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TRANSCRIPT
Jane Coaston: It’s Friday, April 10th, I’m Jane Coaston, and this is What a Day, the show that would never buy Yerba Mate from President Donald Trump’s youngest son. That’s despite news that Barron Trump is now one of five directors of a company that will soon be selling the caffeinated beverage to the people who buy anything else a Trump would sell them. [music break] On today’s show, the White House denies reports of a schism between the Trump administration and the Vatican, and Democrats are letting the F-bombs fly all over Twitter. They swear it’s a good idea. But let’s start with the war in Iran and how some people are making a lot of money betting on it. The Wall Street Journal reported on Thursday that the White House has forbidden staffers from betting on the war in prediction markets, and for good reason. From the moment the U.S. and Israel launch strikes in February, quite a few people have been profiting from them. That’s because they’ve been placing extremely well-timed bets on the website Polymarket, with some winning hundreds of thousands of dollars. Here’s [indistinct] back in March.
[clip of unknown news reporter] More than a dozen anonymous accounts placed bets predicting that the United States would strike Iran by Saturday the 28th of February. Most of those wages were placed in the hours before the first bombs fell. And many of the accounts had been created only days earlier.
Jane Coaston: Funnily enough, those extremely well-timed bets on action in Iran have been happening for a while now. CNN reported on one trader making nearly $1 million since 2024 by accurately predicting events in the ongoing conflict between the US, Israel, and Iran. And just this week, a group of newly created accounts bet correctly on the US and Iran reaching a ceasefire on April 7th. What are the odds? Polymarket and its main competitor, Kalshi, are massive businesses and they’re both aware that insider trading is a massive problem. In February, Israeli officials arrested multiple Israeli reservists and a civilian who were using classified information to place bets on the country’s military operations, using, you guessed it, Polymarket. So for more on how prediction markets are capitalizing on war, I spoke to Saahil Desai. He’s a senior editor at The Atlantic who recently wrote a piece about these so-called war markets. Saahil, welcome to What a Day!
Saahil Desai: Thanks for having me.
Jane Coaston: We have seen a huge increase in people betting on the Iran war. And what’s interesting to me is that they’re doing so correctly. Three accounts on Polymarket pocketed more than $600,000 betting on the ceasefire. And that’s after a single account won another $600,000 on the initial strikes on Iran. What do we know about these bets, and more specifically, who these bettors are?
Saahil Desai: So the short answer and the most troubling part of this, to me, is that we know nothing. So on Polymarket, um basically all bets happen through crypto, which essentially means that there’s a lot of anonymity under these bets. But based on the suspicious timing of these bets and the fact that, frankly, this happens over and over again in geopolitics, especially this year, you know, we’ve seen this during the Venezuela raid, we saw this when the bombs first hit Iran. We can’t say for sure that it’s insider trading, but at some point, you know, when there’s smoke, there’s fire, frankly. It seems like something suspicious is certainly going on, even though we can’t say that with certainty.
Jane Coaston: Now, I want to back up for a second. We’ve talked about prediction markets on the show, but can you remind us how they theoretically differ from traditional betting and when they really started to take off in popularity? What’s the difference here between this and like gambling?
Saahil Desai: You used the word theoretically, which I think is actually a really useful uh word it’s a word to keep in mind here, because these sites uh say that they are not gambling. They say that their a type of investing, right? So you know you put your money in the stock exchange or whatever, and they claim that betting on war or betting on anything else is akin to that. You are betting on the outcome of a future event, um and you know you’re not gambling in the sense that there’s no house you are betting against. In my opinion, I think that’s sort of a risible argument. Um. I think this is essentially gambling. If you even look at the advertising that these prediction markets run on social media, they often talk about this as gambling. So for all intents and purposes, like it’s the same as betting.
Jane Coaston: So when did we first see people hitting the metaphorical jackpot on events in the Iran war that to most people were a massive surprise?
