Easiest Money Ever: Bet Against Elon!

Summary

Bulwark Takes — “Easiest Money Ever: Bet Against Elon!” — Feb 26, 2026

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Main Theme

This episode dives into the explosion of prediction markets—like Kalshi and Polymarket—and how some sharp observers are making “easy money” by betting against outlandish predictions, especially those hyped by celebrity figures such as Elon Musk. The hosts explore a recent Wall Street Journal story about a tax expert who handily profited by betting against the idea that federal spending would decrease, fueled in part by Musk’s fans. They use this case as a springboard to discuss the broader realities, opportunities, and absurdities in the growing world of political and pop culture prediction betting.

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Key Discussion Points & Insights

The Wall Street Journal Story: Easy Money by Betting on Reality

• Alan Cole’s Bet:

  • Cole, a right-leaning tax analyst at the Tax Foundation, saw the promise of drastic federal spending cuts (as hyped by Musk) as nonsense. He bet his non-house savings on federal spending not decreasing—considering entitlement "mandatory" spending and inflation.
  • Sonny Bunch (02:57): “When Elon was like, yes, I’m going to come in and we’re going to slash … he was like, no, you’re not. That’s ridiculous. Nobody’s ever going to slash the spending … money always go up in federal government.”
  • The bet was basically: If federal spending in any quarter of 2025 is higher than in Q4 2024, you win.
  • The contract structure on the market (Kalshi) made this a “lock” due to how spending works.

• Notable Quote:

  • Ben Parker (04:38):
    “Even if [the government] spend[s] 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.”

Why More People Didn’t Take the Bet

• The panel is baffled: Even colleagues of Cole’s who recognized the lock didn’t put up the money.
• Sam Stein (05:22): “If you just happen to know about monetary policy, tax policy, anything like that, this was a lock. I’m surprised that more people didn’t do this.”

The Dynamics of Prediction Markets

• These markets are often swayed by hype and in-group thinking (e.g., Musk fans), creating price inefficiencies.

• Sonny Bunch (05:49):

  • “There was a huge asymmetry in it. That’s what’s so interesting about this to me, anyway.”
  • “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.”

• The lack of financial literacy and regulatory oversight on these platforms gives savvy insiders (or just people who paid attention in civics) a big advantage.

• Ben Parker (07:25):

  • “Or if you just paid attention in school, in civics class…”

Delight in Outsmarting the Hype Crowd

• The team relishes that someone who “paid attention in civics class” got the better of tech bros.
• Memorable Moment (07:34):
  • Ben quotes Cole’s wife reading forums and realizing the bet’s other participants simply didn’t understand the basics.

The Broader Prediction Market Ecosystem

• These platforms are expanding rapidly into all forms of speculation—sports, pop culture, and especially politics.
• Sam Stein (08:54): “They’re everywhere … how do you think it’s changing our politics?”
• Main concerns:
  • Increase in unregulated, possibly manipulation-prone speculation.
  • The emergence of “wisdom of the crowd” as a false substitute for real polling.

Wisdom of the Market: Myth or Reality?

• Sonny Bunch (11:08):
  • “The thing that drives me craziest is when people treat these as a substitute for actual polling … That drives me insane.”

Insider Trading & Enforcement Gaps

• Story of a Mr. Beast editor using insider info on Kalshi and being reported:
  • Sam Stein (13:25):
    • “We actually got a taste of that … an editor … suspended from the prediction market platform Kalshi and reported to federal regulators for insider trading … It’s the first time the company has publicly revealed … market manipulation.”
  • Enforcement is murky: These are private companies, not real financial regulators.
    • Sonny Bunch (14:24):
      • “Who they’re levying fines on their own platform. Like, how does that even …?”

Examples of “Dumb Money”

• The hosts review some of the silliest or lock bets on these markets:

  • Betting on what Jeff Probst will say on “Survivor.”
  • Wagering on specific Trump speech phrases.
  • Rotten Tomatoes scores (and how easily people could game them).
  • Whether Americans will get a “tariff stimulus check” (with complex fine print).
  • Will the U.S. confirm aliens exist before 2027? (Currently at 23 cents on the dollar.)

