated by something as small as a non-fact-checked social media post from our capricious President, this has resulted in opportunities for a clandestine few to make a whole lot of money by seemingly knowing what the likes of Donald Trump will do or say, before he does it.
There have been numerous instances of this type of scenario playing out over the course of the second Trump administration, but this week brought perhaps the biggest money-maker to date, in terms of the sheer amounts of cash that were wagered on the probability of an outcome Trump personally delivered only minutes later. At roughly 6:50 a.m. EST on Monday, Financial Times reports that more than $580 million trades on oil futures were placed, despite no obvious reason for such high volumes. Just 14 minutes later, however, Donald Trump graced Truth Social with one of his all-caps proclamations, claiming that the U.S. had been engaged in “productive” peace talks with Iran, in a seeming effort to soothe the surging price of oil despite Iran saying that Trump is full of shit and that talks weren’t happening. The post had its intended, market-manipulating effect, as oil prices rapidly declined, and the value of a barrel of Brent Crude fell from a high near $114 to less than $100. And the people who profited most were those who bet on the declining price of oil just 14 minutes earlier. Said one market strategist quoted by Financial Times: “It’s hard to prove causality … but you have to wonder who would have been relatively aggressive at selling future at that point, 15 minutes before Trump’s post.”
The publication was also able to actually wrangle a press statement out of the administration on this specific, suspicious piece of trading, with White House spokesperson Kush Desai rebuffing the implied accusation: “The White House does not tolerate any administration official illegally profiteering off of insider knowledge, and any implication that officials are engaged in such activity without evidence is baseless and irresponsible reporting.”
But the actual traders working in the industry aren’t buying those denials. Another portfolio manager quoted by Financial Times summed up what he called a “level of frustration” among institutional investors who increasingly suspect those with inside information of the administration of shameless profiteering. Or as he put it: “My gut from watching markets for the last 25 years is this is really abnormal. It’s Monday morning, there’s no important data today, there aren’t any Fed speakers you’d want to front run. It’s an unusually large trade for a day with no event risk . . . Somebody just got a lot richer.”
BREAKING: Just five minutes before Trump's announcement to halt the attacks on Iran, massive trades hit the market.
$1.5 billion in S&P 500 (ES) futures was bought while $192 million in oil (CL) futures was sold.
These orders were 4–6x larger than anything else.
They made huge gains.
Unusual.
— Unusual Whales (@unusualwhales.bsky.social) Mar 23, 2026 at 2:17 PM
For the second Trump administration, however, these types of headlines have simply become par for the course. It’s not as if the President and his family have made any effort whatsoever to look as if they’re uninvolved in the prediction market industry in particular–instead, both Trump and his eldest son have gotten deeply financially intertwined with them. The President’s own Trump Media and Technology Group has announced plans as of last fall for its own prediction-based cryptocurrency platform called Truth Predict, which would be an obvious gold mine for graft for anyone with insider information. Donald Trump Jr., meanwhile, is a paid adviser for Kalshi and on the advisory board of Polymarket simultaneously. You know, the sort of conflicting financial entanglements that would never have been socially permitted for Presidents or their highly visible family members in any administration before the mid-2010s.
So much of this is predicated on an ability Trump has clearly come to realize he possesses, which is the ability to shove the market one way or the other via a single announcement or social media post–not necessarily for any extended period, but long enough to make vast sums for people betting on a surge in either direction. He has at times even let retail investors in on the chaotic fun, as he did back in April of 2025 when posting “THIS IS A GREAT TIME TO BUY!!!” on Truth Social just hours before he would announce a 90-day pause on all of his “liberation day” tariffs, causing markets to sharply rebound. This example is an exception, however–typically, the only ones doing any profiting are anonymous traders who arrive to place massive wagers only minutes before Trump posts or the government announces it is taking a large and consequential action.
Stop worrying about how much insider trading is going on.
Worry about how much policy is being formed for the express purpose of enriching the president’s cronies through insider trading.
— StrictlyChristo ???????????????????? (@strictlychristo.bsky.social) Mar 23, 2026 at 2:36 PM
Prediction markets have been particularly valuable to anonymous traders for this purpose, as highlighted by two key instances in 2026 in which bets were placed on Polymarket only hours or minutes before the U.S. military began major operations. In January of this year, an unknown trader made $400,000 betting on the ouster and extraction of Venezuela leader Nicolas Maduro, doubling the amount wagered on their position on Polymarket just hours before U.S. aircraft began a stealthy raid and extraction operation that resulted in Maduro’s capture. And just last month, six anonymous accounts combined to make roughly $1.2 million in profit by betting on the precise timing of U.S. strikes on Tehran in the opening moments of the ongoing Iran War. Once again in this case, the bets were placed only a few hours before the U.S. offensive kicked off. In fact, nearly everything Trump does on a daily basis could conceivably make someone richer via prediction markets like Kalshi and Polymarket, given that they maintain things like “mention markets,” in which users can bet on whether Trump will say specific words during a speech. The opportunity for insider trading and graft in such a market should be patently obvious.
Even those prediction markets seem to realize that graft on this level is entirely too visible, and that they’ll be risking damaging regulation if they don’t at least give a greater appearance of attempting to combat accusations of insider trading. Just yesterday, both Kalshi and Polymarket announced that they would be introducing “new industry guardrails and new surveillance tools,” according to the Associated Press, after two U.S. Senators (Sen. Adam Schiff D-CA and Sen. John Curtis R-UT) introduced broad bipartisan regulatory legislation called the “Prediction Markets are Gambling Act,” striking the same tone as the state of Arizona’s criminal case against Kalshi. Kalshi said its new rules to combat insider trading would ban political candidates from trading on their campaigns, and block people involved in college/professional sports from trading on their sport, while Polymarket insisted its new rules now “say clearly that users cannot trade on contracts where they might possess confidential information or could influence the outcome of an event.” Not mentioned: How the prediction markets would actually determine or enforce any of this.
As the SEC's enforcement director, Margaret Ryan pushed to aggressively pursue charges against Justin Sun (a major backer of the Trumps' World Liberty Financial crypto venture) & Elon Musk.
Instead, the SEC settled with Sun & is in talks to settle with Musk.
Ryan resigned in frustration last week.
— Ken Vogel (@kenvogel.bsky.social) Mar 24, 2026 at 10:33 AM
One thing we obviously can’t rely upon is the idea that Trump’s own federal government will crack down on any form of enrichment available to the cronies in his orbit. It would, after all, be the job of the Securities and Exchange Commission to investigate and tackle reports of insider trading and illegal activity in financial markets, but wait, what’s that–the SEC’s top enforcement official resigned last week after “reportedly clashing with the regulatory body’s leadership over the handling of cases linked to President Donald Trump”? Does that seem like the sort of thing that might happen in an administration where corruption is out of control?
No one is coming to right these types of wrongs–the people in charge of doing so have already quit or been forced out. Is there some way we can profit by betting on just how much more visible this corruption can become?