Barstool Sports’ “Can’t Lose Parlay” Bets are Satire, it Tells Massachusetts Regulators

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The Massachusetts Gaming Commission (MGC), held a two-hour adjudicatory hearing on sportsbook Barstool Sports’ “Can’t Lose Parlay” bets promotions this week.

The regulator says the offer violates state rules set out after legalization in January of this year.

Under the Massachusetts legal sports betting framework, operators aren’t allowed to offer promotions that a “reasonable person” might misinterpret.

Confusion around rules like these has led operators in many legal states to stop using terms like “risk-free” in bonus offers. “Can’t lose” may be added to that list if the MGC has its way.

Reasonable Persons

During the hearing on Wednesday, Barstool told regulators it has already ceased the promotion, and has promised not to bring it back. However, its lawyers vigorously asserted the promotion had not, in fact, broken any rules.

The promo in question was heavily featured in an advert during the March Madness basketball tournament season, which is always a popular time for sports betting in the US.

The advert featured sports personality and Barstool podcast host Dan Katz placing a parlay bet on the Barstool app.

It featured the “cant’ lose” strapline several times. Bettors simply had to follow Katz’ picks for increased odds on that particular parlay bet.

In some earlier instances, the promotion came with the promise of a free promotional baseball cap should the wager not come through.

Free hat or not, the MGC claims that the title of the bet means reasonable people may have been misled into thinking that the bet could literally not lose.

Jonathan Albano was the legal representative of Barstool’s owners Penn Entertainment in this case.

At the hearing, he compared the title of the bet to common consumer products with names that don’t actually represent what they are.

“No reasonable member of the public would hold that Captain Crunch Berries are actually made of berries, or that Fruit Loops are actually made of fruit,” Albano said.

“The point I’m trying to convey here, viewed in context, is no reasonable person would view the ‘Can’t Lose Parlay’ as a risk-free or reduced risk wager.”

To back that up, Albano pointed out that 55% of people who used the promotion in March had already taken it up before – even though previous instances of the promotion had seen 90% of bettors lose.

“That I would suggest is compelling evidence that bettors who had hypothetically thought this was a sure thing and lost, surely 90% wouldn’t have come back,” he said.

Terrible, Terrible Gambler

Interestingly, Albano also claimed the advertisement was obviously satirical. He said it heavily leaned into Dan Katz’ online persona as an “awful bettor.”

This wasn’t bought up in the case, but some quick searching reveals Katz did tweet “This can’t lose parlay is most likely going to lose” back in 2019, when the promotion first started in other legal states.

Albano also brought up many instances in which Katz called himself a “loser who doesn’t win at gambling” and a “terrible, terrible gambler.”

However, regulators were not entirely buying that argument.

“I’m worried about the one person who doesn’t understand the irony,” said Commissioner Jordan Maynard.

“Someone who has never heard of Big Cat, who is perhaps on the app for five minutes, sees the words and places the bet. That’s who I’m trying to account for.”

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