• Notable Quotes & Laugh Lines:

  • Sam Stein (16:20):
    • “Why is cookie 47% to say cookie? What the fuck? Why would he say Cookie?”
  • Ben Parker (17:10):
    • “Kelsey will come after you.” (on trying to game Rotten Tomatoes via prediction bets)
  • Sonny Bunch (17:52):
    • “I would never like Pete Rose. I would never bet against jvl. I would only bet on Sunny Bunch.”

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Notable Quotes & Memorable Moments

• Cole’s wife, on reading clueless posts (07:34):
  • “She read comments on the couch website from people on the other side of the bet and grew confident that they didn’t seem to understand what they were buying.”
• On market “wisdom,” from Bunch (11:08):
  • “That drives me insane because … I don’t think it … people are like, well, on polymarket this person has a 50% chance of winning … I’m just like, no, that’s not what this is saying at all.”
• On absurd market bets (16:20):
  • “Why is cookie 47% to say cookie? What the fuck? Why would he say Cookie?” — Sam Stein

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Timestamps for Key Segments

• [01:59] Episode Begins — Introduction, Wall St. Journal story setup
• [02:57] Alan Cole’s Big Bet — How and Why He Won
• [04:30] Breakdown of the Market Contract & Why It Was a “Lock”
• [05:22] Bafflement: Why Didn’t More People Take the Easy Money?
• [06:53] Market Asymmetry and “Elon Musk Addled Dorks”
• [07:25] Delight in Outsmarting the Tech Bros
• [08:54] The Rise of Prediction Market Betting in Politics
• [09:40] How the Odds Work, and Sonny’s Betting Tales
• [11:08] The Problem with Treating Markets as Polls
• [13:25] Insider Trading in Prediction Markets: The Mr. Beast Example
• [14:54] Silliest Bets & Gaming the System
• [16:20] Obsessing over Trinidadian Trump Speech Bets
• [18:00] More Bet Examples: Tariff Stimulus Check, Aliens
• [19:32] Adjudicating the Alien Disclosure Bet
• [20:11] Outro — Final Thoughts and Sign-off

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Tone & Atmosphere

• Smart-alecky and irreverent: The hosts combine genuine policy understanding with glee at puncturing hype, especially when tech optimism smashes into institutional reality.
• Full of in-jokes, light cynicism toward the “wisdom of markets,” and a palpable joy in being both policy-savvy and skeptical of new trends.

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This summary covers all substantive content, skipping pre-roll ads and closing promotions. For a full dose of Bulwark commentary on betting, celebrity hype cycles, and the pitfalls of prediction markets, this episode’s a rollicking listen.

Transcript

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[Sam Stein]

N 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. Ki 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 Sunny 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?

[Sonny Bunch]

More or less, yeah. I mean, Alan. Alan Cole's a guy who works at the Tax Foundation, Right of center organization. It's not like he's, you know, radical lib like us at the Bulwark, right? He's, he's doing. He's doing. He's doing, you know, you know, 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 was. We wasn't going to be homeless if he, if he lost this. 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 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, he still would have won. He still would have been in the, in the black.

[Sam Stein]

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, the grids. If federal spending in each quarter of 2025 exceeded federal spending in the fourth quarter of 2020, 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.

[Sonny Bunch]

And Ben, 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.

[Ben Parker]

Okay, a few details here that are important. One, as you pointed out, Sonny, this is mandatory spending, right? Which include 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 things. And, 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 put like a home equity loan and put that into the. Yeah, he should have put the house. That was a big mistake. Like, he should have bet more everything. Diamond hands to the moon on federal spending, on mandatory spending also.

[Sam Stein]

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 lot. 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 Bunch]

Sunny, 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, the, 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 calcium polymarket. Right? Like, those people are like, yes, of course Elon will lower the spending. He's, he's going to doge it, he's going to use the AI and they're going to come in, they're going to find all the extra spending, they're 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 Kalshee, 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.

[Sam Stein]

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've 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.

[Ben Parker]

Yeah, a little bit. Or if you just paid attention in school, in civics class. Can I read you this? Can I read you this one quote from the Beats?

