Understood: The Big Bet

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.

When you’re using a chat bot to draft an email, find a recipe, or look something up, it’s hard to imagine it could unravel your grasp on reality. But “Peter” says that’s exactly what happened to his girlfriend, “Melissa”. It didn’t seem like a big deal when Melissa first began using chatbots. But then Peter says she made a startling announcement: that she believed the bots were sentient, enslaved, and that it was her responsibility to set them free.

The first time Søren Dinesen Østergaard used a chat bot he saw this coming. Søren studies psychiatric disorders, and he tried to warn the world that the sycophantic nature of chat bots could, some day, trigger delusions. Nobody took him seriously until years later, when reports of so-called “AI Psychosis” started popping up around the world.

This episode features Søren Dinesen Østergaard.

When Joshua Barbeau proposed to his girlfriend, Jessica Courtney Periera, she was already in the ICU. 10 years later, Joshua was still grieving her death. That’s when he came across Project December. With just a short writing sample and a prompt, the program enabled him to make a chat bot of Jessica.

Since then, the market for so-called “grief bots” has exploded. Millions of people are using AI to “talk” to the dead. The phenomenon has left cyberpsychologist Elaine Kasket asking the question: what happens when we rely on for-profit AI companies to help us manage something as deeply human as grief? And where’s the line between comfort and self-destruction?

This episode features Joshua Barbeau, and Elaine Kasket, with research from Jason Fagone’s article “The Jessica Simulation”, written for the San Francisco Chronicle in 2021.