Bulwark Takes

Easiest Money Ever: Bet Against Elon!

19 min
Feb 26, 2026about 2 months ago
Listen to Episode
Summary

The hosts discuss how a Tax Foundation analyst made a profitable bet against Elon Musk's spending reduction claims by wagering on federal spending increases through prediction markets like Kalshi. The episode explores how prediction markets are reshaping politics, the risks of unregulated betting platforms, and examples of absurd and manipulable markets.

Insights
  • Prediction markets on political outcomes are heavily influenced by ideological bias rather than informed analysis, creating exploitable asymmetries for those with domain expertise
  • Mandatory federal spending (Social Security, Medicare, Medicaid) combined with inflation makes certain bets mathematically guaranteed wins, yet most retail traders miss obvious opportunities
  • Prediction market platforms lack meaningful regulatory oversight, enabling insider trading and self-policing that creates moral hazard and market manipulation risks
  • The expansion of prediction markets into granular political and cultural outcomes (Trump speech phrases, Survivor dialogue) incentivizes speculation over informed betting
  • Information asymmetry favors policy experts and civics-literate bettors over tech-focused retail traders who dominate these platforms
Trends
Prediction markets rapidly expanding into politics, entertainment, and micro-events as mainstream betting alternativesUnregulated prediction platforms attracting influencer sponsorships and becoming culturally normalized among younger demographicsInsider trading and market manipulation emerging as systemic risks in decentralized prediction markets with weak enforcementPolicy experts and domain specialists exploiting retail trader overconfidence in prediction markets for guaranteed returnsSelf-regulation by prediction market platforms replacing government oversight, creating accountability gapsPrediction market odds being misinterpreted as polling data or political forecasts by mainstream media and analystsMicro-betting markets on trivial outcomes (speech phrases, TV show details) creating perverse incentives for manipulationTech industry figures and influencers using prediction markets as both investment vehicles and marketing platforms
Companies
Kalshi
Prediction market platform where Alan Cole made his federal spending bet; subject of insider trading investigation in...
Polymarket
Prediction market platform sponsoring influencers like Nick Shirley and Walter Bloomberg; discussed as unregulated be...
Shopify
E-commerce platform sponsor offering templates, AI tools, and inventory management for online businesses
Sol
Hemp-derived CBD and THC product company offering gummies as alcohol alternative; episode sponsor with promo code
Tax Foundation
Right-of-center think tank where Alan Cole works; organization that employs the analyst who profited from anti-Musk s...
The Bulwark
Political media outlet hosting the podcast; has declined prediction market advertising despite industry outreach
FanDuel
Sports betting platform mentioned for comparison of odds on University of Virginia basketball
MrBeast
YouTube creator whose editor was suspended from Kalshi for insider trading on markets related to the streamer
People
Alan Cole
Tax Foundation analyst who bet life savings against federal spending cuts, profiting from prediction market bet on ma...
Elon Musk
Central figure whose DOGE spending reduction claims were bet against; subject of prediction market speculation by ret...
Sam Stein
Managing editor at The Bulwark; host of the episode discussing prediction markets and federal spending bets
Ben Parker
Co-host discussing prediction market dynamics, insider trading risks, and examples of absurd betting markets
Sonny Bunch
Co-host providing analysis of prediction markets, federal spending mechanics, and retail trader behavior on platforms
James Tallarico
Texas Democratic Senate primary candidate with 71% odds on Kalshi; also listed at 3% for 2028 Democratic presidential...
Jasmine Crockett
Texas Democratic Senate primary candidate with 31% odds on Kalshi despite leading in some traditional polls
Donald Trump
Subject of multiple prediction markets including speech phrase betting and 2028 presidential odds; declassification p...
Nick Shirley
Right-wing provocateur and video journalist sponsored by Polymarket; wearing branded merchandise for prediction marke...
Walter Bloomberg
Infamous Twitter account posting sponsored content for Polymarket prediction market platform
RFK
Mentioned in context of potential alien disclosure announcements and adjudication of prediction market outcomes
Jeff Probst
Survivor host subject of prediction market betting on whether he will say specific words during episode premiere
LeBron James
Listed at 1% odds for 2028 Democratic presidential nomination on Kalshi prediction market
Quotes
"Money always go up in federal government. Like money, money always go up, never go down."
