The era of Barstool Sportsbook is in Penn Entertainment’s rearview mirror but news has come to light that the company did pay a $25,000 fine to the Massachusetts Gaming Commission (MGC) relating to the defunct sportsbook’s Can’t Lose Parlay.
Penn argued Can’t Lose Parlay was free speech
Barstool personality Dan “Big Cat” Katz regularly offered his picks bundled together as a “Can’t Lose Parlay”, intended to be a tongue in cheek name for a man who, as Penn argued before the MGC that Katz was a notoriously awful bettor.
The group appeared before the commission in June 2023 to argue that the promotion did not run afoul of Massachusetts gaming regulations that prohibit sportsbooks from advertising wagers or promotions as “risk-free”.
Penn Entertainment contended at the time that they did not violate Massachusetts regulations because they believed no reasonable person would assume the parlay was actually incapable of losing. After more than a year of deliberation, the commissions Investigation and Enforcement Bureau (IEB) concluded there was indeed a violation and imposed a $25,000 fine in August of last year.
MA regulators concluded parlay name was misleading
In its memo on the matter, the group noted that, had Penn not terminated the Can’t Lose Parlay in March 2023, the penalty would have been larger.
“The fact that the deception may have dissipated by the time the consumer placed the wager—or even that the consumer placed a different wager altogether—does not change the fact that the deception caused the consumer to wager,” the decision noted.
The decision also noted that the promotion came at the advent of regulated sports betting in the state and it would have been relatively easy for someone new to sports betting and unfamiliar with the Barstool brand and its personalities could have easily mistaken it for some sort of sign-up promotion.
The group also rejected the argument that this was a violation of the group’s First Amendment right to free speech. IEB concluded that, since the MGC was not banning the speech, simply mandating some sort of caveat or disclosure in addition to the speech, there was no violation.
Penn fined $10K for NCAA football wagers
At a MGC meeting on Thursday, the commissioners also approved a recommendation by IEB to levy a $10,000 fine against Penn Entertainment for incidents in November 2023 where the operator accepted 249 bets totaling $12,075 in wagers on college football games where at least one team was not an NCAA Division I team.
There was some debate about Penn’s choice to honor winning wagers and refund losers. As Commissioner Eileen O’Brien noted, these were illegal bets, and patrons should not have been profiting from them. The commissioners ultimately approved the fine by a 4-1 vote, with O’Brien dissenting.