Saahil Desai: Yeah, we saw that happening really like right before the um the bombs first hit, right? So there were lots of shady bets in the in the hours before the the Ayatollah was was assassinated. Um. And, you know, there was a New York Times analysis uh that I thought was quite telling where, you know, people were betting about when uh the US might evade Iran or enact missile strikes in Iran, but but in the hours leading up to the actual military campaign, there was a huge spike in the size of bets and the number of betters who were placing wagers on it. And so, you know, of course, that just suggests that people who had some inside information were using that to frankly just make a quick buck.
Jane Coaston: So we’ve seen at least one example in Israel of people with confidential information, members of the Israeli military, the Israeli reserves, who were placing bets on Polymarket using confidential information and were arrested. So if these bets are being placed by people with confidential information, are there ways to identify them? You’ve made the point that they’re using cryptocurrency which is untraceable. But would there be a way to track these people down anyway?
Saahil Desai: The short answer is probably not, frankly. Like for most cases, say say you’re some military reservist in the US who happens to have information about a strike. Uh you know if you’re in the Pentagon using the Pentagon’s internet, they’re probably going to find out what’s happening.
Jane Coaston: Probably.
Saahil Desai: If you’re you know I would hope so at least. But you know if you’re at home and for whatever reason, you know you’re someone who just has information and you’re you know you’re using a VPN or a virtual private network to sort of access Polymarket. Uh. It’s really hard to to to trace that. And there’s a reason that we really haven’t seen, you know, investigations really lead anywhere into this because it’s just like dead ends everywhere.
Jane Coaston: Now insider trading is illegal and Polymarket has tried to shut it down. They’ve repeatedly said that you cannot bet using classified information. Obviously people keep doing it, but I have to imagine that there are other concerns with the idea that people with knowledge of sensitive situations are putting money on them shortly before they happen as in they are influencing those events. What other issues could arise from these bets?
Saahil Desai: Yeah, I think that there’s a big difference between the things that people can bet on on prediction markets, such as, for example, people are betting um on you know what Mr. Beast will say in his next YouTube video. In fact, an editor on Mr. Beast got fired for insider trading uh on using Kalshi for that. But there’s there’s a distinction between, you know, betting on YouTube videos and betting on war, right? Like the fact that there could be insider trading happening here could materially be a problem for military campaigns going forward, right? There are lots of tools that can now spot potential insider trading, basically, in real time. Um and you know it’s not hard for any military in the world to get access to these types of tools and to sort of try and figure out and decipher a military strike before it happens.
Jane Coaston: I’m curious where we go from here, because I’ll say it, this sounds like gambling. And in Las Vegas, in the casinos, they do a ton of work to fight against the equivalent of insider trading, as in people getting information and trying to use it to make bets. So what would enforcement or regulation or even that same type of internal security look like on a platform designed for privacy like Polymarket.
Saahil Desai: Yeah, so I think that there’s like, there’s a big difference here between Polymarket and Kalshi. So Kalshi, the other big prediction market, is a regulated exchange. And so it has to um abide by what’s called KYC or Know Your Customer Regulations, um just as any other bank would. Um. Polymarket does not have that. In fact, Polymarket’s main platform, really, you can’t technically use it to gamble in the US. So what’s really tricky here is that there’s not a great answer on how to stop this, um, especially since frankly, the Trump administration has effectively given carte blanche to, uh, to Polymarket and, and Kalshi, you know, Trump Jr. is an advisor to both companies. Um, you know the Biden administration was actually regulating, um Polymarket in particular, quite stringently, and then, you know, Trump came into office and it was a different story. So it’s really hard to see. Uh. It’s hard to see a future in which this doesn’t just keep happening again and again and again.
Jane Coaston: What are you going to be looking for as whatever is taking place in Iran keeps happening and as these platforms get bigger and bigger already we’ve seen massive valuations for both Polymarket and Kalshi. You’ve made the point that they’re different, but they’re very wealthy companies. What should we be looking for?