Sonny Bunch
"She read comments on the Cal Street website from people on the other side of the bet and grew confident that they didn't seem to understand what they were buying."
Sam Stein
"The guy who did pay attention in civics class and in his poly psych class got one over on the tech bros, the learn to code crowd, which I just savor in my soul."
Sam Stein
"This is the genius of Alan Cole... he saw this and was like, wait, this doesn't make any sense. I know this better than these people do, obviously."
Sonny Bunch
"Fuck around, find out."
Kyle Sheehan (Kalshi CEO, quoted)
Full Transcript
Starting a business can be overwhelming. You're juggling multiple roles, designer, marketer, logistics manager, all while bringing your vision to life. Shopify helps millions of business sell online. Build fast with templates and AI descriptions and photos, inventory and shipping. Sign up for your one euro per month trial and start selling today at shopify.nl. That's shopify.nl. It's time to see what you can accomplish with Shopify by your side. Hey, everybody. It's me, Sam Stein, managing editor at The Bulwark. I'm joined by Ben Parker and Sonny Bunch. We're here to talk about gambling, Kalshi, Elon Musk, how to make easy money, how to make dumb money. Guys, thanks for doing this. So what sparked our interest this morning was a Wall Street Journal piece, which was kind of amazing in a way. Basically, I'm going to try to summarize it, but Sonny will do the full scope of it. Some guy, some tax nerd here in Washington, D.C., really understood that Elon Musk was a fraud when he started Doge and that the money we spend will not go down because we have these things called entitlement programs that the federal government has to spend money on and they grow bigger and bigger. And Elon Musk wasn't going to touch it. And so he put his entire life savings into the prediction markets saying that we will not, in fact, spend less money at the end of the year. And lo and behold, he was a big winner. Sonny, did I get that right? More or less. Yeah. I mean, Alan Cole's a guy who works at the Tax Foundation, right of center organization. It's not like he's a radical lib like us at the Bulwark, right? He's doing kind of right of center tax stuff. And when Elon was like, yes, I'm going to come in and we're going to slash, we're going to get rid of all the fraud. We're going to slash the spending. He was like, no, you're not. That's ridiculous. Nobody, nobody's ever going to slash the spending. That's never going to happen. And so he, he pulled all of his money out of, you know, the regular stocks and put it in this. He did not, he made it very clear. He did not literally bet the house. The equity stayed in the house and he, you know, so it wasn't, we wasn't going to be homeless if he, if he lost us, but, you know, I'm sure, I'm sure he really had to have a good chat with his wife. Like, look, this is what you have to understand is money always go up in federal government. Like money, money always go up, never go down. And so I can't possibly lose. And sure enough, he was right. He even, he even hedged the bets in such a way that like, even if there was a $50 billion reduction in spending, which again, possible, uh, he still would have won. He still would have been in the, in the black. Yeah. What were the actual contours of the bet? It was that the, I'm just trying to make sure I understand this. If federal spending, if federal spending in each quarter of 2025 exceeded federal spending in the fourth quarter of 2024, he wins. So that's the bet. It's like each quarter has to be a little bit higher than it was in the fourth quarter of 2024. And Ben, you made the point, you made the point in Slack that whoever wrote this did a terrible job. Whoever wrote the contract for this did a terrible job. Because, okay, a few details here that are important. One, As you pointed out, Sonny, this is mandatory spending, right, which includes Social Security, Medicare, Medicaid, things Donald Trump ran on not touching, things that were never going to be touched, things that like even if Congress passed a law, they're not they have to spend anyway. And it's in nominal dollars. So even if they spend exactly the same real amount, they have to spend more money because there's a little bit of inflation all the time. Like this is a lock. The fact that this guy didn't get a home equity loan and put that into the – yeah, he should have bet the house. That was a stake in the stake. He should have bet more. Everything. Diamond hands to the moon on federal spending, on mandatory spending. Also, the other thing is that even if they had gone after Social Security and Medicare, they weren't going to do it in a way that would cut it immediately. It was always going to be sort of like down the road we will do these types of reductions. It would have been a ramp up. So if you just happen to know about monetary policy, tax policy, anything like that, this