Dear readers,
We hope you all had a better week than former President Donald Trump, who spent the week after his latest federal indictment blaming Joe Biden and “wokeness” for the USWNT’s loss at the women’s World Cup. We, too, are frustrated by the team’s poor showing, but here at Southpaw, we only engage in transparently stupid analysis of a team’s underperformance when there’s a billionaire owner to blame. So instead of dwelling on the Donald’s latest foray into spurious sports punditry, we’ve got an update for you on one of our favorite sports media villains. Happy reading.
-Calder and Ian
After three years of trying and failing to build a successful gambling operation with Barstool Sports — one of the most toxic and overtly reactionary brands in sports media — Penn Entertainment brokered a $2 billion deal this week to throw its lot win with ESPN, leaving behind Dave Portnoy and his merry band of internet weirdos.
For Penn, a casino company that has been unsuccessfully challenging companies like FanDuel and DraftKings for a share of the ballooning sports betting market, the deal was a no-brainer. Portnoy’s proclivity for spewing bad gambling advice — as well the lengthy list of sexual assault allegations that have been made against him — had raised red flags for gambling regulators and dragged down Penn’s stock prices. By swapping Portnoy — a self-described “degenerate gambler” with a history of spewing sexist and racist garbage — for the respected brand of ESPN, the company might actually have a chance of breaking into the sports gambling market. (Just how desperate was Penn to ditch the Barstool brand? In a tax filing, the company announced that it would incur pre-tax non-cash losses between $800 million and $850 million from the deal — so pretty desperate.)
For all the rest of us, though, the deal is a nightmare.
In a video released on Tuesday, Portnoy put some typically self-serving spin on the deal. Instead of getting dropped by his business partner, Portnoy claimed, he had “bought back” the Barstool brand (for $1.00, we might add), triumphantly returning to his rightful place atop his sprawling media empire.
“It’s back to the pirate ship,” Portnoy said, referring to the days when the company had no corporate partners that it needed to please. “For the first time in forever, we don’t have to watch what we say, how we talk, what we do.”
His first two actions as leader of the company? Hiring back a (white) man who was fired by Penn earlier this year for saying the n-word on a livestream, and removing cards from Barstool’s reception desk explain how employees could anonymously report workplace complaints to HR. (“If you want to publicly narc on someone, do it on fucking camera,” Portnoy said in a video bragging about his decision.)
There’s a kernel of truth to Portnoy’s characterization of the deal — after all, he will likely still make a bucketload of cash from the Penn stock options he acquired in the initial deal. But on the whole, this is bad news for Barstool. Without a major corporate partner, Portnoy (who once went by the nickname “Davey Pageviews”) will need to dramatically boost pageviews on his content — and fast. For all of Portnoy’s bluster about how the corporate media is a sham, he’s now operating under the same financial pressures that they are. If Portnoy’s recent behavior is any indication, his plan seems to be to double down on the caustic culture war content that first made him famous.
The irony in this whole situation, though, is that while Portnoy is perhaps the grossest character in this drama, he’s not the only — or even the worst — actor involved in it. That honor would belong to ESPN, a company whose ostensible purpose is to report fairly and impartially on the sporting world, but which has now hitched its wagon to a failing casino company in the hopes of squeezing a few extra bucks out of sports gambling.
This is pretty much the definition of a conflict of interest. ESPN can talk all it wants about erecting guardrails between its gambling content and its news division, but how are real guardrails possible when reporting from ESPN’s news division can move gambling lines, costing or delivering millions of dollars a day to bettors and the company that takes the bets? Ironically, the very fact that Portnoy and his drunken band of bloggers were too busy shouting the n-word on video game live streams to report on any actual sports news meant that any potential conflicts of interest were pretty theoretical. With the ESPN deal, those conflicts are now very real.
To be fair, ESPN has blurred the line between news and entertainment for decades. But it’s worth asking: When you’re assuming the role that Dave Portnoy held directly before you, are you really moving in the right direction?
RODNEY’S ROUNDUP
Do you want to read about . . .
. . . Dwayne Wade’s politics prospect? “Dwyane Wade Was Destined for the Hall of Fame — and Politics?” by Sopan Deb in The New York Times (August 12, 2023).
. . . how sports betting swallowed sport? “Sports Betting Won,” by Amanda Mull in The Atlantic (August 9, 2023).