Matt Levine, Columnist

Barstool Sold High and Bought Low

Also WeWork’s decline, Yellow’s equity value, Target as a securities-fraud target and a Reata M&A typo.

One way to think about it is that if you are a gambling company, and it is 2020 and sports gambling is becoming broadly legal in the US, you will want to market sports gambling broadly to potential customers, and the best way to do that might be to team up with a popular sports media brand. Name your sports gambling site after the sports media brand, and at the top of every article on the media brand’s website have a little call to action like “I see you are reading about the Mets, would you like to place a wager on the Mets?” You are fundamentally a gambling company, which is still a bit suspicious and seedy to some sports fans; you will get more customers and trust and goodwill from a sports company.

So, when sports gambling is becoming broadly legal in the US, you strike a marketing partnership with the very biggest and best sports media brand you can get. Which will not be that big or that good. You’re not going to get ESPN. It’s early days for broadly accepted sports gambling, it’s still a little edgy, and the best you will do is teaming up with kind of an edgy sports media brand. Barstool Sports, for instance, the bro-y and controversial site that appeals particularly to young men. And you will pay it a large amount of money for a licensing deal where you get to name your sports gambling site Barstool Sportsbook and advertise it on Barstool’s media properties.