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Welcome to Over/Under, a newsletter on prediction markets, gambling, and the culture of risk in America. Platforms such as Kalshi and Polymarket are changing how people interact with modern life—politics, video games, movies, and even the weather. Sports gambling is booming. If you have a hunch, and an internet connection, you can bet on almost anything.
Even for those who don’t partake, this phenomenon is difficult to ignore. Athletes are signing multimillion-dollar sponsorship deals to expand their reach. Livestreamers spend hours playing slots and other online casino games while millions watch. News organizations (not ours!) are entering into corporate partnerships with top prediction markets. Last month, a titanic image of Sydney Sweeney appeared on a billboard in Times Square, coaxing viewers to log on and trade. And the betting itself is just a few taps away on our smartphones.
In some ways, this all feels reminiscent of the crypto boom I covered in the early 2020s, when a once-niche industry was repackaging itself for the mainstream, and opportunistic ecosystems were sprouting up all around it. Today, users are betting on things that would make at least some of the bookies of the past squirm: war, disease, and natural disasters. Politicians are betting on their own odds of being elected. A master sergeant in the Army allegedly deployed insider knowledge on Polymarket to profit from the kidnapping of Venezuelan President Nicolás Maduro. Federal prosecutors are just starting to crack down on the insider-trading problem—and the industry is still figuring out how it wants to respond.
You probably have questions. I know I have questions. In this newsletter, I hope to explore not just how betting works today, but also how the risks we take shape the society we live in.