Dave Portnoy has created a unique media powerhouse in Barstool Sports. Now that the company has become the face of Penn National Gaming’s sportsbook, he and the “Pirate Ship” might have to change their schtick or sink the new endeavor.
While the site has grown exponentially in the past five years and has benefited tremendously from the Penn National investment in early 2020, the envelope-pushing group continues to piss off people. The site has been known for stirring up controversy with league executives, media rivals, and now stock-selling sites.
That’s what makes them so polarizing. However, it could also make them lose opportunities to expand the sportsbook into other states.
Here’s the problem: Barstool Sports isn’t the bread-winner anymore, Barstool Sportsbook is. Now that Portnoy’s company name and logo are emblazoned on this heavily-regulated product, the apathy towards parsing words needs to stop, or at least take a backseat.
Can he? Maybe, but things to change and change fast.
Barstool’s Most Hated Man
Most recently Kevin Clancy aka KFC From Barstool Sports, known for being one of the most hateful people at Barstool while doing anything for clicks, mocked Tiger Woods after he was in a serious car accident.
This wasn’t a single tweet either. No, this was no accident or a simple mistake. After the first tweet, he doubled down even after LA County Sherriff confirmed the crash. He then joked about other so-called hoaxes and even made a very unsympathetic comment about the Jaws to Life being used.
The pronouncement that Tiger Woods’ crash Tuesday was a “hoax” might have been a nadir in their rocky history. And although Clancy eventually issued an apology, it was too little too late when it comes to the people of the internet… 
I deleted my tiger tweets, even though I believe in wearing your bad tweets. But I deleted it because it’s upsetting people, so it’s gone.
I got no problem admitting when I got bad tweets/jokes/moments
— KFC (@KFCBarstool) February 23, 2021
Would the Real “El Pres” Please Stand Up
This is not a bash-Barstool piece. Yes, they upset a lot of people for content deemed offensive. For others (like me) they carry this Northeast-based sensibility of contrarian humor that might remind you of that one friend who’s sometimes writing checks with his mouth his ass has to cash.
Dave “El Pres” Portnoy is really a man for his time. He’s a tireless promoter, having started this site as a sports-betting-focused free newspaper in Boston.
While my colleague Jess Welman has compared him to Russian satirist Anton Chekov, I think he’s more like American media legend Hugh Hefner. At the least, he’s like what wrestling promoter Paul Heyman could have been if he knew how to make money with ECW.
The site grew exponentially in the 2010s. When a bench-cleaning brawl I called in the Federal Hockey League appeared on the site, I had heard of them. Now they have an app, podcasts, YouTube channels, and have become a full-fledged media powerhouse.
The company has benefited tremendously with the investment of Peter Chernin and the addition of CEO Erika Nardini. She serves as not just a major face of the company and the business Yin to the creative Yang that is El Pres.
Raising Millions for Struggling Small Businesses
Yes, Dave Portnoy has made a name for himself by not knowing when to stop yapping, and his non-stop self-hype train is fuel for many of his haters. But you also have to give the guy credit when his big mouth helps save hundreds of small businesses, especially when no one else seems to be doing anything.
Portnoy has raised over $36 Million dollars, supporting over 290 small businesses that were on the brink of collapse due to COVID-19.
And in true Portnoy fashion, this is how it all started:
Politicians Are Stealing the Basic Right To Earn A Living pic.twitter.com/9Yx9Vf1iP1
— Dave Portnoy (@stoolpresidente) December 11, 2020
Portnoy has continued to put his money where his mouth is, capturing the hearts of many people around the country with videos like this:
If this call to Laskara doesn’t make you cry nothing will #barstoolfund pic.twitter.com/tABhtSKwme
— Dave Portnoy (@stoolpresidente) January 2, 2021
Courting Controversy
Barstool is a unique blend of comedy and commentary, ranging from sports and culture to politics and male-targeting clickbait. Sometimes they hit, sometimes they whiff, sometimes they offend and draw ridicule.
There’s a major gap between drawing the attention of Deadspin or a rival site and drawing the attention of state governments where you run a sportsbook or hope to in the future.
After one of his employees quickly defeated former MLB star Jose Canseco in the most recent “Rough n Rowdy” event (their homage to everyman pugilism), Portnoy tweeted that the six-time All-Star took a dive.
That drew a rebuke from a variety of state boards, including the West Virginia state athletic commission, who licensed the event and are investigating the claims.
It’s possible the state will not sanction future contests with the media company.
Dave Portnoy has created a brand so uniquely intertwined with his own person that trying to put a muzzle on him seems about as effective as pushing water back into the ocean. He has been a staunch advocate for free speech and creativity, it almost seems unfair to ask him to stop being so entertaining and edgy.
Sink the Ship or the Book?
Since opening last fall in Pennsylvania, Barstool Sportsbook has competed well in the #3 market in America (by handle last month) and expanded to Michigan. Penn National is rumored to partner up with rival Rush Street Interactive to provide the service in New York.
As the book seeks approval in other states, there will likely come some hearings in which the company will undergo scrutiny from legislators. Some of those may involve Portnoy and others testifying before committees and commissions.
For those reading who didn’t see Portnoy interview Pres. Donald Trump last year, know this: for all his shenanigans, Dave Portnoy is neither a clown nor a fool. He is a smart man, a college graduate, and does not back down.
At some point, Penn National may face a very tough decision. While Barstool has helped the company sign players at a substantially lower acquisition cost than rivals, that strong brand may have to be let go to continue to grow into other states and stay competitive.
Penn National is a gaming company, like FanDuel Sportsbook, DraftKings Sportsbook, and others. While the latter started media arms and signed personalities, PNG wrote a big check and took on a cross between BuzzFeed and Animal House.
If there’s anyone in modern media that invites the target demographic of sports betting, it’s El Pres. He’s a self-made guy from the Boston suburbs who quit the rat race, started his own company, and became a legend without sacrificing virtually anything of what made him unique. If the Chase brothers from Entourage were real actors, Vinny and Johnny would certainly read for the Portnoy biopic (I’d lean towards Drama for the beard and the gruff side). He’s abrasive in an endearing way and cocky to beat the band.
Like a Greek tragedy, his greatest feature may be his downfall. If Portnoy can’t at least alter the brand to a degree, he’ll either have to leave the sports betting business, the reason he started Barstool in the first place, on his own, or be forced out by the corporate suits he often targets.
