Polymarket: How to profit from selling classified information | If You're Listening

How closely do you watch big speeches by Donald Trump?I must admit, I don't watch them that closely these days.If something important happens, I'm sure someone will let me know.

An honour.

But on the prediction market websites, Polly Market and Kelshi, there's a small community of people watching speeches like this year's State of the Union very closely indeed.See, both those websites offer what's called mention markets, where people can bet on what Donald Trump will say during his speech.

Speaker Johnson, Vice President Vance, First Lady of the United States.

As Trump began speaking, hundreds of people on Kelshi were placing bets on 56 different words that Trump might say.I've made a chart tracking Kelshi's odds of him saying each of the 56 words.It's a bit of a mess obviously, but it'll make sense in a second.For example, as he began talking, people thought it was pretty likely that he would say the number 250 when talking about America's 250th anniversary celebration in July.And what do you know?

American independence.

There you go.The word trillion was also considered very likely to be mentioned and...

The last administration got less than one trillion dollars in new investment in the United States.

The thing is betting on likely words isn't very profitable.If you put a hundred bucks on trillion as he was getting up to speak, you would have made a profit of two dollars.The big money is in more unlikely words.Like, would Trump say no, no, no?as in the word no repeated three times consecutively.Before the speech this is thought that there was a 24 % chance of him saying that so a hundred dollar bet on it would get you a profit of 316 dollars.

You'd be quadrupling your money.

But now we're winning too much.And I say, no, no, no.You're going to win again.

Some words considered essentially a sure bet, like coal, he didn't say at all.But the thing about speeches like this is Trump isn't just riffing for 108 minutes.There is a speech written for him.It is loaded into the teleprompter for him to read.The guy who does that is named Gabriel Perez.He has been working for Donald Trump ever since Trump's 2016 presidential campaign staff found his company, VIP Prompters, on a Google search for Teleprompters New York.

He sets up loads and operates Trump's teleprompters.

Well, the president's longtime teleprompter operator is under investigation for insider trading.

But of course, the man is being investigated for allegedly placing bets on his speeches on the prediction market.

The trades reportedly spanned more than a dozen high profile addresses over a three month period, allegedly making him more than 100000 US dollars.They include the state of the union address, and remarks the president made at the World Economic Forum in Davos.

It was a pretty big mistake for this guy to allegedly make these trades on Calshi.While Calshi is the most popular prediction market platform in the US, it also claims to be the most reliable.When they clocked what this guy seemed to be doing, they alerted authorities immediately.Most of the betting on political stuff happens on Calshi's more roguish, unregulated website.Polymarket.And on PoliMarket, stuff like this teleprompter scandal is happening pretty frequently.

A soldier was arrested and is going to be on trial.He was on the team that went into Venezuela and captured Nicolas Maduro.And he allegedly bet on this at PoliMarket.

As Master Sergeant Ganon Ken Van Dyke was on his way into Caracas to capture the Venezuelan president, he was also betting that Maduro would be out of power by the end of that month and What do you know?

A bound and blindfolded Maduro now awaiting trial at a detention center in New York with his wife.

Van Dyke allegedly made nearly $450 ,000 on a $40 ,000 bet.Calshi and Polymarket are exploding in size, influence and popularity.And as they do, more and more insider trading is being identified.These platforms are creating something new that we haven't really had before.It's an easy way to make money from secrets.It's a marketplace for espionage.

Today, the bizarre story of how this prediction market industry got started and the ways it's now potentially causing serious security problems.I'm Matt Bevan, and this is If You're Listening.I am never going to climb Mount Everest and that's for a whole lot of reasons but there's one reason in particular.

The worst part for me was probably about three hours into our summit climb there was a lifeless body attached to the anchor and every single person that was heading to the summit had to step over that human being.

Yes, Mount Everest is covered in human corpses.I saw five bodieson the way up.One I sat next to for a while, not realising that I was sitting next to a corpse in the snow.

There are hundreds of these bodies, entirely intact, but completely frozen.They look like they're sleeping, but they are very much dead.And one of these bodies is particularly interesting to me.Up near the summit is the body of an Irishman named John Delaney.He was the boss of the company Intrade, which gained a lot of attention about 20 years ago for its apparent ability to predict the future.

Wouldn't you like to predict the future?Like who will be the next president?Well, there's a website that makes more accurate predictions than any I've ever come across.InTrade was a betting website.

It enabled people to place bets on the outcome of all sorts of events.

