Massachusetts Officials Hold Hearing Over Concerns Regarding Barstool’s ‘Can’t Lose Parlay’

The Massachusetts Gaming Commission held a hearing on Wednesday over responsible gaming concerns regarding Barstool Sportsbook's now discontinued "Can't Lose Parlay."

The commission deliberated whether the parlay's marketing and language violated state policy.

The “Can’t Lose Parlay” was a popular pre-made wager that Barstool Sportsbook had advertised tongue-in-cheek for the better part of four years before halting the practice in March. A lawyer representing Penn — which owns Barstool — said in the hearing on Wednesday that the company will sign a document that prevents them from resurfacing the promotion.

The promotion had Dan Katz — better known as Big Cat — compile a parlay that users could wager on with the ease of a few button clicks. The parlays were often featured prominently on Barstool Sportsbook's home page and were typically boosted in order to entice users.

Parlays — namely, Same Game Parlays — are sportsbooks’ most profitable wager type. They seldom provide an edge for bettors.

The lawyer representing Penn, Jonathan Albino, said 90% of users lost their first "Can't Lose Parlay" bet. Barstool's argument? That "no reasonable person" would believe that the "Can't Lose Parlay" was as advertised.

Albino said in the hearing that the same legal standard applies to "World's Best Pizza" or "Buffalo wings," which don't contain buffalo. No reasonable person would be tricked into thinking either product is as named, Albino said. He also cited "Crunch Berries," a Cap'n Crunch product that does not contain real berries.

Albino also emphasized the satirical nature of the parlay and Big Cat's "terrible reputation" as a sports gambler.

The hearing was scheduled after a March social media post by Dave Portnoy, which showed his $13,000 wager on a "Can't Lose Parlay" involving four college basketball games. Remarkably, the "Can't Lose" four-leg parlay won despite implied odds of about 28% to do so.

"The majority knows it's satire, but what about the 10% who are young, or who have mental health issues, or have responsible gaming issues," said Brad Hill, a commissioner for the gaming commission.

The commissioners also emphasized the number of new users unfamiliar with the trappings of sports betting who may have been roped in by the "Can't Lose" language — or Portnoy's big win.

"What do we call a reasonable consumer with gambling issues? A majority would know this was a joke. But what is a reasonable consumer in a new industry?" Hill asked.

The gaming commission said it would deliberate and release a final, written decision at a later date.

The news comes on the heels of a contentious approval process in Barstool’s home state of Massachusetts.

While the book was eventually approved, commissioners called into question Barstool founder Dave Portnoy’s commitment to responsible gaming; his “character, reputation and honesty;” and his personal financial history, which includes a 2004 bankruptcy filing reportedly due in part to a $30,000 gambling debt.