The Sons Also Rise
In 1979, Willie Mays got a gig as a “‘goodwill ambassador’ for the Bally’s Park Place hotel and casino in Atlantic City. It was not a full-time job. Mays’ job was basically to show up and be famous while doing meet-and-greets at corporate and charity events.” Back then, even that relatively minor connection with gambling was enough to get Mays banned from baseball. A few years later, Mickey Mantle suffered the same punishment for a similar transgression. Times—and values—have changed. Today, Major League Baseball has a casino as one official gaming partner and a betting app as another, and gambling has basically merged with professional sports. Just ask the players. The Athletic (Gift Article): MLB players reveal a modern toll of legal gambling: Threats, DMs and encounters.
+ If betting apps weren’t enough, now prediction markets are getting in on the action. Everyone knows that participating in prediction markets like Kalshi, especially when it comes to sports, is the same thing as betting. That’s why sports fans see prediction market ads everywhere, and why Kalshi is partnering with many teams, including my San Francisco Giants. The marketing push mirrors those of gambling companies because prediction markets are gambling companies. As Nick Brown, the Democratic attorney general of Washington, explains, “You can go onto a site and place money on the outcome of some sports activity. That’s the same thing as gambling.” One would assume that the notion that gambling is the same as gambling would be a self-evident and accepted truth. But this is 2026, and times—and values—have changed; so don’t bet on it. Here’s one thing you can bet on: When there’s something this obviously shady happening, the first family probably isn’t far from the action. “Last month, 44 states signed a letter attacking the platforms as a ‘new form of casino’ preying on young people.” But the federal government is doing everything it can to stop states from regulating the industry. Why? Just follow the money, Sonny: “In January last year, Kalshi hired Donald Trump Jr. as an adviser; his compensation included more than $300,000 in Kalshi shares, which have multiplied in value. Last year, the president’s son also joined Polymarket’s advisory board and bought a stake in the company via 1789 Capital, his investment firm.” NYT (Gift Article): Clash Between Prediction Markets and States Sets Off a Furious Political Battle.
+ The Trumps famously failed in the casino business. But they’ve found a business they seem really good at: government corruption for personal gain. WSJ (Gift Article): Drone-Defense Startup Needed Connections, so It Hired Eric Trump. “The agreement comes as the president’s two eldest sons have been amassing stakes in numerous small U.S. government contractors through investments or advisory work, positioning the brothers to benefit from spending and policy decisions by their father’s administration … It marks a notable pivot for the brothers, who for years were focused on their father’s turf of real estate, golf and branding. But since the start of their father’s second term, they have become highly active investors and advisers, also taking stakes in companies involved in tungsten mining and nuclear energy—while growing their crypto holdings.” (Say Hey Kid, meet the Pay Day Kids.) “”What’s remarkable about it is that it’s put in writing,’ said Jessica Tillipman, associate dean of government procurement law studies at George Washington University. An agreement like Eric Trump’s would be expected to trigger ‘the giant circle and red flag from the compliance department’ at a traditional U.S. corporation, she said.'” As a wise man once (or maybe twice) said: Times—and values—have changed.