Obviously, you can bet on political races, weather events, everything around the world on your website.

Delaney was a regular on business news channels like CNBC talking about what his members were betting on.

in 2008.Earlier today it reached an all -time high of around 75.

He pitched his website as not only something that people could use to make money, but something that people could use to help others.predict the future by harnessing what he called the wisdom of crowds.

When you aggregate information from a very diverse, large community or crowd of people, then typically the information that you aggregate has the opportunity to be smarter than any one individual.

InTrade became the world's largest prediction market, which was a deliberately chosen phrase to differentiate it from a gambling website, whichin America is heavily regulated.Delaney argued that his company was different from traditional gambling operations because there was no house.In traditional betting, people bet against a licensed bookmaker, whereas on Intrade, the users were just betting against each other.But US regulators weren't convinced.The trouble is, betting like this is ripe for corruption.

When you're betting on sports or election results, the outcome is generally inherently unpredictable.But when you bet on the outcomes of things that a few people already know, it starts to get a little weedy.The regulators said they weren't necessarily against the idea of betting on things other than sports, as long as it was fair.

To me there's no reason why you shouldn't be able to bet on the Oscars or bet on the presidential race because it's regulated and as long as the system can't be gamed.

But Intrade wasn't regulated and the system could be easily gamed.They had to base themselves in Ireland and Delaney himself was told he would be arrested if he entered the United States.If you came to the United States, you might be locked up.I've been told I don't look good in an orange jumpsuit.So Intrade had a few problems.One being that despite the attention it got from the media, it was surprisingly small.

While it had a lot of users, they were spread out across so many different types of bets that there wasn't all that much money to be made in any of them.In economics terms they didn't have a lot of liquidity in them.While Delaney may have been promising that the website was based on the wisdom of crowds, that only works if you've got a crowd of people betting.Most in -trade markets were very small and odds could be moved by one or two relatively small bets.Another problem waswas the money.

While Intrade was handling a lot of money transferring it through their system and to and from their users, it wasn't actually making very much money.So how do you solve these problems?Well becoming a white -collar criminal is definitely an option and it seems that John Delaney did just that when he started to transfer money out of the accounts of people betting on his site and into his own.A bit more than two million dollars in total was apparently pilfered.But before anyone found out what he was up to, Delaney joined a Russian expedition to climb Mount Everest and died 50 meters from the summit.The following year, the company collapsed.

Intrade is leaving the U .S.market.The decision was announced on the 26th of November in a letter to U .S.account holders.

Intrade cited regulatory concerns and mounting legal pressure in their decision to pull out.

So that's the story of the OG prediction market company Intrade.PolyMarket and Calshi are back.incredibly similar to their Irish predecessor, apart from a few tweaks to try and fix some of Intrade's inherent issues.Kalshi is essentially just Intrade, but based in America and extremely transparent with government regulators.They gleefully dob on people they suspect of any sort of dodginess.Polymarket, though, is technically based in Panama for legal reasons, but its bosses live in the US, lobbying government officials and regulators in an effort to stay in business.

To fix the small liquidity and revenue problem, Cauchy and Polymarket have been spending hundreds of millions marketing themselves to Americans in order to try and pull in users.

Both Polymarket and Kalshi have used outlandish marketing tactics to cut through including giving away groceries and AI generated ad campaigns.

And the marketing seems to be working.The industry is worth, you know, more than $20 billion a year in the US, despite the fact that it barely existed just a few years ago.And both companies have taken steps to stop unscrupulous Irish mountaineers from raiding their tills.Calshi has invited regulators to examine their books, and Polymarket has enabled users to trade directly with each other using cryptocurrency.So Polymarket and Calshi have addressed most of the issues that led to the downfall of intrade, which is great.But Polymarket in particular has created an entirely new problem.

See, by allowing people to trade with cryptocurrency, they are letting people make money anonymously.And that promise of anonymity is inviting some people into the market that really shouldn't be there.With that in mind, I want to introduce you to a Polymarket user whose handle on the website is MAGAMYMAN.See, while Polymarket does allow users to set up anonymous accounts, the activity of each of those anonymous accounts is available publicly on the internet for anyone to look at.So while I don't know anything about MAGAMYMAN personally, apart from potentially his political tendencies, I do know all about what he's been betting on since starting his account in October 2024.In that time, MagaMyMan has made bets on dozens of different things, generally to do with geopolitics and financial markets.

