Polymarket and Kalshi Grapple With A New Class of Insider Trader

Summary

Podcast Summary: "Polymarket and Kalshi Grapple With A New Class of Insider Trader"

Podcast: The Big Take by Bloomberg and iHeartPodcasts
Date: July 20, 2026
Host: Sarah Holder
Guests/Contributors: Denitza Nikolova (Bloomberg Markets Reporter), Leonardo Nicoletti (Data Visualization, Bloomberg)

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Overview

This episode examines the emerging world of prediction markets—platforms like Polymarket and Kalshi, where users can bet on real-world outcomes—and the concerning rise of a new class of insider trading within these exchanges. Through stories, analysis, and expert interviews, Bloomberg’s team explores what counts as “insider trading” on prediction markets, the regulatory and practical challenges these platforms face, and the resulting ethical, legal, and national security implications.

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Key Discussion Points & Insights

1. The Super Bowl Wager: Uncovering Grey Areas (02:13–04:20)

• Story Highlight: TikToker Kaden Booth bet $50,000 on the Super Bowl national anthem duration after camping outside the stadium to time the rehearsal, winning big.
  • “He waited 12 hours in total. And in the end, he managed to be outside on a public sidewalk listening to the rehearsal of the national anthem and timing it with a stopwatch in hand.” — Denitza Nikolova (03:43)
• The wager prompted debate: Was it clever research, or insider trading?

2. Defining Insider Trading in Prediction Markets (05:39–07:33)

• Key Point: Traditional definitions focus on non-public, confidential information. Prediction markets extend this to “binary outcome contracts” on nearly any event.
  • “Rules are not ready for binary outcome contracts on pretty much everything in the world. There are so many platforms… users have been getting more sophisticated.” — Denitza Nikolova (05:14)
• Platforms differ: Kalshi (US-based, CFTC-regulated, identity verification) vs. Polymarket (global venue, sometimes unregulated, anonymous accounts).

3. Detecting Suspicious Activity: The Polysites Analysis (08:00–10:08)

• Tech Insight: Bloomberg, with data firm Polysites, analyzed ~34,000 Polymarket trades, focusing on metrics flagging likely insider trading (account creation timing, trade size, market focus).
  • “If they open an account and then five minutes later they put a $20,000 bet on something very specific, they would score really high on that metric.” — Leonardo Nicoletti (08:15)
• Increase in flagged, potentially insider trades—especially on topics with geopolitical implications.

4. National Security, Geopolitics, and Ethics (10:15–12:48)

• Examples: Bets concentrated on conflicts (Iran, Venezuela, US military strikes).
• Case Study: Gannon Ken Van Dyke, US soldier, indicted for allegedly trading on classified info about Venezuelan leadership.
  • “He profited more than $400,000 on the ouster of Venezuelan President Nicolas Maduro... a massive national security risk.” — Denitza Nikolova (11:19)
• Both market scale and lack of prior crackdowns create “a whole new world of opportunities.”

5. The Debate: Are Insider Trades Good for Prediction Markets? (12:48–14:03)

• Insider Trading as Truth?: Some, like theorist Robin Hanson (“the godfather of prediction markets”), argue knowledgeable insiders improve accuracy.
  • “If our goal is to find information, if you want to find what is the outcome of a certain event, if we actually have knowledgeable participants, that is good for us.” — Denitza Nikolova (12:58)
• The Risks: Critics say it’s unfair to average users and creates incentives for manipulation or even compromising national security.

6. How Platforms and Regulators Are Responding (17:52–21:05)

• Recent Cases: A White House teleprompter operator made $100,000+ betting on Trump’s speeches; flagged and reported by Kalshi to the CFTC.
  • “Kalshi flagged the suspicious activity to the Commodity Futures Trading Commission.” — Sarah Holder (17:52)
• Platform Efforts:
  • Kalshi and Polymarket both claim to refer suspicious cases to authorities.
  • Kalshi bans politicians from betting on their own elections and screens for employment info.
  • Polymarket’s US exchange restricts most contracts; international exchange remains largely unregulated.
  • “Polymarket's direct response… was that they have referred 100 cases to law enforcement.” — Denitza Nikolova (19:18)

7. Regulatory and Enforcement Challenges (21:05–23:34)

• Regulatory Turf Wars: Disputes between CFTC and states; primary authority currently lies with CFTC.
• Polymarket's Ambiguous Reach:
  • US users technically banned from using international exchange; many still access via crypto (e.g., Coinbase).
  • Of $21 billion+ in Polymarket trades, ~half trace back to US crypto exchanges; in geopolitical markets (e.g., Iran), this jumps to 70%.
  • “Flagged trades related to the Iran war markets since last July are almost three times as likely to have been funded through US regulated cryptocurrency exchanges.” — Leonardo Nicoletti (22:22)