Saahil Desai: I think what’s particularly concerning to me, apart from the war of it all, is what this all looks like as we careen towards the midterms. We frankly haven’t had an election yet in which prediction markets were this big, right? These platformings existed in 2024, but they were a fraction of the size that they are now. I don’t think we’re ready for what this could look like in which, you know, you could see congressional candidates placing money on themselves. You know, we’ve seen instances of that happening already. Um. But, you know, 2026, the midterms are poised to be the first prediction market election, and uh that’s about to pose about a thousand different strange scenarios that no one is ready to deal with.
Jane Coaston: I am not ready for any of that. Saahil, thank you so much for joining me.
Saahil Desai: Thanks for having me.
Jane Coaston: That was my conversation with Saahil Desai, senior editor at The Atlantic. We’ll link to his piece in the show notes. I’ll bet you know what I’m going to say. And if you were going to put some money on it, please don’t. You’d probably be right. We’ll get to more of the news in a moment. But if you like the show, make sure to subscribe, leave a five-star review on Spotify and Apple podcasts, watch us on YouTube, and tell your friends to gamble on us. But again, not really, just in the pun way. More to come after some ads. [music break]
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Jane Coaston: Here’s what else we’re following today. Headlines. Joining me is Crooked’s Washington correspondent, Matt Berg, to talk about the big stories. Hey Matt.
Matt Berg: Hey Jane.
Jane Coaston: Matt, Vice President J.D. Vance has built his entire political career on performing the appearance of good Catholic convert, but following reporting that a top Pentagon official got into a beef with the Vatican’s former ambassador to the U.S., Vance played dumb.
[clip of Vice President J.D. Vance] With no disrespect to the Cardinal, I don’t know who Cardinal Christophe Pierre is.
[clip of unknown news journalist] He’s the uh ambassador to the [?] in the US.
[clip of Vice President J.D. Vance] Oh okay, okay, I do I’ve met him before sorry. I just didn’t remember the name. I’ve never seen this reporting. I’d like to actually talk to Cardinal Christophe Pierre.
Jane Coaston: I don’t believe for one second that this man, whose upcoming book is literally titled Communion, Finding My Way Back to Faith, forgot who the Vatican’s former U.S. ambassador is. But whatever. The Trump administration is trying to pretend like it’s not beefing with the Vatican, following reports that Elbridge Colby, the Pentagon’s policy chief, tried to bully Cardinal Pierre into supporting US foreign policy.
Matt Berg: That’s right. This all stems from a report that Colby met with Pierre in January and basically told Pierre that the Catholic Church would be smart to support U.S. Foreign policy despite everything Trump has done. The Defense Department on Thursday tried swatting down the drama on social media, calling the meeting, quote, “substantive, respectful and professional,” alongside a few photos of Colby and Pierre shaking hands to make it all seem like it was just a good little hangout. The US MC to the [?] also chimed in saying that Pierre, quote, “emphatically denied the media’s portrayal of his meeting.”.
Jane Coaston: So convincing. The Vatican was reportedly so alarmed by news of the meeting that Pope Leo scrapped his plans to travel to the United States this year. The Pope is opting for a virtual appearance instead. The White House also says this is no big deal, right?
Matt Berg: Exactly. White House spokeswoman Anna Kelly told me on Thursday that the Trump administration’s relationship with the Vatican is, quote, “positive.”
Jane Coaston: Look I’m a Christian. I believe that Jesus Christ died and rose from the dead. I believe a lot of things. I absolutely do not believe that the Trump administration’s relationship with the Vatican is positive. Because why would it be? What exactly about this administration has demonstrated any adherence to Catholic norms, which are not, as I recall, own the libs? But here’s the thing. The Catholic Church has roughly 1.4 billion members around the world. It has been around for centuries. MAGA’s been around for what? Eleven years? And no one can really say what it is except for whatever Trump says it is? If the church can outlast multiple schisms, at least one murderer pope, a few murdered popes, and more wars than I can count on two hands, I think it’s betting it can outlast a presidential administration full of dorks.