But the interesting thing is his success varies wildly by topic.He isn't good at predicting what the stock market will do or whether Bitcoin will go up or down or who will win elections.One thing he is exceptionally good at is predicting when Iran is going to get bombed.In the first week of October 2024, when he opened his account, he put on a bunch of bets that Israel would not launch a military strike on Iran that week.This was an interesting bet because just days earlier, this happened.

Bright lights streak through the sky as dozens of missiles rain down over Israel.

After earlier Israeli attacks, which decimated the leadership of Iranian -backed militias Hamas and Hezbollah, Iran had been firing missiles into Israel.It was extremely scary.Nothing that we could have anticipated.And a lot of people expected Israel to respond, but not Maga My Man.In fact, he was so confident, he put about $20 ,000 down in bets that Israel would not retaliate that week.The way these bets work is you're buying shares in a contract that will pay $1 to whoever answers a question correctly.

In this case the question was, will Israel respond militarily to Iran by Sunday?You can either bet yes or no to that question.When Magomayman bought his first tranche of no shares, he bought them at 89 cents each, meaning that if Israel did not bomb Iran that week, he would get one dollar back for every 89 cents he spent.When nothing happened,the account made about $3 ,800.Not bad for a bet on nothing happening.

In the second week of his polymarket account, he didn't make any bets at all.Then at the start of the third week, he bought $40 ,000 worth of yes shares, predicting that an Israeli strike was imminent.

And...Several powerful explosions have been heard near Tehran.

when a promise to attack becomes reality.The Israeli Defence Force is soon confirming it had begun its long -awaited strikes.

This time he won big, turning an $82 ,000 profit.By the end of the year he was up $93 ,000.2025 was much quieter.He made a few bets here and there on local elections and whether the price of Bitcoin would go up or down and federal interest rate decisions.Most of the bets didn't go all that well for him.By year's end, he had made a profit of a little over $5 ,000.

But then in 2026, things got much more interesting when news reports started circulating about the Iranian regime killing thousands of protesters on the streets of various cities.and the White House started making threats.

The president and his team have communicated to the Iranian regime that if the killing continues, there will be grave consequences.

Maga My Man's account sprang to life again, dumping $400 ,000 into an interesting mix of bets.One was a series of small yes bets that the US would begin striking Iran that month.The other was a series of comparatively larger no bets, saying that Israel would not strike Iran that month.So he was betting that the U .S.would launch attacks, but Israel would not.

By the end of that month, nothing happened.No attacks were launched by either side.But that was okay, because his winnings betting on Israeli inaction outweighed his losses.But by mid -February... things started getting even more interesting.

CBS News has exclusively learned the US military could strike Iran as soon as Saturday.Could happen this weekend, could happen next week, might not happen at all.

Despite increasing hype over a potential mid -February attack, Maga My Man was confident that it wouldn't happen that month either.In fact, he was so confident that he started laying on some big bets, including $224 ,000 on the strike not happening in February at all.And then he placed another bet of $61 ,000 that the strike would happen by the end of March.This represented a massive shift in his activity.Throughout 2024 and 2025, he had made bets totaling $228 ,000 on Polymarket.But now he was dropping that kind of money on a single weekend.

By the afternoon of the 26th of February, Donald Trump still wasn't quite sure what he was going to do.But he wanted the military to be ready for it if he decided to attack Iran.

It'd be nice if we could do it without, but sometimes you have to do it with.

He told the military to make preparations and wait for a final go order from him.Maga My Man started putting an additional 200 grand on the strike happening in March.He took money out of his other bets in order to maximise his position.The rest of the market started moving too.Lots of people seemed to think that March might be going to happen.But then, at 3 .38pm on the 27th of February, Trump pulled the trigger.

The president directed, and I quote, Operation Epic Fury is approved.No aborts.Good luck.Close quote.

And the thing here is most of the people on Polly Market didn't react at all.But MAGA My Man did.Just before midnight Washington time, he began frantically placing bets on a February strike.He started buying up shares on before the end of March, too, because February technically is before the end of March.Over a period of half an hour, he dumped an extra 100 grand into a market that had no idea that anything was happening.

As dawn crept up across the Central Command AOR, the sky surged to life.More than 100 aircraft launched from land, sea, fighters, tankers, airborne early warning, electronic attack, bombers from the States and unmanned platforms forming a single synchronised wave.