was a luck. I'm surprised that more people didn't do this. Like he was advised by colleagues to do this. Why didn't they also put their money where their mouth is, Sonny? Set aside the experts, set aside the people who actually follow this and understand, again, money always go up. Like, set those people aside. The fact of these markets is, and the fact of this market in particular, especially when somebody like Elon Musk is involved, who is very much a figure of adoration amongst the sort of person who is attracted to Calci and Polymarket, right? Like, those people are like, yes, of course Elon will lower the spending. He's going to doge it. He going to use the AI and they going to come in They going to find all the extra spending They going to find the fraud because the private sector is so good at these things You know the government is wasteful and terrible Elon Musk is very smart and has these great systems And so he's going to come in and change it. So he wasn't even really betting against he wasn't betting against Calci, but he also just wasn't even betting against the actual funding. Right. He was what he did was he saw a market where all of these Elon Musk addled dorks were like, yes, of course, he's going to do it and took advantage of it. There was a huge asymmetry in it. That's what's so interesting about this to me anyway. Well, that and Ben, the other thing is that there's like this whole – I mean I'm sure there's insider trading happening on these platforms because they're completely unregulated. But Sunny's got a good point, which is that because these platforms are expanding into fields so rapidly, including politics, people who just sort of know the system and how it works are going to stand to have a much better advantage than casuals who have just come on board and decided, oh, yeah, we're obviously going to be going to war with Iran by Friday, right? Like you can basically read the tea leaves much better if you've actually been around the block. Yeah, a little bit. Or if you just paid attention in school, in civics class. Can I read you this one quote from the piece? This is so great. So part of the article in the Wall Street Journal is about how Cole had to convince his wife to go along with this bet of other life savings. She read comments on the Cal Street website from people on the other side of the bet and grew confident that they didn't seem to understand what they were buying. That's it. There is a delicious part of this, which is the guy who did pay attention in civics class and in his poly psych class got one over on the tech bros, the learn to code crowd, which I just savor in my soul. That is like Ben's dream. He's like, they're going to make a money ball about me one day. There is some money ball about me. I got it. Also, we'll put the pictures up. Let's hopefully put it. The pictures the journal uses of Alan Co. are absolutely fantastic. It's like this dude just sitting back. He's clearly a think tanker, and he's got a glass of scotch or something on the front picture. Sure. He's got a Tumblr with the Constitution, like we the people, engraved on it. The other one is – I think another one is in a black tie tux just on his couch checking his phone with the sunlight draped on him. It's amazing. It's the most DCR you could possibly. As we all do. Come on. You're telling – after 5 p.m., we're informaware, Sam. What are we? Let's talk about Calci and the predictive markets and how they're being adopted in politics writ large because they're everywhere. And for full disclosure, Sarah discussed this on the live stream last night. I mean, we have people from that world trying to advertise on the Bulwark. We've said no. But they're everywhere. I don't know if you guys saw it, but Nick Shirley, the right-wing provocateur video investigative journalist, he's now going around wearing a Polymarket hoodie sweater because he's sponsored by Polymarket. There's this guy, Walter Bloomberg, some infamous Twitter account, who is putting up posts that he said are sponsored by Polymarket. So it's everywhere, this stuff. How do you think it's changing our politics at all summer? Well, I don't know. I mean, it's interesting because I was flipping around the politics contracts, and I was kind of curious, particularly the ones in Texas, right? I live in Texas, so I'm paying some attention to the Democratic Senate primary here. And right now, James Tallarico is, I think, 80% to win, which strikes me as very high. Is that true? That's insane. That is, yeah, like 80 cents on the dollar, which I, like, if I was a gambling person and I'm not, I'm terrible. Quick story about how terrible I am at this. I just went to look and see how how what the odds are on Virginia men's basketball teams. I went to University of Virginia. I was like, oh, maybe, you know, they're probably pretty decent odds in 50 to one. It was 50 to one odds. I was like, oh, that's not bad. That's like, wait a second. Went