8. The Cat-and-Mouse Game: Future Outlook (23:34–24:42)

• Practical Limits: Gaps in employment and political data make enforcement tricky. Information can be traded second/thirdhand, complicating investigations.
  • “A lot of the insider trading we see is not directly done by the person who has the insider information… that information can be passed on.” — Denitza Nikolova (23:34)
• Prediction: As platforms get better at monitoring, so do would-be insider traders. The game never ends.

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Notable Quotes & Memorable Moments

• “If I can make money on a market that is connected with violence, with attacks, terror, and all that, if I have an incentive to do that, that gets pretty dark, right?”
  — Denitza Nikolova (04:54)

• “If our goal is to find information … having insider traders in that market is going to help you find the truth.”
  — Paraphrasing Robin Hanson via Denitza Nikolova (12:58)

• “It just becomes very, very hard to investigate. It becomes even harder to bring a lawsuit and it just brings a whole level of complications… more regulation… more sophisticated platforms… traders get more sophisticated. So it's a constant game of catching up. Yeah, cat and mouse. It never stops.”
  — Denitza Nikolova (23:34)

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Timestamps for Key Segments

• Super Bowl Prediction Market Example: 02:13–04:20
• Defining Prediction Market Insider Trading: 05:39–07:33
• How Polysites Flags Suspicious Trades: 08:00–10:08
• National Security and Geopolitics Case Studies: 10:15–12:48
• Debating ‘Good’ vs. ‘Bad’ Insider Trading: 12:48–14:03
• Recent Enforcement and Platform Responses: 17:52–21:05
• Regulatory and Enforcement Challenges: 21:05–23:34
• Cat-and-Mouse Future Outlook: 23:34–24:42

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Tone & Takeaways

The episode strikes a mix of fascination and concern. It’s inquisitive about the technological and informational advances that prediction markets enable but candid about the danger posed by unchecked insider trading—especially as the stakes shift from celebrity gossip to national security. The regulatory arms race is just beginning, as both platforms and regulators wrestle with anonymous, international, and highly-motivated parties. As Denitza Nikolova sums up: “It’s a constant game of catching up. Yeah, cat and mouse. It never stops.” (24:42)

Transcript

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[Sarah Holder]

Bloomberg Audio Studios Podcasts Radio News

[Bank of America Representative]

I'm camping outside the super

[Leonardo Nicoletti]

bowl stadium with this listening device.

[Bank of America Representative]

For the next few days, you can

[Denitza Nikolova]

bet on how long the national Anthem will be.

[Sarah Holder]

Back in February, the Tiktoker Kayden booth thought of a way to game the Super Bowl. He wanted to make a wager on the prediction platform Polymarket about how long it would take Charlie Puth to sing the national anthem.

[Denitza Nikolova]

He figured out when the rehearsal for the Super Bowls are happening. He figured out when the artists are flying. He was striking like private jets, other jets and just like figuring out all the travel.

[Sarah Holder]

That's Danita Sekova, a cross asset reporter covering global markets at Bloomberg.

[Denitza Nikolova]

He waited 12 hours in total. And in the end, he managed to be outside on a public sidewalk listening to the rehearsal of the national anthem and timing it with a stopwatching hand.

[Sarah Holder]

Kaden would go on to bet more than $50,000 based on this estimate.

[Bank of America Representative]

So I hammered under 117 seconds and waited till the super bowl to see if we won.

[Sarah Holder]

And on game day, he won big when the anthem came in at 104 seconds. Kaden isn't a casual polymarket trader. He's more like a power user. And his super bowl wager became part of a larger conversation about what constitutes a fair trade on the platform.

[Denitza Nikolova]

So there were so many posts questioning whether this is insider trading. You know, half of the responses were like, oh, this guy's super smart. He went there, he did his job. Nothing is insider. The other people were like, oh, this is pushing things too far.

[Sarah Holder]

Polymarket explicitly forbids betting with stolen or confidential information, relying on illegal tips or or placing wagers on events where you can influence outcomes. CadenceBet didn't appear to cross any of those lines. But a Bloomberg Businessweek analysis of polymarket transactions flagged as suspicious by the analytics firm Polysites found that in the first six months of this year, potential insider trades have been on the rise, especially insider trades with geopolitical implications.

