Rabbit Hole: ESPN's Gambling Gamble, and Our Perilous Cultural Bet

Media company gets into business with, perhaps, the most deleterious addiction in the world

Rabbit Hole” is a single-topic deep dive column that comes out twice per month for paid subscribers. The free newsletter returns next week.

If CNN suddenly started selling CNN-branded marijuana — let’s call it CNNWeed — you’d probably do a double take. How about Instagram Vodka — maybe they can rename Threads “Shots”? The New York Times keeps scooping up interesting digital properties — what about OnlyFans?

These are not apples to apples comparisons to ESPN’s new deal with Penn Entertainment, formerly Penn National Gaming. But the deal in which Penn effectively pays ESPN $2 billion over the next 10 years to partner them on a sports betting app, called ESPN Bet, among other integrations merging content and gambling, does represent something significant — and ominous.

“Our primary focus is always to serve sports fans and we know they want both betting content and the ability to place bets with less friction from within our products,” said ESPN chairman Jimmy Pitaro in the statement announcing the deal.

Look, says Pitaro, it’s just that ESPN viewers want… frictionless gambling opportunities while watching sports? Maybe, but I’m not convinced.

Instead, the slow creep of gambling in our culture, which has massively accelerated in recent years (legal now in 30 states and getting close in almost every other one) should give any rational person pause. And when a giant media company that produces content, even sports content like ESPN — a company that is a centerpiece of an even larger media conglomerate, Disney, that produces all kinds of other content like news through ABC News and children’s shows — is now going to be a driving force in making betting a focus in its products, it’s time to examine just what this means for our culture.

I want to say at the top — I’m a gambler. I try to make it to Vegas once a year, to play poker, blackjack, and roulette. I’m a regular daily fantasy sports player on DraftKings, where I essentially gamble on a near weekly basis on golf (seriously), among other sports. Back in college at Syracuse, I had a literal bookie that I would bet NFL games through. It is perhaps my own inclinations toward gambling — knowing the challenges of making sure not to extend beyond your limits — that makes me nervous for a future where it’s easier than ever to lose money.

Vice of all places had a great article last year on how “the rise of mobile gambling is leaving people ruined and unable to quit.” For those who have a gambling addiction, it was hard enough staying away from a casino. Now you can gamble your money away from the comfort of your own home.

This ease-of-use is particularly targeted for younger generations. A Pew poll last year found that 19% of U.S. adults said they’ve bet on sports in the previous year. But an NCAA survey this May found that 58% of 18-22-year-olds say they’ve wagered on sports. It’s notable that in the U.K., where sports betting has been legal for far longer than the U.S., they are going the other direction, enacting tougher gambling restrictions, to little outcry from the public.

Again, I’m not a puritan here. I believe that practically anything done in moderation is acceptable. And there are lots of ways to do any number of vices — including gambling — responsibly. But with ESPN spearheading the new shift, we’ve entered a new era of accessibility and media association, with seemingly very little thought put into the implications for our culture.

Because in the grand scheme of our fairly new American social experiment, this wasn’t very long ago:

Catch that on the bottom? That would be “Watch NFL Pro Football weekends on CBS-TV, brought to you by Marlboro.”

So let’s just play this out. Imagine a scenario like this: