By Alex Reimer on

Famous Barstool personalities endorsing sports betting is like Kim Kardashian hawking a pair of SKIMS: it’s part of the brand. The once-renegade company’s rise to the mainstream coincides with the legalization of sports gambling.

Within two years of the Supreme Court paving the way for 38 states to legitimize the practice, Penn Entertainment bought Barstool for more than $500 million. Though the deal didn’t work out for Penn–Dave Portnoy repurchased his brainchild for $1 in 2023–it was a boon for Barstool. The company now enjoys an exclusive deal with DraftKings, pairing the two most influential brands in the country for frat boy 20-somethings.

Barstool is synonymous with sports betting, which is now synonymous with, well, sports.

With that in mind, it wasn’t surprising to see Dan “Big Cat” Katz and two other Stoolies record PSAs decrying a rumored proposal in Pennsylvania to increase taxes on sports betting to fund public transit.

“Politicians got a spending problem, and instead of fixing it, they just keep coming after the fans like you,” said Katz. “Illinois already got smoked with insane tax rates, and now Pennsylvania is on path to do the same thing.”

The provision never appeared in the final budget, and now Barstool is facing questions over whether it illegally lobbied on DraftKings’ behalf.

As mentioned, a Barstool personality shilling for sports gambling is unremarkable. Yet, Katz’s 37-second video drew widespread scorn.

“This the worst company on planet earth that is not involved in the manufacturing of military technologies,” remarked an NBA fan the tune of 22,000 “likes.”

One might notice the outrage didn’t emanate from snotty New York Times opinion writers; but rather, regular-seeming sports fans. Public opinion is moving against unfettered sports betting, and fast.

Another Vibe Shift appears to be afoot, except this one isn’t personified by finance bros feeling liberated to say “pussy” in mixed company. The gluttony and decadence that’s overtaken culture has already led sports fans and sports media to the brink, and the masses want off the cliff.

Scandals and embarrassment 

It’s hard to figure out whether ESPN or the NBA came out looking worse after the FBI announced federal indictments against Chauncey Billups and Terry Rozier. Adam Silver was the first commissioner to endorse legalized sports betting.

A decade later, he cleared Rozier in a league investigation over “unusual betting activity.”

According to the FBI, the NBA missed a lot, including Rozier pulling himself early from a game in March 2023, right when the “unusual activity” was taking place.

Meanwhile, ESPN was unequipped to cover the breaking news. Mike Greenberg, surrounded by a panel of ex-NFL players, bumbled through the segment. Most embarrassingly, when the story first broke, a promo for ESPN Bet was on the screen…

When it comes to soaking in gambling cash, even Disney is overplaying its hand.

One ESPN star who embraces sports betting is Pat McAfee, the perfect mascot for this piggish era. His $30 million annual agreement with FanDuel forever blurred the lines between content and casinos.

Speaking of content, McAfee has total control over his show. That was apparent again when he interviewed Donald Trump on Veterans Day.

“Mr. President, have you ever done an ‘oorah’ to a bunch of Marines?,” McAfee asked, teeing up Trump to denigrate his political opponents, pound his chest and question the Washington Commanders’ name change.

As AA’s Sean Keeley writes, McAfee wants to have it both ways. He claims to be an apolitical actor, except when he’s hosting Donald Trump or allowing Aaron Rodgers to accuse Jimmy Kimmel of cavorting with Jeffrey Epstein.

Stupidly, McAfee said critics of his Trump interview “hate the troops,” as if there’s no other reason anybody would object to having him on.

Once again, McAfee embarrassed the network, and the suits were helpless. ESPN execs rightfully used to fret about alienating the tens of millions of Americans who support Trump.

Apparently, those same concerns don’t apply to the tens of millions of Americans who disapprove of him. Trump’s approval rating is at its lowest point since returning to office.

Shifting political winds

Trump won a majority of young males on his way to a popular vote victory. But the podcast bros who powered the testosterone-fueled fascination are turning against him. Figures such as Joe Rogan, Theo Von and Andrew Schultz have all expressed varying levels of distaste with no holds barred immigration raids.

In a softball interview on CBS, Dave Portnoy was asked why he thinks young men have left the Democratic Party. His answer was a repeat of everything that’s been said for the last year. “My nutshell is, generally they were very anti-normal guys. If that girl is hot, ‘Hey, that girl is hot. I want to drink, I want to party. I like frat parties.’ That was all bad,” he said. “The white guy became the bad guy.”

Portnoy was never challenged in the interview, including when he talked about Barstool’s “good moral compass.” He insists Barstool doesn’t stand for hate or “anything of that ilk.”

That is, unless you’re a “feminist” who complains about Diet Coke cans being too “skinny” or somebody who uses different pronouns.  In Portnoy’s world, those are the powerful figures who deserve a hard time–not him.

“If you are going to pick a fight with me, I will do anything I can to ruin you,” he said.

Much like Bari Weiss, who heads right-wing billionaire David Ellison’s CBS News, Portnoy zeroes in on cancel culture and blue-haired baristas. But those critiques don’t hit as well when cost of living continues to explode, AI is eliminating jobs and feeding societal alienation, and the median homebuyer age is 59. The lives of the disaffected young men who swung right in 2024 aren’t improving.

They are graduating into a bleak job market, and still cannot afford a stable future.

As a result, they’re voting differently. Zohran Mamdani carried young men by 40 points in New York City, while the Democratic governor-elects in Virginia and New Jersey won young men by double digits in their respective races.

Portnoy may still support Trump. But many of the Barstool bros probably don’t.

Gambling backlash

Pro athletes have long sounded the alarm on the harassment they face from angry sports bettors. “We call ourselves zoo animals,” said Red Sox pitcher Lucas Giolito.

But now, they have some company in their panic: sports fans who don’t trust the results. Six in 10 Americans express skepticism about the integrity of sport.

Yet, Americans can’t stop betting. Nearly half of men ages 18 to 49 report having an online sports betting account. Gambling addiction continues to spike, leaving behind a trail of financial destitution and domestic violence.

Since 2018, Americans have spent more than $500 billion on legal sports bets. And what have sports fans received in return? Star players getting criminally charged, a proliferation of ads and bad programming.

A recent Pew Research survey found that 43% of Americans now believe legalized sports betting is bad for society. Leagues and networks are awash in cash, while the fragmented viewing experience keeps getting worse.

Vibes shift back and forth, but standards stay. It’s a shame so many have allowed theirs to fade away.

Talk about a bad bet.

About Alex Reimer

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