The average guys outsmarting Wall Street
Making millions wagering on everything from war to Rotten Tomatoes
The New York Times Magazine
May 31, 2026

Adam Iscoe begins his piece in this week’s magazine by observing that, among the young men of his generation, “everyone’s got a little money riding on something.” These days, that often happens on prediction market platforms like Polymarket and Kalshi, where users wager on what will happen in the future, whether election results, military strikes or Rotten Tomatoes scores. Iscoe and his peers usually bet “a little”; they also usually lose a lot. But there is a small class of traders, known as “sharps,” who make six and seven figures by hoovering up “dumb money” from amateurs, otherwise known as “newbies,” “fish” or “squares.”

The sharps are self-taught traders who gain their edge from research. Iscoe speaks to many of them about their methods, even spending time with a group as they conduct their own door-to-door poll for the Democratic Senate primary in Texas. But while the sharps are a new breed of financial maven — operating independently in a Wild West that lawmakers want to regulate — Iscoe wonders if they’re all that different from Wall Street traders. “Me and the banks are doing the same thing,” one sharp tells him. “I think it says more about the market than it does about me. They can’t beat an acting major in a garage with Excel.”

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49 MIN LISTEN

The Average Guys Outsmarting Wall Street on Prediction Markets

How prediction market “sharps” have made millions wagering on everything from war to Rotten Tomatoes.

By Adam Iscoe

THIS WEEK’S COVER

To create this week’s cover image, the magazine took an image of the A.I. actress Tilly Norwood, pasted it into ChatGPT and prompted the app to make slight adjustments to the facial expression. The results were shared with Particle 6, the production company behind Norwood’s creation, which further refined the image.

GENERATED BY A.I.

FROM THE ARCHIVES

If You Can’t Spot the Sucker

Before Polymarket and Kalshi, before the Supreme Court struck down the ban on sports gambling in 2018, the early seeds of modern online betting markets were planted with the emergence of “daily fantasy sports.”

Ten years ago, Jay Caspian Kang wrote about how DraftKings and FanDuel spent over $200 million to advertise their daily fantasy offerings, in a feature titled “How the Daily Fantasy Sports Industry Turns Fans Into Suckers.” Does any of this sound familiar?

I came across a different sort of problem: a rapacious ecosystem in which high-volume gamblers, often aided by computer scripts and optimization software that allow players to submit hundreds or even thousands of lineups at a time, repeatedly take advantage of new players, who, after watching an ad, deposit some money on DraftKings and FanDuel and start betting. Both companies mostly looked the other way.

The betting economy that has been created is highly unstable and corrupt. One critic I spoke to was Gabriel Harber, a well-known D.F.S. podcaster and writer who has worked in the D.F.S. industry since its inception and goes by the handle CrazyGabey. He has come forward to discuss the rampant exploitation in D.F.S.’s betting economy. “The idea that these sites exist so that regular guys can make a lot of money playing daily fantasy sports is a lie,” Harber told me.

“Your average Joe sees a commercial for daily fantasy sports, signs up, plays and loses,” Harber wrote. “He has no idea his games are being sniped by professional power users with access to automated processes and optimization software. He has no idea that the large-field tournament he’s playing in features power users with hundreds of unique lineups, all optimized using third-party software. In truth, D.F.S. is more like the stock market, with athletes instead of commodities. No new player attempting to trade stocks has any shot at success without a sizable amount of training.”

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COMMENT OF THE WEEK

‘I Want to Take His Face… Off.’

From J on David Marchese’s interview with Nicolas Cage:

Back in about 2000, I met a beautiful Frenchwoman on the plane from Paris to New York. She was on her way to America for the first time. She told me she had learned English by watching a VHS tape of “Face/Off” hundreds of times as her only source material. I fell deeply in love. Her English wasn’t great, but was very Cagesque.

That’s all for this week. Email us at magazine@nytimes.com with your thoughts, questions and feedback.

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