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Massachusetts to Investigate Barstool, Dave Portnoy’s Betting License Suitability Amid Responsible Gaming, Character Concerns

Massachusetts to Investigate Barstool, Dave Portnoy’s Betting License Suitability Amid Responsible Gaming, Character Concerns article feature image
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Picture by Getty Images. Pictured: Dave Portnoy.

Penn Entertainment CEO Jay Snowden on Tuesday defended embattled Barstool founder Dave Portnoy and his company in front of the Massachusetts Gaming Commission, which has challenged Barstool Sportsbook’s suitability for a betting license.

The commission received 29 total applicants for a 2023 sports betting launch and has spent significant time questioning Barstool’s merits as a candidate. Barstool Sportsbook operates across 13 states and represents a vital cog in the company’s content machine.

Penn purchased a partial stake in Barstool in 2020 and are set to buy the entire company in Feb. 2023.

“I’m having a hard time reconciling branding a sportsbook in Massachusetts … that I have concerns [for] not only responsible gaming, but simply the character and reputation and honesty of [that brand],” said commissioner Eileen O’Brien.

The concerns were enough to dissuade the commission from granting Penn and Barstool permanent licenses, for now. Barstool was the only retail casino to be granted a non-permanent license in Massachusetts, which means the gaming commission will begin an investigation into the company’s history and practices. If sufficient, the sportsbook can graduate from its temporary license.

WynnBet, BetMGM, MGM Springfield and Encore Boston Harbor have all been fully approved over the last week with no further issues.

A substantial portion of Tuesday’s hearing was centered entirely on Portnoy, whose ethics and character have been called into question amid a history of racism, sexism and insulting behavior.

“I’ll be the first to admit that his personality and style of humor is not for everyone, as would he,” Snowden said in the hearing. “He has said that he has done things in his life that he regrets and wouldn’t do or say today.”

A November article from the New York Times also challenged his fitness as a sports betting spokesperson. Portnoy filed for bankruptcy in 2004 at 26-years-old with $30,000 in gambling losses in one year. In addition, he owed $59,000 to credit card companies and $18,000 to his father, the newspaper reported.

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Snowden said in the hearing that the New York Times story was slanted and “factually inaccurate.”

Despite Portnoy’s personal financial history, he has encouraged followers to bet their “house, kids, family” on games. Gambling is “free money,” according to Portnoy. He has added that it’s “wreckless” not to bet parlays on Barstool Sportsbook “every single week.”

“While stories about his personal life may fuel clicks and sell subscriptions similar to the New York Times article,” Snowden said. “Mr. Portnoy has not been part of any law enforcement investigations we are aware of and he has not been party to any criminal or civil litigation or financial settlements based on any of these allegations against him.”

Barstool’s attempts to lure in underaged bettors were also examined. Penn and Barstool were fined $250,000 in Ohio after targeting University of Toledo students to sign up for their sportsbook.

Snowden said the advertising campaign was a mistake and a result of a lack of oversight.

Barstool made an agreement with Massachusetts gaming officials on Tuesday to disallow anyone younger than 21 from attending Barstool’s live college football shows.

Portnoy’s substantial unit sizing — in which he gambles up to $500,000 on a single spread, moneyline or prop — was also illuminated by the commissioners amid responsible gambling concerns. He has boasted in the past about typically wagering $25,000 per bet.

Snowden said Portnoy’s net worth allows him to wager the amount he does.

An interesting quirk to these wagers is that Portnoy and other Barstool employees are permitted to bet big money on their own book, a conflict of interest avoided at other companies, which prevent workers of any kind to wager on the same platform.

Snowden said Portnoy, Dan Katz — better known as “Big Cat” — and other Barstool talent are not direct employees of Penn. Rather, some workers are permitted to wager with Barstool Sportsbook — despite directly benefitting from it — because they created separate loan-out companies that keep them distinct from Penn Gaming.

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