This week we talk about prediction markets, incentives, and gambling addiction.

We also discuss insider trading, spot-fixing, and Gatorade.

Recommended Book: The Kingdom, the Power, and the Glory by Tim Alberta

Transcript

Prediction markets are hundreds of years old, and have historically been used to determine the likelihood of something happening.

In 1503, for instance, there was a market to determine who would become the next pope, and from the earliest days of commercial markets, there were associated prediction markets that were used to gauge how folks thought a given business would do during an upcoming economic quarter.

The theory here is that while you can just ask people how well they think a political candidate will fare in an election or who they think will become the next pope, often their guesses, their assumptions, or their analysis will be swayed by things like political affiliation or maybe even what they think they’re meant to say—the popular papal candidate, for instance, or the non-obvious, asymmetric position on a big commercial enterprise that might help an analyst reinforce their brand as a contrarian.

If you introduce money into the equation, though, forcing people to put down real currency on their suspicions and predictions, and give them the chance to earn money if they get things right, that will sometimes nudge these markets away from those other incentives, making the markets commercial enterprises of their own. It can shift the bias away from posturing and toward monetization, and that in turn, in theory at least, should make prediction markets more accurate because people will try to align themselves with the actual, real-deal outcome, rather than the popular—with their social tribe, at least—or compellingly unpopular view.

This is the theory that underpins entities like Polymarket, Kalshi, Manifold Markets, and many other online prediction markets that have arisen over the past handful of years as regulations on these types of businesses have been eased, and as they’ve begun to establish themselves as credible players in the predicting-everything space.

In politics in particular, these markets have semi-regularly shown themselves to be better gauges of who will actually win elections than conventional polls and surveys, and though their records are far from perfect and still heavily biased in some cases, such community-driven predictions from money-motivated markets are gaining credibility because of their capacity to incentivize people to put their money where their mouths are, and to try to profit from accurate preordination.

The flip-side of these markets, and some might even say a built-in flaw with no obvious solution, is that they are rife with insider trading: people who are in the position to know things ahead of time making in some cases millions of dollars by placing big bets that, for them, aren’t bets at all, because they know what will or what is likely to happen.

This seems to have occurred at least a few times with big political events in 2025, and it’s anticipated that it could become an even bigger issue in the future, especially for markets that use cryptocurrencies to manage payments, as those are even less likely than their fiat currency peers to keeps solid tabs on who’s actually behind these bets, and thus who might be trading on knowledge that they’re not supposed to be trading on.

That said, it could be argued that such insider trading makes these markets even more accurate, eventually at least. And that points us toward another problem: the possibility that someone on the inside might look at a market and realize they can make a killing if they use their position, their power to sway these markets after placing a bet, giving them the ability to assure a payout by abusing their position—major events being influenced by the possibility of a community-funded payday for those in control.

What I’d like to talk about today is the same general principle as it’s playing out in the sports world, and why the huge sums of money that are now sloshing around in the sports betting industry in the US are beginning to worry basically everyone, except the sports betting companies themselves.

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In October of 2025, the head coach of the NBA basketball team, the Portland Trail Blazers, Chauncey Billups, Miami Heat player Terry Rozier, and former NBA player Damon Jones, and about 30 other people were arrested by the FBI due to their alleged illegal sports gambling activities. Rozier was already under investigation following unusual betting activity that was linked to his performance in a 2023 game—he was later cleared of wrongdoing, but the implication then and in this more recent instance is that he and those other folks who were rounded up by the FBI may have been involved in rigging things so they could get a big payoff on gambling markets.

Similar things have been happening across the sports world, including a lifetime ban for Jontay Porter, a former Toronto Raptors player, who apparently gave confidential information to people who were placing bets on NBA games—he later pleaded guilty to conspiracy to commit wire fraud as a result of that investigation—and in November of 2025 two Major League Baseball players, both of them pitchers for the Cleveland Guardians, Emmanuel Clase and Luis Ortiz, were charged by federal prosecutors for allegedly rigging pitches to benefit people betting on those pitches; they’ve been charged with wire fraud and money laundering, and each could face up to 65 years in prison.

And those are just a few of the many instances of game-rigging that have been alleged in recent years, the specifics of which vary, but the outcome is always to give someone an advantage in these markets, which are only recently broadly legal across the United States, and which thus allow folks with the right connections or some money to invest ahead of time to, for instance, pay a pitcher to throw an inning, or pay a coach to tell them who will be benched and when, so that they can make a big wager with less of a risk, or in some cases, no risk at all.

One of the big issues here is that rather than simply being a which-team-will-win sort of thing, many of these bets are highly specific and granular, including what are called proposition or prop bets that allow folks to gamble on the number of strikeouts a pitcher will tally in a given inning and other very specific things.

If a pitcher were to then place a bet, perhaps through an intermediary, on their own prop bet-related performance, they would stand a decent chance of tallying the right number of strikes and balls. They could also sell that information to someone else, taking a guaranteed payout in exchange for the foreknowledge they grant that gambler, who could then do what they want with the information, and then if they do well with it, they could pay that pitcher to do the same again in the future.

This type of bet is called spot-fixing, and it’s seen across prediction markets, not just sports markets. Pitchers can fix an inning of a game, but poker players can also go all-in or fold a given number of times in a tournament, and the folks in charge of dumping Gatorade over the winning coach following a Super Bowl event can leak that color, based on their foreknowledge of the setup, to gamblers—these markets are sprawling and varied, and anyone in any position of power who can make decisions about such things, or who’s involved enough to leak information can do so at a profit, either themselves putting down money on spot-fixed prop bets, or selling that information to those who will themselves place a bet.

The issue sports organizations in the US are now running into is that while they aligned themselves with sports gambling entities like DraftKings and FanDuel after these platforms were legalized in more states following the striking-down of a federal ban on such things in 2018—as I record this, they’re currently legal in 31 states, alongside Washington DC and Puerto Rico—and they’ve profited a fair bit from that, allowing these businesses to become sponsors, to slap their logos on everything, and to generally become interwoven with the leagues themselves; despite all that, they’ve also created a sports culture in which betting is ultra-common, and that means fans are no longer just fans, they’re putting down money on various possible sports-related outcomes.

That means folks who were maybe previously die-hard fans of their local team may no longer just be disappointed when their team loses, they’ll be financially impacted, perhaps even devastated. And many athletes who play on these teams, in these leagues, are now suffering all kinds of abuse and threats from people who decided to put a lot of money on their performance, but who failed to win a game, or maybe even throw the exact right number of strikes and balls in a given inning.

This points at two big issues with sports betting in the US right now.

First is that there’s a lot of money splashing around in this space. An estimated $160-170 billion was wagered by US citizens in 2025 alone, generating about $16.4 billion in revenue for sportsbooks—the entities that take these sorts of bets.

That’s likely a significant undercount, too, as more generalist prediction markets are also getting involved in the sports betting game, blending this type of gambling with other sorts of prediction markets, like those related to politics and international happenings, like war.

And second, a lot of people are gambling a lot of money on sports stuff right now, and that’s becoming an issue. In October of 2025, a Pew Research poll found that 43% of US adults think legalized sports betting is bad for society, up from 34% in 2...