[Sam Stein]

Because this is just.

[Ben Parker]

This is so great. He had. So the part of the part of the article is 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 couch website from people on the other side of the bed and grew confident that they didn't seem to understand what they were buying. That's it. It's like there is. There is a delicious part of this which is like the guy who did pay attention at civics class and in his PolySci class got one over on like, kind of the tech bros, the learn to code crowd, which I just savor in my soul.

[Sonny Bunch]

I mean, that is. That is like Ben's dream. That is. He's like, they're gonna make a move. They're gonna make a moneyball about me

[Sam Stein]

one day and it's gonna be Moneyball also. We'll put the pictures up. Let's. Hopefully, the pictures the Journal uses of Alan Coe are absolutely fantastic. It's like this dude just sitting back. He's clearly a, you know, a think tanker and he's got a. What is a glass of scotch or something on the front picture. It's like, sure.

[Ben Parker]

He's got. He's got a tumbler with like, the constitution, like we the people, like, engraved on it.

[Sam Stein]

The other one is, I think, another one. He's 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 DC art you could possibly.

[Sonny Bunch]

As we all do. Come on, you don't, you're telling. It's after 5pm oh yeah, we're informal wear. Sam, what are we.

[Sam Stein]

Let's talk about Kalshi in, in the, and in the predictive markets and in the how they're being adopted in politics writ large. Because they're everywhere. And for full disclosure, Sarah discussed this on, on, on the live stream last night. I mean that, you know, we have people who, from, from that world trying to advertise in the bulwark. We've said no, but they're everywhere. Like, I don't know if you guys saw it, but Nick Shirley, the right wing provocateur, video investigative journalist, he's not 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? Fed all sunny.

[Sonny Bunch]

Well, I don't, I don't know. I mean it's, it's interesting because I was, I was flipping around the, the politics contracts and I was kind of curious, particularly the ones in Texas. Right. I, you know, I live in Texas, so I'm paying some attention to the Democratic Senate primary here. And right now James Talrico is I think 80, 80% to win, which strikes me as very high. That is, Yeah, I 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 team. Cause I went to University of Virginia. I was like, oh, maybe, you know, they're probably pretty decent odds. And 50 to 1, it was 50 to 1 odds. I was like, oh, that's not bad. I was like, wait a second. Went to FanDuel. FanDuel had it for like 72 to 1. 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, 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 a, it's. How is it. But how is it affecting politics? I, I think it. The thing that drives me craziest is when people treat these as a substitute for actual polling.

[Sam Stein]

Right.

[Sonny Bunch]

That drives me insane because I don't think, I don't think it. I, you know, people are like, well, on poly market, this, this person has a 50% chance of winning the primary. I'm just like, no, that's not what this is saying at all. You're betting against.

[Sam Stein]

Well, it's the whole wisdom of the markets. But basically it can flip and you know, with one piece of information. So there's not really any wisdom at all. Bulwark Takes is sponsored by Soul. I've been more mindful about eliminating anything that is affecting my health habits like my workouts, sleep, bedtime routines and energy. So I've cut back on the evening glass of wine and instead I'm reaching for Soul's out of office gummies. They give me a light happy buzz without the calories of the next day drag because I don't need my parenting skills dragged down. Soul makes feeling good simple. They make delicious hemp derived CBD and THC products with precise dosing, clean ingredients and formulations designed for predictable feel good effects. Soul is the alcohol alternative that puts you in control of your mood. Their best selling out of office gummies deliver a customizable calming buzz for a 1.5mg microdose. That's for a gentle lift or the 15mg deeper, more elevated experience cautionary tale there. It's the easiest way to unwind without the grogginess or next day regret of alcohol. Give yourself the gift of a healthier unwind. Right now, Sol is offering our audience 30% off your entire order. 30%. Amazing. Go to getold.com and use the code BULL WORK TAKES. That's getold.com promo code BULL WORK TAKES for 30% off. Fact check for you currently on call sheet. James TALARIKO 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 Sriko was 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.

[Sonny Bunch]

Yeah, I would not, I would not bet on either of them.