[Leonardo Nicoletti]

We saw that a majority of these trades are concentrated in Iran, war, and Venezuela geopolitical markets.

[Sarah Holder]

That's Leonardo Nicoletti. He's on Bloomberg's data visualization team, and he worked on the analysis with Deniza.

[Leonardo Nicoletti]

There are tens of millions of dollars in bets on those markets, and some accounts, usually a very small share of accounts, have made huge profits on those markets.

[Sarah Holder]

Tanitza says the stakes of using insider knowledge to inform prediction market bets are getting higher than ever.

[Denitza Nikolova]

If I can make money on a market that is connected with violence, with attacks, terror, and all that, if I have an incentive to do that, that gets pretty dark, right?

[Sarah Holder]

And now regulators and the platforms themselves are starting to rethink where the lines between questionable and illegal should be drawn.

[Denitza Nikolova]

We're used to treating insider trading when it comes to bonds, stocks, and like, you know, if I'm a Microsoft employee, it's a common sense that I cannot do so much trading on the stock if I have insider information. So what the rules are not ready for is, like, binary outcome contracts on pretty much everything in the world. There are so many platforms that are tracking this activity, but the users have been getting more sophisticated.

[Sarah Holder]

Foreign. I'm Sarah Holder, and this is the big take from Bloomberg News today on the show prediction markets have opened the door to gambling on everything from celebrity wedding details to the timing of military strikes. They've also created a new kind of insider trader, one that U.S. regulators and the platforms themselves are racing to stop. Leo Denitsa, both of you have been reporting on the wild world of prediction markets. Sites like Polymarket and Kalshi, where people can bet on binary outcomes in the real world. You've specifically been looking at the rise of insider trading on these platforms. So first, how do prediction markets like Kalshi and polymarket define insider trading?

[Denitza Nikolova]

I think the main thing is non public information. It's important how you get it, especially if you get it in a legal way that breaks even more rules. Even tipping, like if I work at a certain company where I have information, I give it to you. That is also considered illegal. But it has changed a lot.

[Sarah Holder]

Tracking suspicious transactions on these platforms can be difficult, in part because it's hard to know who exactly is making these trades. Kalshi is primarily based in the US which means it's regulated by the Commodity Futures Trading Commission. It requires customers to verify their identities to use the site. But polymarket has a US market and an international exchange which isn't regulated by the cftc. That international venue lists contracts that are considered broadly illegal in the States, including on outcomes related to war and terrorism. And it also allows many users to register without an identity check.

[Leonardo Nicoletti]

Polymarket, on one hand, they use blockchain, which means that everything is transparent. You could see every single trade, every amount of money, but there are no identities associated with each account or trade. So that makes it really hard to understand which trade would constitute insider trading or would be reason to invest. Investigate further.

[Sarah Holder]

Right, but Leo, you and Deniza worked with a data analytics platform called Polycites that uses its own metrics for identifying potential insider trades on polymarkets Global Exchange. Walk me through that analysis.

[Leonardo Nicoletti]

What Polycites does is that they basically crunch all this data in real time and they use a set of different metrics where they score each trade according to how likely it is to resemble something. That would be a classic example of insider trading. They're using eight different metrics, including how much money the trader is wagering, how recently their account was created, and how close in time the account creation was to the the time in which they traded. So if they open an account and then five minutes later they put a $20,000 bet on something very specific, they would score really high on that metric.

[Sarah Holder]

The idea being like, why else would they be creating this account unless they knew that they could win a lot of money on a specific bet or

[Leonardo Nicoletti]

that they had very high conviction on that specific bet, so that they created the account specifically to trade on that. And the combination of that and then putting a lot of money into it and trading only one or very few related markets, for example, only trading one Iran war market or three markets that are very similar. These are all things that Polycites uses to score each trade on a scale of how likely it is to be potentially insider trading activity. And so what we did is we examined roughly 34,000 trades accounting for almost $300 million of money wagered. Basically, we found that trades with characteristics often associated with insider activity have become more prevalent on poly markets starting January of this year.

[Sarah Holder]

Leo, what kinds of trades are seeing the most of this kind of activity according to your analysis? And are there any notable examples we should talk about?

[Leonardo Nicoletti]

The main thing that we've observed is that this kind of activity was largely driven, at least this year, by trading on geopolitical markets and geopolitical events. We saw that a majority of these trades are concentrated in Iran, war and Venezuela geopolitical markets like things like US strikes Iran by February 28th or Maduro out by, you know, this date. Right. What we we found is that the daily volume of these, call them flagged trades really spiked and crested in late February where the bets in Iran related markets were highest.

