Pod Insights If You're Listening How to get away with selling classified information About this episode There's a Polymarket account called Magamyman that's terrible at picking elections, but it's made $800,000 betting on exactly when the US would strike Iran, cashing in within minutes of the bombs actually falling… and it’s not alone. Donald Trump's own teleprompter operator is under investigation for betting on his boss's speeches, and a US soldier allegedly bet on capturing Nicolas Maduro days before doing it himself.
Prediction markets like Polymarket and Kalshi have exploded into a $20 billion industry, and they're built on a simple promise: that crowds are smarter than any individual, and secrets are worth cashing in on. But, with Trump's own son advising both platforms and regulators standing down, who's actually watching for insider trading?
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Transcript 0:00 Speaker 00 ABC Listen, podcasts, radio, news, music and more.
0:08 Speaker 01 Hi, I'm Patricia Carvallis, the host of Politics Now. And throughout the week on the podcast, I'm joined by the brightest political minds at the ABC to wade through the political spin and bring you the analysis you need to know. We go beyond the headlines, digging into the key political stories of the day and making sure we have a little bit of fun along the way. I don't think it's an aberration. I don't think it's just rogue. I don't think it's just temporary. I think politics is being smashed and anyone who thinks that it's just a passing thing is completely deluded.
0:42 Speaker 02 Delulu, you reckon?
0:43 Speaker 01 Delulu. It's called Politics Now and you can find it on ABC Listen.
0:47 Speaker 03 This podcast was produced on the lands of the Uabakal and Gadigal people. How closely do you watch big speeches by Donald Trump?
0:56 Speaker 04 Mr Speaker, the President of the United States.
1:01 Speaker 03 I must admit, I don't watch them that closely these days.
1:08 Speaker 03 If something important happens, I'm sure someone will let me know.
1:12 Speaker 05 Well, thank you very much, everybody. It's really an honour.
1:16 Speaker 03 But on the prediction market websites, Polymarket and Kalshi, 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.
1:37 Speaker 05 Speaker Johnson, Vice President Vance, First Lady of the United States.
1:46 Speaker 03 As Trump began speaking, hundreds of people on Kalshi were placing bets on 56 different words that Trump might say. 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?
2:08 Speaker 05 The 250th anniversary of our glorious American independence.
2:16 Speaker 03 There you go. The word trillion was also considered very likely to be mentioned and?
2:22 Speaker 05 The last administration got less than $1 trillion in new investment in the United States.
2:29 Speaker 03 The thing is, betting on likely words isn't very profitable. If you put £100 on trillion as he was getting up to speak, you would have made a profit of $2. 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, bettors thought that there was a 24% chance of him saying that. So a $100 bet on it would get you a profit of $316. You'd be quadrupling your money.
3:04 Speaker 05 Now we're winning too much. And I say, no, no, no, you're going to win again.
3:13 Speaker 03 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 and, well...
3:47 Speaker 06 The president's longtime teleprompter operator is under investigation for insider trading.
3:53 Speaker 03 But of course.
3:54 Speaker 07 The man is being investigated for allegedly placing bets on his speeches on the prediction market Kalshi.
4:01 Speaker 03 It was a pretty big mistake for this guy to allegedly make these trades on Kalshi. While Kalshi 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 Kalshi's more roguish, unregulated rival, Polymarket. And on Polymarket, stuff like this teleprompter scandal is happening pretty frequently.
4:35 Speaker 04 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 Polymarket.
4:47 Speaker 03 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?
5:00 Speaker 06 Abound and blindfolded Maduro, now awaiting trial at a detention center in New York with his wife.
5:07 Speaker 03 Van Dyke allegedly made nearly $450,000 on a $40,000 bet.
5:16 Speaker 03 Kalshi 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.
5:49 Speaker 03 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.
6:15 Speaker 03 I am never going to climb Mount Everest, and that's for a whole lot of reasons. But there's one reason in particular.
6:23 Speaker 06 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.
6:36 Speaker 03 Yes, Mount Everest is covered in human corpses.
6:43 Speaker 03 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. Joining us from Dublin via telepresence, Intrade CEO, John Delaney. John, thanks so much and great to have you with us. 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.
7:15 Speaker 04 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.
7:24 Speaker 03 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.
7:42 Speaker 02 About a month ago, the market was trading at around 48, less than a 50% probability that the US would enter recession in 2008. Earlier today, it reached an all-time high of around 75.
7:55 Speaker 03 He pitched his website as not only something that people could use to make money, but something that people could use to help predict the future by harnessing what he called "the wisdom of crowds".
8:07 Speaker 02 When you aggregate information from a very diverse, large community or a crowd of people, then typically the information that you aggregate has the opportunity to be smarter than any one individual.
8:21 Speaker 03 Intrade became the world's largest prediction market, which was a deliberately chosen phrase to differentiate it from a gambling website, which in 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.
9:03 Speaker 03 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, as long as 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.
9:42 Speaker 02 I've been told I don't look good in an orange jumpsuit.
9:48 Speaker 03 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 Intrade markets were very small, and odds could be moved by one or two relatively small bets. Another problem was the money.
10:31 Speaker 03 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 $2 million 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 metres from the summit.
11:15 Speaker 03 The following year, the company collapsed.
11:18 Speaker 06 Intrade is leaving the US market. The decision was announced on the 26th of November in a letter to US account holders. Intrade cited regulatory concerns and mounting legal pressure in their decision to pull out.
11:36 Speaker 03 So, that's the story of the OG prediction market company, Intrade. Polymarket and Calshi are incredibly similar to their Irish predecessor, apart from a few tweaks to try and fix some of Intrade's inherent issues. Calshi is essentially just Intrade but based in America and extremely transparent with government regulators. 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, Calshi and Polymarket have been spending
12:18 Speaker 03 hundreds of millions marketing themselves to Americans in order to try and pull in users.