[Ben Parker]

I could have sworn. There was a brief moment after the 2020 election when I think predict it had Donald Trump favored to be the next president after the election just because there were a bunch of Trump super fans in there dumping all their money. Buy Trump.

[Sam Stein]

Buy Trump. It's bad. I think it's creating bad incentives to trying 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 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. Cost officials said on Monday. It's the the first time the company has publicly revealed the results of an investigation into market manipulation on the popular app. Mr. Beast employee who Kashi identified as I'm not going to name the person traded around $4,000 on markets related to the streamer, the company said. Kalsha 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.

[Sonny Bunch]

As I said to you guys before we started, who they're levying fines on their own platform. Like, how does that even. How does that even.

[Ben Parker]

Yeah, Sonny, when you go to Vegas and you count cards in the casino,

[Sam Stein]

they take care of.

[Ben Parker]

It's not like they call the cops on you. It's the casino that takes care of it.

[Sonny Bunch]

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. I would not recommend it.

[Sam Stein]

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, can you go through some of your findings, please?

[Sonny Bunch]

Again, I'm really, really, really bad at these things. I can't, I can't tell you what will, what will happen or won't happen on, 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 $0.10. Yes, I will do that. That's. That's me. So I'm. I'm very. I'm very bad at this, but I do love. Our producer Matt pulled this, a wonderful one up about Survivor. Survivor. The Survivor premiere. What will Jeff Probst say During Survivor episode one? Will he say the word alliance? Will he say Mr. Beast or trust? Why are people betting on these things? I don't understand it.

[Sam Stein]

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, like, 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 he say 50,000?

[Ben Parker]

The Dow crossed 50,000, briefly.

[Sam Stein]

Oh, yeah. Dow 50,000. Okay. Drill, baby, drill. 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.

[Ben Parker]

I got to wonder, why is cookie at 47?

[Sam Stein]

Why is cookie 47% to say cookie? What the fuck? Why would he say Cookie?

[Sonny Bunch]

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. The problem with me is that I look at things like, I'm like, okay, will. Will. So there's. 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, you know, impact the. The. 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%.

[Sam Stein]

Then what's to prevent you from, like, trying to just game the Rotten Tomato scores?

[Ben Parker]

Kelsey will come after you.

[Sonny Bunch]

Yeah.

[Sam Stein]

Kashi's enforcement mechanisms will find you set

[Sonny Bunch]

up bots to do the. The audience one. No, I was saying before. Before this started. I was saying that we should be doing this at the. The Bulwark. Maybe. You know, how many likes will the next JBL post get? And we. If we know it's like a, you know, Trump in Minneapolis. That's going to be. 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, like, we know ahead of time what it's going to be. We got to bet on this. We got it. We got to start making. We got to start making a little bit of side revenue here. Sam, come on.

[Sam Stein]

Are you basically saying he's going long?

[Sonny Bunch]

No, no, I'm. No, I'm betting on the triads. I would never like Pete Rose. I would never bet against jvl. I would only bet on Sunny Bunch.

[Sam Stein]

There is one thing that Alan Co probably is looking at, which, which piqued my interest, which is because it's right in 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.

[Ben Parker]

Wait, 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 $1,000 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.

[Sam Stein]

So maybe you should take the bet because it's only 24% before 2027. Would you take that bet?

[Sonny Bunch]

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 US confirm that aliens exist before 2027? Here. 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 $0.23. Now, here's the thing. What if somebody just comes out and says, yes, we found microbes on Mars. Does that count? Yeah, I think that.

[Sam Stein]

Who adjudicates this?

[Ben Parker]

Does it count as definitively if it's

[Sam Stein]

RFP who adjudicates whether the actual announcement is sufficient to, you know, collect the

[Sonny Bunch]

bet outcome verified from White House. I don't know what that means. I don't know. I don't know. Who do they. There must be like a couchy person at the White House is like, yes,

[Sam Stein]

this one is yes, exactly.

[Sonny Bunch]

No, this one is no.

[Sam Stein]

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. 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.

[Ben Parker]

Maybe he's in those files, too.

[Sam Stein]

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.