Matt Berg: I think you’re totally right, Jane.
Jane Coaston: And speaking of Trump’s disastrous foreign policy, the US-brokered ceasefire plan in the Gaza Strip that went into effect last fall is failing, according to an analysis released on Thursday by five humanitarian groups, including Oxfam and Refugees International. The report details how Palestinians are still going to bed hungry, have to deal with long lines for clean water, and are dying of diseases because of the decimated health care system.
Matt Berg: Right. Some humanitarian workers say that Israel is still bombing Gaza as well. Here’s a clip of Dr. Tanya Haj-Hassan, a pediatric intensive care physician who has worked extensively in Gaza. She spoke on a panel with a few other humanitarian workers on Thursday to discuss these reports.
[clip of Dr. Tanya Haj-Hassan] There is absolutely no ceasefire. I was last in Gaza in February. Um. I left, I think it was February 19th. And from the moment I arrived, there was constant bombardment that first night, the following day, I started asking colleagues what was going on and they said, oh, it’s been like this ever since the ceasefire.
Matt Berg: And you might remember that in January, Trump’s special envoy, Steve Witkoff said that the second phase of the ceasefire was set to go into effect. But the Iran war has taken the attention away from that. And Dr. Hassan said that reconstruction has not started yet.
Jane Coaston: Matt, isn’t Trump’s Board of Peace supposed to help rebuild Gaza?
Matt Berg: That’s the intention. It’s unclear if that has actually been followed through in any way yet. I spoke with Rob Malley, who was Biden’s special envoy to Iran recently. And he’s been you know talking with people who are involved in this and said that nothing has started so far as far as reconstruction is concerned. But it’s no secret that pretty much everything Trump has been doing, foreign policy or domestic, has been making Democrats angry. And they’re so angry that they’re literally saying, Fuck this. The language situation has gotten so extreme that the New York Times analyzed which Democrats have been saying the word fuck most frequently.
Jane Coaston: And the winner is [ding] Arizona Democratic Senator Ruben Gallego, with at least 77 tweets from 2020 through the end of March 2026 using the expletive. Fun fact, no one was even close to Gallego. Wisconsin Republican Representative Derek Van Orden came in second with a meager 35 posts.
Matt Berg: Boo. I mean, Democrats get a lot of hate for, you know, seeming performative when they swear, but Gallego has been on this trend way before it was cool apparently. But I mean what do you think? Is saying bad words a secret sauce for all of Democrats’ struggles over the years?
Jane Coaston: I mean if they mean it, fuck it. Like, why not try that? As always, thank you so much for hanging out, Matt.
Matt Berg: Thanks for having me.
Jane Coaston: And that’s the news. [music break] That’s all for today. If you liked the show, make sure you subscribe, leave a review, don’t let an AI powered robot care for your elderly loved ones, and tell your friends to listen. And if you’re into reading, and not just about Abby, a companion robot which is described by the Washington Post as, quote, “very personable and sassy and could soon be coming to nursing homes and retirement communities,” like me, What a Day is also a nightly newsletter. Check it out and subscribe at Crooked.com/subscribe. I’m Jane Coaston. And Abby reportedly leads group activities like Tai Chi, but really excels at one-on-one interactions. But again, Abby is a robot, so go visit your grandma. [music break] What a Day is a production of Crooked Media. It’s recorded and mixed by Desmond Taylor. Our associate producer is Emily Fohr. Our producer is Caitlin Plummer. Our video editor is Joseph Dutra. Our video producer is Johanna Case. We had production help today from Greg Walters, Matt Berg, and Ethan Oberman. Our senior producer is Erica Morrison, and our senior vice president of news and politics is Adriene Hill. Our theme music is by Kyle Murdock and Jordan Cantor. We had help today from the Associated Press. Our production staff is proudly unionized with the Writers Guild of America East. [music break]