12:24 Speaker 05 Both Polymarket and Calshi have used outlandish marketing tactics to cut through, including giving away groceries.
12:34 Speaker 05 And AI-generated ad campaigns.
12:38 Speaker 03 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.
13:24 Speaker 03 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.
13:41 Speaker 03 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 Maga My Man 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, Maga My Man 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,
14:25 Speaker 03 or whether Bitcoin will go up or down, or who will win elections. But the 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.
14:57 Speaker 00 Bright lights streak through the sky as dozens of missiles rain down over Israel.
15:03 Speaker 03 After earlier Israeli attacks, which decimated the leadership of Iranian-backed militias Hamas and Hezbollah, Iran had been firing missiles into Israel. 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.
15:48 Speaker 03 When Maga My Man 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 $1 back for every 89 cents he spent. When nothing happened, the account made about $3,800. It's not bad for a bet on nothing happening.
16:14 Speaker 03 Two weeks later, he bought $40,000 worth of yes shares, predicting that an Israeli strike was imminent, and...
16:23 Speaker 06 When a promise to attack becomes reality, the Israeli Defence Forces soon confirming it had begun its long-awaited strikes.
16:32 Speaker 03 This time, he won big, turning an $82,000 profit. By the end of the year, he was up 93 grand.
16:42 Speaker 03 2025 was much quieter. He made a few small bets here and there, but most of them didn't go that well. 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 Myman dumped $40,000 into an interesting mix of bets. One was a series of small yes bets
17:25 Speaker 03 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 US would launch attacks in January, but Israel would not. By the end of that month, nothing had happened. But by mid-February, things started getting even more interesting.
17:51 Speaker 04 CBS News has exclusively learned the US military could strike Iran as soon as Saturday.
17:57 Speaker 06 Could happen this weekend, could happen next week, might not happen at all.
18:00 Speaker 03 Despite increasing hype over a potential mid-February attack, Maga Myman 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 grand on the strike not happening in February at all. And then he placed another bet of 61 grand that the strike would happen by the end of March.
18:28 Speaker 03 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. MAGA My Man started putting an additional 200 grand on the strike happening in March. The rest of the market started moving too. Lots of people seemed to think that March might be going to happen.
19:08 Speaker 03 But then, at 3:38pm on the 27th of February, Trump pulled the trigger.
19:14 Speaker 05 The president directed, and I quote, "Operation Epic Fury is approved. No aborts. Good luck."
19:20 Speaker 03 And the thing here is, most of the people on Polymarket didn't react at all. But MAGA My Man did. Just before midnight, Washington time, he began frantically placing bets on a February strike. Over a period of half an hour, he dumped an extra 100 grand into a market that had no idea that anything was happening.
19:47 Speaker 05 As dawn crept up across the Central Command AOR, the skies 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 synchronized wave.
20:07 Speaker 03 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.
20:18 Speaker 04 A number of punters have reportedly made about $1 million by correctly predicting when the United States would strike Iran at the weekend.
20:26 Speaker 03 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. 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 twenty twenty six, nobody has been charged in relation to this. And you might say, well, maybe Maga My Man is just really good at this stuff. But when you look at his account in its entirety, across all of the trades that he's made over the last couple of years,
21:07 Speaker 03 it seems like there are two entirely different people making the bets. There's the normal polymarket 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 them, the Iran bets from the non-Iran bets, the contrast could not be clearer. He has made eight hundred thousand dollars in bets on Iran over the course of twenty one months. In terms of bets on non-Iran things, he's lost about twenty grand.
21:45 Speaker 03 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.
22:00 Speaker 05 A recent analysis by the Wall Street Journal found that seventy percent of polymarket users lose money, with just point one percent of accounts taking sixty seven percent of the profits.
22:12 Speaker 03 In fact, Maga My Man's success on Iran bets has landed him in the top zero point zero five percent of the most successful traders on polymarket. And Maga My Man 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.
22:54 Speaker 03 So what are the rules here? Are there even rules? Well, theoretically, yes. If there's one thing that traditional betting companies and government gambling 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. The hot topic of the hour, the CEO of Polymarket, New York City home raided by
23:39 Speaker 03 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.
23:57 Speaker 04 Donald Trump Jr. is an advisor to both Polymarket and Kalshi. It's not exaggeration to say none of this would have happened without the Trump administration.
24:06 Speaker 03 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.
24:18 Speaker 05 CFTC Chairman Mike Selig here. Over the past year, American prediction markets have been hit with an onslaught of state-led litigation.
24:28 Speaker 03 Mike's decided to try and protect the prediction markets from intervention by state governments across America.
24:35 Speaker 05 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 on our news media and our information streams.
24:49 Speaker 03 He says prediction markets are a way for people to check if the media is lying to them.
24:54 Speaker 05 To those who seek to challenge our authority in this space, let me be clear.
25:00 Speaker 06 We will see you in court.
25:02 Speaker 03 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. The amount of liquidity in polymarket is increasing exponentially.
25:45 Speaker 03 It grew from $8 billion in May to nearly $14 billion a month later in June. 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?
26:04 Speaker 04 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.
26:15 Speaker 03 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.
26:27 Speaker 03 So with all this deregulation, the Trump administration has created a market for espionage. Meanwhile, even his own staff are cashing in.
26:47 Speaker 03 If You're Listening is written by me, Matt Bevan. Supervising producer is Cara Jensen-McKinnon. It's produced by Adair Shepherd. We'll catch you on Tuesday.
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