to FanDuel. FanDuel had it for like 72 to one. So I was like, I would have I would have been leaving money on the table if I want to make that bet. Anyway, the the the Crockett thing is really interesting to me because she is leading in many polls, not all of them. But she is like I I think she has a higher profile. I I think she she has at the very least as good a chance to win as he does. And she is a massive underdog. So that's the sort of thing I would be betting in. But I'm terrible at betting. So I don't do it. I don't do it. I don't do this at all. It's it's how is it? But how is it affecting politics? I think it the thing that drives me craziest is when people treat these as a substitute for actual polling. Right. That drives me insane because I don think I don think it I you know people are like well on poly market this this person has a 50 chance of winning the primary I just like no that not what this is saying at all You betting against what other people think Well it the whole wisdom of the markets It's going to happen. Basically, it can flip with one piece of information. So there's not really any wisdom at all. 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Give yourself the gift of a healthier unwind. Right now, Sol is offering our audience 30% off your entire order. 30%. Amazing. Go to GetSold.com and use the code BULWARKTAKES. That's GetSold.com promo code BULWARKTAKES for 30% off. Fact check for you. Currently on call sheet, James Tallarico has a 71% chance of winning to Jasmine Crockett's 31%. There was a poll this morning that had her up 56 to 44. So that's it. I will say there's also James Tallarico is mentioned in another bet. 2028 Democratic nominee for president. He's at 3% probability. LeBron James is at 1%. I don't like any of those odds. I would not bet on either of them. I could have sworn there was a brief moment after the 2020 election when I think predicted had Donald Trump favored to be the next president after the election. Just because there are a bunch of Trump super fans in there dumping all their money. Buy Trump. Buy Trump. It's bad. I think it's creating bad incentive structures too. And we did reference the insider trading sort of in passing. But I do think, I mean, there's going to be huge opportunities. There already are for people to just do insider trading on this stuff. We actually got a taste of that non-politics related. As we were prepping for this show, a story broke on NPR. Mr. Beast, editor suspended and reported for insider trading. It goes like this. An editor who works for YouTube's biggest creator, Mr. Beast, has been suspended from the prediction market platform Kalshi and reported to federal regulators for insider trading. Kyle Sheehan said on Monday, it's the first time the company has publicly revealed the results of an investigation into market manipulation on the popular app. Mr. Beast's employee, who Kyle Sheehan identified as, I'm not going to name the person, traded around $4,000 on markets related to the streamer, the company said. Kyle Sheehan then tweeted out, fuck around, find out, as if it's some sort of big regulatory body. But that's like, it did raise the question, like, who's actually regulating this? Just the company self-regulating, I suppose. As I said to you guys before we started, they're levying fines on their own platform? How does that even work? Yeah, Sonny, when you go to Vegas and you count cards in the casino, it's not like they call the cops on you. It's the casino that takes care of it. This did happen to me last time I was in Vegas with Sarah Longwell. I had a trip to the back room. It was not pleasant. All right, let's close up here by, I asked you, Sonny, to find some of the surest bets or the dumbest bets on Kalshi. Can you go through some of your findings, please? Again, I'm really, really, really bad at these things. I can't tell you what will happen or won't happen on anything. I'm the sort of guy who goes to these things and like, yes, one battle after another will win Best Picture. Okay, I'll bet $1 to win 10 cents. Yes, I will do that. That's me. So I'm very bad at this. But I do love our producer, Matt, pulled this wonderful one up about Survivor. Survivor, the Survivor premiere. What will Jeff Probst say during Survivor Episode 1? Will he say the word alliance? Will he say Mr. Beast? Why are people betting on these things? I don't understand it. I've seen videos of people watching Donald Trump speeches because they bet on him to say something. And they're just waiting and waiting. And then he utters it out and this pure joy comes over them. Because people are idiots and they live on the edge like that. There is one about what will Trump say this week. Sleepy Joe came in at 56%. Transgender, 59%. Some of the ones at 99% are 50,000. Why would you say 50,000? The Dow crossed 50,000 briefly. Oh, yeah. Dow 50,000. Okay Drill Baby Drill at 99 Hockey at 99 Melania 99 Nobel 99 all these