[Sarah Holder]

One high profile case with geopolitical implications involved the US Soldier Gannon Ken Van Dyke, who was indicted in April for allegedly using highly sensitive military information to make money on polymarket. Van Dijk has pleaded not guilty to charges of trading on classified information.

[Denitza Nikolova]

The case is going to court now, but he profited more than 400,000 on the ouster of Van Sorren President Nicolas Maduro. So that was kind of a big case of clearly a national security issue. Right. If soldiers are trading on prediction market and potentially giving signal about their future strikes and their future military action, that's obviously a massive national security risk.

[Sarah Holder]

What did your reporting show about why these are on the rise? Is it just like as these markets grow there are more opportunities? Is it that there are more opportunities to place bets on these huge geopolitical events?

[Denitza Nikolova]

I think it's a combination of both. Like most of those markets didn't exist like year and a half ago and you know, prediction markets weren't really cracking down on this activity as much before. So it kind of created a whole new world of opportunities that wasn't heavily regulated and there was no massive crackdown. And the consequences weren't clear just a year ago. I think it also goes back to how prediction markets were conceived and the initial ideas behind it. A lot of the big theorists behind prediction market actually say that insider trading is good. Insider trading is a signal. So if the supreme purpose of prediction market is to be a truth machine to tell you the future, then having insider traders in that market is going to help you find the truth.

[Sarah Holder]

Teresa, it's so funny you said that proponents of prediction markets say that these insider trades actually help people find the truth. Say more about that argument. Can you explain it?

[Denitza Nikolova]

Yeah, it's really fascinating. So one of the people we have in the story is Robin Hansen, who's kind of the. One of the big theorists behind it. Some people call it the, the godfather of prediction markets. He's spoken to and advised both of the big founders. So Tariq Mansour at Kalshi and then Shane Copeland at polymarket. So the main argument he is that insiders are helping markets. If our goal is to find information, if you want to find what is the outcome of certain event, if we actually have knowledgeable participants, that is good for us. Right, right.

[Sarah Holder]

So his argument is that if you have the insider information, you place a bet that will make the odds more accurate and more reflective of reality. And the fact that there's money on the line just makes the stakes even higher to find the truth. Make the right bet.

[Denitza Nikolova]

Of course. Yeah. There are whole theories of how you can govern a country, how you can govern a. How you can govern so many things using prediction market because they're definitely have been considered a good aggregator for information and a good aggregator of wisdom of the crowds. And in that lines of thinking, insider trading could help.

[Sarah Holder]

Okay, but what about the critics? What are the risks of having an uptick in this kind of insider trading on these prediction markets?

[Denitza Nikolova]

Well, the risks are countless. I mean I don't think it's going to be fun for anyone playing in any market that there are people with knowledge that probably are making prices higher for you. Like I don't think it's fun for trader. It's. I think traders will try to stay

[Sarah Holder]

away and they say it's unfair or it feels unfair.

[Denitza Nikolova]

Yeah, it feels unfair. And they try to stay away from this. Then the bigger questions are there are a lot of market. So the two main thing is manipulation. I shouldn't have incentives to manipulate this. And then obviously national security. I think that's been the massive things. If like US soldiers or any country soldiers are going in prediction market and figuring out and giving signal about their future military plans. It can get pretty dark

[Sarah Holder]

after the break. Kalshi and Polymarket are trying to tamp down on potential insider trading even as users get more sophisticated.

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[Denitza Nikolova]

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[Sarah Holder]

If you're looking for an example of an eyebrow raising prediction market wager, you don't have to go back very far. Just last week, ABC News reported that a teleprompter operator for President Trump had made over $100,000 by betting on more than a dozen presidential speeches. On Kalshee, Kalshi flagged the suspicious activity to the Commodity Futures Trading Commission, ABC reported. At a press conference, White House Press Secretary Caroline Levitt responded to questions about the alleged issue.

[Denitza Nikolova]

I'm aware of the report.

[Sarah Holder]

The President is too. I spoke with him about it.

[Denitza Nikolova]

He believes it's deeply unfortunate and frankly a disgrace. And the individual that was cited in that report is complying with the cftc.

[Sarah Holder]

Levitt said that the teleprompter operator had been put on unpaid administrative leave. If the allegations are proven, a case like this could be a pretty clear cut example of someone with insider knowledge profiting off their access. But Bloomberg's Danit Satsekova says it's also an example of how prediction markets say they're addressing suspicious trades on their platforms by reporting cases to the CFTC or the Department of Justice. In this case, Kalshee did report the suspicious activity to federal regulators. Can you talk more about how Polymarket and Kalshi's approach has differed when it comes to dealing with suspicious trades on their platforms? How did they respond to your reporting?

