June 8, 2023 3 min read


Barstool Promotion Faces Scrutiny by Massachusetts Gaming Commission

The Massachusetts Gaming Commission examined whether the marketing tactics and language employed by the promotion violated state policies and regulations

The Massachusetts Gaming Commission recently convened a hearing to address concerns surrounding Barstool Sportsbook‘s highly debated “Can’t Lose Parlay” promotion.

The Rise and End of the ‘Can’t Lose Parlay’ at Barstool Sportsbook

The “Can’t Lose Parlay” was a pre-made wager that gained significant popularity during its four-year tenure at Barstool Sportsbook. However, the company discontinued the promotion in March, and during the hearing, a representative from Penn Entertainment, the parent company of Barstool, assured the commission that they would commit to a permanent ban on resurfacing the promotion.

The promotion was spearheaded by Dan Katz, more commonly known as Big Cat, who curated parlay options that users could effortlessly wager on. These parlays were prominently displayed on the Barstool Sportsbook website and often received boosts to entice users.

Parlays, particularly Same Game Parlays, are highly lucrative for sportsbooks, yet they offer minimal advantages to bettors. According to Jonathan Albino, the legal representative for Penn Entertainment, a staggering 90% of users lost their initial bet placed on the “Can’t Lose Parlay.” Albino argued that it would be unreasonable for anyone to believe the promotion’s claims.

In support of their case, Albino drew parallels to other industries, highlighting the satirical nature of the parlay and Big Cat‘s well-known reputation as an unsuccessful sports gambler. Albino cited examples like “World’s Best Pizza” or “Buffalo wings,” which do not contain actual buffalo meat or berries, to demonstrate that reasonable consumers would understand the promotional language.

Massachusetts Gaming Commission Examines Barstool’s Controversial Promotion

During the hearing, commissioner Brad Hill expressed concerns regarding the potential impact of the promotion on vulnerable individuals, including young people, those with mental health issues, and those susceptible to problem gambling. The commission deliberated on the responsibility to safeguard new users who may not be well-versed in the nuances and risks associated with sports betting.

The Massachusetts Gaming Commission will thoroughly evaluate the matter and subsequently issue a written decision outlining whether Barstool’s “Can’t Lose Parlay” promotion violated state regulations. The decision will shed light on any potential actions that may be taken against the company.

The hearing underscores the ongoing scrutiny faced by Barstool during the approval process in Massachusetts, with commissioners scrutinizing founder Dave Portnoy’s commitment to responsible gaming, as well as his character and financial history, including a past bankruptcy filing attributed in part to a gambling debt.

Ultimately, the commission’s decision will shape the outcome of this controversy and determine the implications for Barstool Sportsbook moving forward. In other news, following Penn Entertainment’s recent acquisition of the remaining stake in Barstool Sports, there surfaced indications that the potential sale of the sports media company is still being considered. Analysts suggested that a sale could bring greater value to Penn Entertainment’s stakeholders, potentially leading to the company’s further growth. However, Penn Entertainment has not officially confirmed any plans for a sale.


Silvia has dabbled in all sorts of writing – from content writing for social media to movie scripts. She has a Bachelor's in Screenwriting and experience in marketing and producing documentary films. With her background as a customer support agent within the gambling industry, she brings valuable insight to the Gambling News writers’ team.

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