Understood: The Big Bet

When single-event prop betting was legalized, athletes suddenly became more than players, they became betting chips. Their points, their rebounds, and their injuries now win or lose people money. Sometimes, a LOT of money. And if everybody's gambling on athletes, what happens when an athlete like Jontay Porter starts betting on — or against — himself?

Featuring:
Danny Funt, Anthony Milton, Dr. Jim Borchers, DeMaurice Smith

What makes sports betting so addictive? We explore how sportsbooks take lessons from casinos to keep users hooked. When gambling is legalized everyone is going all in including Toronto Raptor Jontay Porter, and two everyday bettors: a former college athlete who spiraled into addiction, and a sharp bettor who actually beat the system — only to be blacklisted by the apps and forced into a shadow network.

Featuring:

Danny Funt, Anthony Milton, Travis Mistratta, Nigel Eccles, Dr. Nigel Turner, Nik Bonaddio

How did sports betting go from being illegal to being EVERYWHERE? The answer lies in the convergence of daily fantasy sports apps, a bombshell New York Times op-ed, and the potential of a multi-billion dollar payout. And we tell the story of how a pivotal Supreme Court ruling set the stage for one of the biggest scandals in sports history — one involving a Toronto Raptors bench player named Jontay Porter.

Featuring:
Danny Funt, Anthony Milton, Nik Bonaddio, Nigel Eccles, Stephen Master

Once associated with bookies, organized crime, and backroom bets, sports betting is now one of the fastest-growing industries in North America. This is the story of how it went mainstream — and who’s paying the price. Four episodes, releasing weekly starting Monday, October 5, 2026.

When you talk to a chatbot, it can feel like technological magic. But behind the illusion of engineering brilliance is an open secret in the tech industry: that tens of thousands of workers, many based in Africa, spend their days teaching AI how to speak, respond, and even simulate intimacy. Michael Geoffrey Asia is one of them. He’s part of the hidden human workforce behind the bots.

We look at the emotional toll for the humans on the other side of the screen, and ask if users are pouring their secrets and souls into the systems, believing them to be private, unfeeling machines — how private is your AI relationship?

This episode features Karen Hao, Michael Geoffrey Asia, and Shuby Goel.