As the bombs rained down on Iran, Maga My Man and a few other people, who just happened to place bets at the exact right moment, began to collect their winnings.

A number of punters have reportedly made about a million US dollars by correctly predicting when the United States would strike Iran at the weekend.

Now, I don't know who these guys are.Maybe they work in intelligence agencies.Maybe they work on US military bases.Maybe they work in the White House itself.We don't exactly know, but we could kind of take a guess about why people might have suddenly decided to bet a lot of money on that.Understandably, there were a lot of questions about how these folks managed to get so lucky.

But as of July 2026, nobody has been charged in relation to this.And you might say, well, maybe Maga My Man is just really good at this stuff.When you look at his account in its entirety across all of thethe trades that he's made over the last couple of years it seems like there are two entirely different people making the bets.There's the normal poly market trader dabbling in political bets and then there's the one who seems to know ahead of anyone else explicitly when Iran is about to get bombed.If you separate the Iran bets from the non -Iran bets, the contrast could not be clearer.

He has made $800 ,000 in bets on Iran over the course of 21 months.In terms of bets on non -Iran things, he's lost about $20 ,000.Now most polymarket users are the second kind.the kind who bet on random things based largely on vibes and end up losing money.In fact, barely anyone who uses these sites makes any money at all.

A recent analysis by the Wall Street Journal found that 70 % of polymarket users lose money, with just 0 .1 % of accounts taking 67 % of the profits.

In fact, Maga My Man's success on Iran bets has landed him in the top 0 .05%.of the most successful traders on Polymarket.And MegaMyMan isn't alone in his betting trends.Many of the accounts in the top ranks of Polymarket traders are making a whole lot of coin, making similarly niche and specific bets, generally hidden in a forest of normal, uninformed trades.Anyone who isn't just blatantly opening an account exclusively through a few naughty trades on the one thing they know about, is pretty much flying under the radar.So what are the rules here?

Are there even rules?Well theoretically, yes.If there's one thing that traditional betting companies and government can't do,regulators could agree on over the last few decades, it's that prediction markets like Intrade, Kalshi and Polymarket are just gambling companies wearing a fake beard and glasses to avoid having to comply with gambling laws.Polymarket is banned in lots of countries, including Australia.It was banned in America, too, though millions of Americans found it pretty easy to get access to it anyway.

In 2024, under the Biden administration, the boss of PolyMarket found himself in a bit of legal hot water.

Hot topic of the hour, the CEO of PolyMarket, New York City home, raided by the FBI.

But under the Trump administration, things have changed and PolyMarket doesn't seem to be having nearly as much trouble.Investigations into PolyMarket launched under the Biden administration were quietly dropped in 2025, and I'll let you take a few guesses why.The agency that is meant to police all of this, the Commodity Futures Trading Commission, is built to run on five commissioners.But right now, it only has one, a Trump appointee named Mike.

CFTC Chairman Mike Seelig here.Over the past year, American prediction markets have been hit with an onslaught of state -led litigation.

Mike's decided to try and protect the prediction markets from intervention by state governments across America.

Prediction markets aren't new.They provide useful functions for society by allowing everyday Americans to hedge commercial risks.They also serve as an important check point.on our news media and our information streams.

He says prediction markets are a way for people to check if the media is lying to them.

To those who seek to challenge our authority in the news.let me be clear.We will see you in court.

So regulation seems to be sorted.And now anonymous accounts are making huge amounts of money based on often highly confidential information without any real repercussions.So what has all this deregulation created here?Well, on the one hand, it's just another gambling platform, really not all that much different from sports betting sites.But on the other hand, you've got an industry offering increasingly large amounts of money for secret information.Back in the olden days, by which I mean like two years ago, if you wanted to make money through information you got through your work or connections, you had to find someone who was interested in paying you for it.

But now there's an app available on your phone which is offering money for anything you know that other people don't, as long as it's about an interesting topic.Do you know the details of an upcoming product launch?Do you know what is going to be said during an important speech?Do you know when a military operation is set to begin?

This is a national security risk now, right?We have people trading on what our armed forces are doing and perhaps sending signals out into the world about what our military is going to do.

It's not good.The amount of liquidity in PolyMarket is increasing exponentially.It grew from $8 billion in May to nearly $14 billion a month later in June.More and more people are betting on more and more things, meaning people with insider information have more and more opportunities to make more and more money.So with all this deregulation, the Trump administration has created a market for espionage.Meanwhile, even his own staff cashing in.