Gambling, Games & Greed

Confession: I’m not much of a gambler. Well I suppose it all depends on who you’re comparing me to… Let’s take a look at my stats.

All time, looks I’m -$100.47 in the hole. Not terrible. Some of you might see this and think I am a gambler, perhaps? It’s all relative. In my social circles, this is nothing.

Generally speaking here’s why I don’t really gamble: 1) I hate losing money and 2) I’m a bad gambler. I gamble with my heart and fandom, which, you’ll soon learn, is the absolute WRONG way to bet.

That said, I get the appeal. Betting on a game does make it more fun, especially when it’s on your team to win. Suddenly, a random Wednesday night NBA game becomes the most important event of your week. But after listening to Michael Lewis’ Against the Rules podcast, I’m looking at the whole industry a little differently.

A Brief History & Some Context

Here’s the quick history: Sports gambling used to be illegal almost everywhere in the U.S. But, it was still happening everywhere. The argument for legalization was, “Hey, it’s already happening. If we legalize it, we can help identify those with serious problems & get them help.” So, in 2018, the Supreme Court approved & legalized it, and now it’s everywhere.

Companies like DraftKings and FanDuel are printing money. In 2022, Americans bet $93 billion on sports. It’s so mainstream that you can’t watch a game without seeing ads for odds boosts, bonus bets, and parlays. Gambling isn’t just part of sports anymore—it’s inseparable from them.

Michael Lewis—The author behind Moneyball, The Big Short, and The Blind Side—is one of the smartest voices out there. And in his podcast, Against the Rules, he dives into the ethics of sports gambling, and he doesn’t pull punches.

Unlike most media platforms, Lewis refuses to take sponsorship money from gambling companies. Instead, he exposes how they exploit their most vulnerable customers while pretending to care about “responsible gambling.”

He calls it “human fracking,” where the gambling industry is just fully exploiting our fandom. Sports betting companies don’t care if you gamble responsibly. In fact, they’d prefer you didn’t.

Here’s how they play the game:

• They push parlays EVERYWHERE. Why? Because parlays have terrible odds for you but amazing profits for them. A good gambler (& yes, they do exist) would never touch a parlay with a 10 foot pole.

• I mean, look at the front page of my DraftKings app right now…

  

• They slap “If you have a gambling problem, please call 1-800-GAMBLER” on every ad to cover their asses.

• Then, they roll out the red carpet for their biggest losers. VIP perks, concert tickets, special odds—the more you lose, the more they reward you.

Lewis actually pressure tested all of this with his podcast producer, LJ. She is not a gambler (nor a sports fan), however, he had her make accounts & start placing bets. On FanDuel, she placed bad bets. Parlays galore. She quickly lost about $10,000, & within a few weeks received a text from a ‘VIP Host’ from FanDuel inviting her to a concert in a box at MSG as well as free bonus $$ to place more bets. On the other app, at DraftKings, she placed “smart bets” using advice from a professional gambler. Straight bets & money-lines. She made money quickly, about $8k. After a couple weeks, her account was restricted because she was winning. DraftKings flagged it for “Suspicious activity” & it was impossible to get in touch with anyone to explain why.

The house doesn’t just win in sports gambling right now; the house rigs the game. What if there was a stock market where the smartest stock traders where just not aloud to participate? Doesn’t really sound like a “free market” to me.

The math is simple: Straight bets: You win ~50% of the time if you’re a decent gambler & know what you’re doing. Parlays: You win almost never.

I’m not here to tell you how to live your life. If you want to throw down $20 on a game to make it more fun, go for it. Just know the system isn’t built for you to win—and the odds get worse the more you play.

Your homework this week is to listen to the podcast here → Michael Lewis’ Against The Rules. It’s worth it & you’ll probably never place a bet ever again.

See u next week.