DraftKings built an AI tool to find gamblers who were most likely to lose — then used it to target them with "free" bets designed to keep them playing. A New York Times investigation, built on interviews with over 40 former employees and internal company documents, lays out exactly how it worked, and why some of the people who built it now say they regret it.

In this episode, I walk through that investigation in detail, then put it side-by-side with a CBS Sunday Morning report comparing modern sports betting to the crack epidemic of the 1980s — an analogy I was skeptical of at first, having grown up across the street from a crack house in Long Island. By the end, I make the case for why online sports gambling might actually be the more dangerous addiction of the two.

I also bring it back to something I saw myself: at a soccer match in Cartagena, Colombia, I watched a betting company's name replace the league's own — and started asking questions about just how deep that sponsorship goes, and what it might have meant for the outcome of the game I watched.

📌 To read the investigation from the NY Times - 'How DraftKings Uses A.I. to Target The Gamblers Likeliest to Lose' click here 👇🏾 https://www.nytimes.com/2026/09/19/business/draftkings-ai.html?utm_campaign=likeshopme&utm_content=ig-nytimes&utm_medium=instagram&utm_source=dash+hudson

To watch the video from  ⁨@CBSSundayMorning⁩  - 'The addiction of online sports gambling: "Like crack in the 80s"' click here 👇🏾 https://youtu.be/WWaoZRuw8Gw?si=6jnFOYYqvNvO4gd- 

This one deals directly with gambling addiction, so before anything else: if you or someone you know struggles with gambling, help is available right now, free and confidential — call or text 1-800-522-4700, any time, day or night.

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