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The People Betting on War Keep Winning. That's the Problem.

On prediction markets like Polymarket, you can wager real money on whether the U.S. is about to bomb someone. The unsettling part isn't that people do it. It's how rarely they lose.

The People Betting on War Keep Winning. That's the Problem.
Photo by Daniel Brzdęk on Unsplash

Here is the thing that should bother you, and it isn't the part you'd expect.

Yes, there is now a thriving online market where you can put money down on whether the United States is about to launch a military strike. On whether a foreign leader is about to be removed. On whether a war is about to end on a particular Tuesday. That's grim enough on its own — a casino floor built on top of other people's catastrophes. But that's not the alarming part. The alarming part, the part that turns your stomach a little once you sit with it, is how often the people placing those bets are right.

They keep winning. And in markets, when the longshots keep winning, it usually means someone at the table can see the cards.

Start with the case that put numbers on it. A small Paris-based analytics firm called Bubblemaps went looking through Polymarket and found nine connected accounts that had quietly pulled in more than $2.4 million betting almost exclusively on American military moves. Over more than eighty bets, these accounts hit a 98 percent win rate. Not on coin-flip questions either — on the specific timing of the first U.S. strikes against Iran, on the reported removal of Iran's supreme leader, on the announcement of a ceasefire. They called the shots on the exact days. And when they did lose, the losses were tiny, a few hundred dollars here and there, the kind of rounding error you'd expect from someone who already knows how the story ends and is just papering over the trail. "Luck alone cannot explain those numbers," Bubblemaps' Nicolas Vaiman told 60 Minutes, which is the kind of understatement that does a lot of work.

Then it gets worse, because it isn't nine accounts. It's a pattern.

Michelle Kendler-Kretsch and her team at the Anti-Corruption Data Collective went at it from a different angle. They pulled the longshots — bets over $2,500 placed when the odds of winning sat below 35 percent — and asked a simple question: how do these underdogs actually do? On sports, where nobody has a crystal ball, longshots like that win about 7 percent of the time, which is roughly what math says should happen. On military outcomes, the same kind of longshot wins 52 percent of the time. Fifty-two. That is not a market reading the future well. That is a market where a meaningful chunk of the players already know it. Kendler-Kretsch called it what it looks like — systemic insider trading — and added the line that lingers: it's "a culture around betting on war."

A culture. Not a glitch. Not a few bad actors. A culture.

Longshot win rate · bets placed under 35% odds
7%
Sports longshots — about what the math predicts
52%
U.S. military-action longshots
Separately, nine connected accounts hit a 98% win rate across 80+ bets on American military moves — pulling in $2.4 million.

Once you understand how a military operation actually comes together, the 52 percent stops being a mystery and starts being arithmetic. A strike, a raid, a capture — these things aren't decided by one person in a dark room. They move through a long chain of human beings: the officials who approve them, the planners who map them, the analysts who brief them, the logistics people who move the fuel and the aircraft. One of the digital detectives 60 Minutes spoke to — a man whose face and name they hid, because crypto sleuths have started getting violently kidnapped in what the industry casually calls "wrench attacks" — made the point plainly. Every one of those people is a potential insider. So, for that matter, is a spouse who overhears the wrong phone call. The information leaks out of the edges of the operation, and somewhere downstream, a number on a screen starts ticking in the right direction a few hours before the rest of us find out why.

If you want to know exactly what that looks like with a face attached to it, the government recently handed us one.

His name is Gannon Ken Van Dyke. Thirty-eight years old, an active-duty Army Special Forces master sergeant out of Fayetteville, North Carolina. Last December he was pulled into the planning of something called Operation Absolute Resolve — the U.S. mission to capture former Venezuelan president Nicolás Maduro and his wife. On the day he was read in, prosecutors say, he sat through a classified-information briefing and signed a nondisclosure agreement swearing he'd never reveal a word of it. He opened a Polymarket account about two weeks later.

Between late December and January 2, he loaded up on "Yes" — buying contracts that bet Maduro would be out by the end of January, hundreds of thousands of shares, at prices that reflected how unlikely the public thought it was. The public didn't know what he knew. In the predawn dark of January 3, U.S. forces raided Caracas and took Maduro. The bets resolved. Van Dyke walked away with roughly $409,000, and on the very day of the operation he started pulling his winnings out. When reporters and people online began noticing the suspiciously perfect Maduro trades, he allegedly tried to make himself disappear — asking Polymarket to delete his account by claiming he'd lost access to his own email, swapping the email on his crypto wallet for one that wasn't in his name. It didn't work.

He's now charged by the Justice Department and the CFTC, the first insider-trading case the commodities regulator has ever brought over these event-betting contracts. The legal hook is a provision so on-the-nose it has a nickname: the "Eddie Murphy Rule," named for the climax of Trading Places, written into law to stop people from cashing in on government information they had no business trading on. Three of the counts each carry up to ten years.

Anatomy of a $409,000 bet
Master Sgt. Gannon Ken Van Dyke, U.S. Army Special Forces
December
Read into Operation Absolute Resolve, the mission to capture Maduro. Sits through a classified briefing; signs an NDA.
~2 weeks later
Opens a Polymarket account.
Late Dec–Jan 2
Loads up on "Yes" — hundreds of thousands of shares betting Maduro is gone by end of January.
Jan 3
U.S. forces raid Caracas and take Maduro. The bets resolve; he starts pulling out ~$409,000 that day.
After
As people flag the perfect trades, he allegedly tries to delete his account. It didn't work — three counts now carry up to 10 years each.

And here's where the whole thing curdles into something bigger than one greedy sergeant.

Polymarket isn't supposed to take American money at all. Four years ago it paid regulators $1.4 million and formally barred U.S. users. But a VPN is a five-dollar workaround a teenager can manage, and the company itself says all the right things — that insider trading isn't welcome and that anyone who tries it will be found. Maybe. Meanwhile, more than a billion dollars has been staked online this year alone on military decisions and outcomes. A billion dollars riding on the question of whether and when this country goes to war.

Think about what that actually does. It takes the most consequential decisions a government can make — the ones measured in human lives — and quietly attaches a payout to them. It builds a financial constituency that profits when the missiles fly. And it dangles, in front of every official and planner and analyst and overheard spouse, a tax-free reward for being the first to whisper. We have always worried about people who want war for ideology, or for politics, or for contracts. This is something newer and dumber and somehow worse: people who can simply make money on the timing, the way you'd make money knowing a company's earnings before they're announced.

The market, in the end, is honest about one thing. It put a price on it. And the price tells you that somewhere out there, before the rest of us heard a single word, somebody always knew first.

The New Insiders · A two-part investigation
Insider betting on the real world — first on war, now on elections.
Part 1 · You’re reading thisThe People Betting on War Keep WinningLongshot bets on U.S. military strikes win 52% of the time. Someone always knows first.
Part 2The Other Insiders: Betting on Their Own CandidatesOperatives wagering on the races they run, with polls the public can’t see yet.
Business prediction markets Polymarket Insider trading Venezuela