[Denitza Nikolova]

Yeah, I mean their reaction was that they're doing their best and that they're referring as many cases as possible, which in their defense they are like Polymarket's direct response to this is was that they have referred 100 cases to law enforcement. KI is also they've had some interesting measures to stop that. For example, they've banned a lot of athletes betting on sports. They ask for employment information in certain markets. On Kashi, we've seen a lot of activity from political members and candidates and they have banned Find some Kalshee has

[Sarah Holder]

said that it now screens to prevent politicians from wagering on their own campaigns and athletes from making bets related to their sports, and that it's even collecting employment data from users in some markets to prevent insider trading. In March, Polymarket updated its rules to prohibit trading based on stolen confidential information and illegal tips, as well as wagers by those in a position to influence outcomes. And how are federal regulators approaching this problem?

[Denitza Nikolova]

There is a kind of a regulatory fight in the background between the CFTC and different states about who regulates prediction markets in the first place. I guess the agreement is that currently it's the cftc. So the CFTC has taken a stance mostly critical of Polymarket and their kind of international markets, their global exchange, and them handling so much of the contracts. But at the same time, what we're seeing from the Polymarket exchange in the US is very different. They don't offer most of those contracts that have issues, and also they have a lot more stronger requirements, so they haven't been able to do too much with those markets.

[Sarah Holder]

Polymarket's US Market allows sports and entertainment betting and not much else. But on Polymarket's international exchange, which is illegal to access in the the US Users can bet on virtually anything.

[Leonardo Nicoletti]

The international exchange is not regulated by the cftc, so technically, US People should not be trading on the international exchange.

[Sarah Holder]

Bloomberg's Leonardo Nicoletti.

[Leonardo Nicoletti]

Again, if you try to sign up for polymarket.com within the US you'll get a message that says that you're not allowed to do that.

[Sarah Holder]

But another big challenge for US Regulators looking to crack down on illicit trades is that traders within the US can find ways to illegally access Polymarket International while it's impossible to identify who is trading on the platform or from where. Leonardo's analysis looked at how many trades were funded through crypto exchanges that are regulated in the US like Coinbase. He found that since January 2021, about $21 billion worth of trades on Polymarke were funded through these US regulated crypto exchanges. That's roughly half of all the traceable trading volume on the platform.

[Leonardo Nicoletti]

And the interesting part is that when you look at geopolitical markets, especially for example, the Iran war markets, this percentage goes up to 70%. And then we took our polycytes, flagged trade data, and we found a very similar pattern. Basically, flag trades related to the Iran war markets since last July are almost three times as likely to have been funded through US Regulated cryptocurrency exchanges than through other sources.

[Sarah Holder]

In response to Businessweek's reporting, a Polymarket spokesperson pointed to the global platform's ban on users in restricted jurisdictions. The spokesperson also said, quote, polymarket surveils and monitors for insider trading and other illegal activity, unquote, and said that the blockchain helps both the public and the platform track suspicious traits. This all leads me to my last question, which is just like, how hard is it for prediction markets to actually enforce these rules and what challenges are they going to face as they try to crack down on insider trading moving forward?

[Denitza Nikolova]

I think it's really hard. Like even some of the rules they have already implemented, like for example, tracking political candidates. Even for that there are already some issues because like, all the databases of like, who's involved in a political campaign doesn't necessarily reflect all the people that are involved. And there are gaps. A lot of the insider trading we see is not directly done by the person who has the insider information because obviously that's very risky. But like, that information can be passed, passed on. And then the more people get that information and it's passed on, it just becomes very, very hard to investigate. It becomes even harder to bring a lawsuit and it just brings a whole level of complications. So I can see how there will be more regulation to this and I can also see how those platforms get more sophisticated with tracking those, with stopping those. And yeah, I feel that will be the future, but I also feel that. But at the same time, traders on the other side will also get more sophisticated. So it's a constant game of catching up. Yeah, cat and mouse. It never stops.

[Sarah Holder]

This is the Big Take from Bloomberg News. I'm Sarah Holder. To get more from the Big Take and unlimited access to all of bloomberg.com, subscribe [e-mail] podcastoffer if you like this episode, make sure to subscribe and review the Big Take. Wherever you listen to podcasts, it helps people find the show. Thanks for listening. We'll be back tomorrow.

[The Hartford Representative]

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