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

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.

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.”

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

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

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.

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.