This is a commentary piece. Dave Schilling’s argument in a Guardian opinion column is that the United States has stopped pretending to object to gambling in general and now objects only to the specific people who get caught — which is a description of enforcement by embarrassment, not regulation.

Two cases from the past two weeks carry his argument.

Santos and Simmons

Kalshi banned former congressman George Santos from its platform for life. He had bet on himself not to attend the State of the Union address, and then did not attend. He won more than $17,000, which he must now return, and faces more than $80,000 in total fines from Kalshi and the Commodity Futures Trading Commission. Schilling’s summary of the offence: “the dumb person’s version of insider trading.”

The second case is Bill Simmons, the Ringer founder and podcast host, who lives in California — where FanDuel’s sportsbook is not legal. He had his daughter’s boyfriend log into his FanDuel account from Massachusetts, where it is, passing the two-factor code over to him. Then he described the arrangement on his own podcast, in detail. That potentially violates both FanDuel’s terms and Massachusetts Gaming Commission rules, with penalties ranging from a fine to the loss of gambling privileges in the state.

Schilling’s point about the pair is not that they are sympathetic. It is that both were caught by volunteering the evidence. Santos bet on a publicly observable event that he controlled; Simmons narrated his own violation into a microphone.

The scaffolding underneath

The column walks through how the legal ground was prepared, which is the useful part for anyone who missed it:

  • Daily fantasy sports were classified as a game of skill rather than chance, which is what let DraftKings and FanDuel build a customer base before sportsbook betting was legal anywhere.
  • In 2018 the Supreme Court cleared the way for states to decide sports betting legality individually. It is now legal in some form in 39 states and Washington DC.
  • Prediction markets are not legally gambling at all. Kalshi and Polymarket are regulated as financial exchanges, which is why they can operate nationally while a sportsbook cannot.

The scale is not marginal. Polymarket is valued above $20bn following outside investment, including from Donald Trump Jr. It lists markets on minor celebrity trivia and on live conflicts in the same interface. Schilling notes that the company pulled a market on the likelihood of nuclear strikes once someone inside it recognised the obvious problem — an illustration of how the limits are currently set by operator discretion.

Why the bad-apple model does not scale

The column’s conclusion is that regulation will produce symbolic punishments and cosmetic fixes, and that this is not an accident of enforcement capacity. Proxy betting — someone in a legal state placing bets for an account holder in an illegal one — is trivial for anyone without a podcast network and a taste for self-incrimination. “No rule or regulation or law will make these services clean,” Schilling writes, “because they are inherently built on a messy, morally compromised activity.”

He is careful not to write from outside the practice. He has been in Vegas sports books; he has used FanDuel’s daily fantasy app, still legal in California. The contrast he draws is with his parents’ generation, which treated gambling as a genuinely risky activity rather than a workaround for a state-line inconvenience.

That is the substance of the argument: the enforcement cases that make headlines are the ones where the participants were careless or famous or both, and the ordinary conduct underneath them is not addressed by any of it.