are sure Somali 99 where are the deals I want some upside on these bets I gotta wonder why is cookie at 47 47% to say cookie what the fuck why would he say cookie I don't I don't know this and so this is this is the genius of Alan Cole if we can bring it back to the story here is because he saw this and was like, wait, this doesn't make any sense. I know this better than these people do, obviously. The problem with me is that I look at things like, I'm like, okay, so you can bet on Rotten Tomatoes scores. You can bet on Rotten Tomatoes scores. And obviously I can't do this. As a Rotten Tomatoes certified critic, I wouldn't want to improperly impact the ratings here. But you can bet, for instance, on whether or not Scream 7 will be above 55% or above 60%. or, let's see, let's see, what else? Or above 45%. Then what's to prevent you from, like, trying to just game the Rotten Tomatoes course? Kelsey will come after you. Yeah, Kelsey's enforcement mechanisms will find you. Set up bots to do the audience one. No, I was saying before this started, I was saying that we should be doing this at the, you know, the bulwark, maybe. You know, how many likes will the next JBL post get? And if we know it's like, you know, Trump in Minneapolis, list, that's going to be a big one. You take the over on that one. But if it's like electricity production in the Northwest from 1950 to 1970, that's low likes on that one. That's not going to be a banger. So we know ahead of time what it's going to be. We've got to bet on this. We've got to start making a little bit of side revenue here, Sam. Come on. Are you basically saying you're going to be shorting triads? No, I'm betting on the triads. I would never, like Pete Rose, I would never bet against JVL. I would only bet on it. There is one thing that Alan Cole probably is looking at, which piqued my interest, which is because it's right in his wheels. Will Americans receive a tariff stimulus check? And they have different odds before July, before August, before 2027. None of them have great odds. So probably wouldn't bet on them. But if they were to tick up, that's a surefire one. It's like, no, they're not going to get the checks. They will never come. Wait a minute. I looked into this one a little bit. Did you read the fine print? I looked into this one a little bit. It says at least 1 million Americans have to receive a check of at least a thousand dollars each that basically some part of the federal government says comes from tariff revenue which is which is i mean money's fungible right they can send out checks from some account and say like oh yeah this revenue came from tariffs instead of taxes because like who cares what's the difference so i don't know that one so maybe you should take Because it's only 24% before 2027. Would you take that bet? I don't know. That's not bad. That's not bad. No, my favorite one here, I sent this to you guys, is the aliens one. Will the U.S. confirm that aliens exist before 2027? Here are the rules. If the president, any member of the cabinet, any member of the Joint Chiefs of Staff, or any U.S. federal agency definitively states that extraterrestrial life or technology exists before January 1, 2027, the market resolves to yes, right? It's currently at 23 cents. Now, here's the thing. What if somebody just comes out and says, yes, we found microbes on Mars? Does that count? Yeah, who adjudicates this? Does it count as definitively if it's RFK? Who adjudicates whether the actual announcement is sufficient to, you know, collect the bet? Outcome verified from White House. I don't know what that means. I don't know. I don't know who. There must be like a Kalshi person at the White House is like, yes, this one is yes. Yeah, exactly. No, this one is no. I will say I'm on the page now. February 19th, the odds were 17.5%. February 20th, it went up to 27.7%. I believe that's right when Trump put out his post about declassifying all that shit. So the market moved, but now it's back down to 23%. I don't know why they don't think Trump's going to follow through on that one. Guys, this was fun. I don't know what else to say. Maybe he's in those files too. Yeah. Well played, Ben. All right. I think we could leave it there. If folks want to hear more betting content, subscribe to The Bulwark. We're going to do more of these. I'm probably not going to do any more of these. We do them occasionally. No one seems to really like this topic. We find it very funny. Ben, Sonny, thanks, guys. Really appreciate it. Starting a business can be overwhelming. You're juggling multiple roles, designer, marketer, logistics manager, all while bringing your vision to life. Shopify helps millions of business sell online. Build fast with templates and AI descriptions and photos, inventory and shipping Sign up for your 1 euro per month trial and start selling today at shopify.nl That's shopify.nl It's time to see what you can accomplish with Shopify by your side