Barstool’s ‘Can’t Lose Parlay’ In Massachusetts: Satire vs. Legality

Written By Adam Hensley on June 15, 2023
Is Barstool Big Cat's can't lose parlay satire, from

Is a “Can’t Lose Parlay” truly foolproof if it loses?

Of course not. But in Massachusetts, the phrasing of the promotion has Barstool Sportsbook in hot water.

Barstool has used the phrase to promote special wagers on its sportsbook, and plenty of discussion surrounds the idea of satire vs. legality.

What is Big Cat’s Can’t Lose Parlay?

Barstool entered the Massachusetts sports betting scene back in March, and is one of eight sportsbooks live in the Commonwealth. (That figure includes the beta version of Fanatics Sportsbook.)

In an effort to draw in customers in Massachusetts, the company advertised a “Can’t Lose Parlay” on its sportsbook.

It was essentially a parlay built by Barstool personality Dan “Big Cat” Katz, who then would advertise it, albeit jokingly, as unbreakable. The parlay would typically feature three to four legs.

Katz frequently advertises his parlays on the podcast Pardon My Take. He speaks freely on his failures as a gambler on the podcast, and often times his co-host Eric Sollenberger (better known as PFT Commenter) and others on the show poke holes in his parlay before the games take place.

As a whole, many view the parlay as just another sportsbook promotion on Barstool Sportsbook Massachusetts, not anything that guarantees riches.

Katz is on the record saying how bad of a gambler he is. He is quick to tweet as soon as one of the legs of his CLP fails.

But even so, the Massachusetts Gaming Commission doesn’t want any betting language to imply no risk for potential bettors.

Is satirical language a violation of responsible gambling laws?

Earlier this month, the MGC held a hearing on Barstool’s “Can’t Lose Parlay” advertisement.

Jonathan M. Albano, who defended PENN Entertainment (owner of Barstool Sportsbook), said the parlay is satire. He added that the satire is directed at Big Cat, who advertises the promotion.

“Katz (has admitted) that he is a terrible, terrible gambler, and ‘a loser who never wins at gambling,'” Albano noted.

Katz himself has noted before that no one should listen to his gambling advice, as he doesn’t boast a great track record.

“The (Can’t Lose Parlay) is a humorous, satirical reference to Mr. Katz’s reputation as an awful bettor,” Albano said.

However, state officials want to promote responsible gambling in Massachusetts, and that’s why the topic of this promo is so hot right now.

MGC Investigations Enforcement Bureau attorney Zachary Mercer said the bureau learned of the promotion after PENN VP and Chief Compliance Officer Chris Soriano self-reported the advertisement.

The parlay that flagged Soriano’s attention took place during the college basketball conference tournament schedule and revolved around four of those games. Soon after, the promo was taken down in Massachusetts.

The bureau’s investigation found that Katz’s CLP may violate rules “which prohibits not only unfair or deceptive branding, marketing, advertising, but also those that would reasonably expected to confuse or mislead patrons in order to induce them to engage in sports wagering.”

Not everyone is in on the joke

The “Can’t Lose Parlay” might feel satirical, but it’s walking a gray line.

Any regular Barstool Sports follower or Pardon My Take listener knows that Katz’s brand revolves around humor. And a bettor who’s familiar with how sports betting works knows the risks involved with any promotion, especially parlays.

State officials may understand the Barstool followers would understand Katz’s humor, but they aren’t thinking of just Barstool Sports followers. The state wants to make sure there isn’t any wiggle room when it comes to responsible gambling. Not everyone who gambles on sports in Massachusetts listens to Pardon My Take or knows Katz and his lighthearted demeanor.

Responsible gaming isn’t a joking matter, either. It’s an issue not just in Massachusetts, but across the country. There isn’t room for joking around when it comes to the branding of these promotional advertisements. We’ve seen sportsbook operators change their language, especially those previously dubbed “free bets” or “risk-free bets.”

Barstool will continue to offer its betting in Massachusetts. But its satirical promotions might need to be worded differently, should it want to stay in good graces.

Photo by AP Photo/Paul R. Giunta
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Adam Hensley

Adam Hensley is a journalist from Des Moines, Iowa, with experience covering online sports betting and gambling across Catena Media. His byline has appeared in the Associated Press, Sports Illustrated and sites within the USA Today Network. Hensley graduated from the University of Iowa in 2019 and spent his college career working for the Daily Iowan’s sports department, both as an editor and reporter.

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