Massachusetts Investigating Whether Sports Bettors Really Think a ‘Can’t Lose Parlay’ Can’t Lose

PENN is arguing the promotion did not violate any regulations and that no “reasonable person” would see a four-leg parlay and conclude it was free of risk.

Last Updated: Jun 7, 2023 5:04 PM ET Read Time: 3 min
Barstool Sports 2023
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Would a “reasonable” user of online sports betting sites see somebody on Twitter promoting a “Can’t Lose Parlay” and really think it’s a guaranteed winner? Regulators in Massachusetts are mulling over that very question.

The Massachusetts Gaming Commission (MGC) met Wednesday for a hearing probing the alleged noncompliance of a subsidiary of PENN Entertainment Inc., which owns Barstool Sportsbook

At issue was promotion in March for "Big Cat's Can't Lose Parlay" (CLP) on the app, with the name a reference to Barstool personality Dan Katz, a.k.a. “Big Cat.” Another Barstool personality, founder Dave Portnoy, tweeted that he had wagered $13,458.70 on the four-leg, college basketball parlay.

Commissioners are now weighing whether the promotion broke the state’s marketing regulations. Massachusetts sports betting rules do not allow advertising that implies or promotes wagering as a risk-free proposition. 

PENN is arguing the promotion did not violate any regulations and asking the MGC to rule accordingly. To that end, the casino and sportsbook operator maintains that no “reasonable person” would see a four-leg parlay and conclude it was free of risk. 

“The CLP is a humorous, satirical reference to Mr. Dan Katz’s reputation as an awful bettor,” said Jonathan Albano, a lawyer who appeared on behalf of PENN. “He has said he is a ‘terrible, terrible gambler,’ a ‘loser who doesn't win at gambling,’ and that ‘no one should ever listen to his advice.’” 

Although 15 other jurisdictions have permitted the promotion, PENN has discontinued the CLP in Massachusetts pending the outcome of the regulatory review. Even so, Albano said that as of March 20, there had been 122,428 unique CLP players, 55% of which were repeat bettors, and 90% of which lost their first bet. 

“And that, I would suggest, is compelling evidence that bettors who had hypothetically thought that this was a sure thing and lost, surely, 90% of them would not have come back for a repeat bet,” Albano added. “That, I would suggest, is not surprising given, again, the longshot odds that are disclosed and the need to win multiple bets.” 

With regards to Portnoy’s wager, his social-media following has seen references to his “substantial wealth,” so they would know his bet is one they can’t match, Albano suggested. The lawyer also pointed to the promotion sportsbooks do all the time around massive bets, such as the multimillion-dollar ones placed by “Mattress Mack” and others.

Funny business

The above is just a snippet of what was during the approximately two-hour hearing. The MGC took no action on Wednesday and will instead deliberate in private before returning with a written decision and a potential penalty for PENN. 

Barstool's "Can't Lose Parlay" has come in for scrutiny before. In 2021, the executive director of the National Council on Problem Gambling complained about the promotion to the American Gaming Association, which has a responsible marketing code for sportsbook operators.

In that non-regulatory case, PENN responded the promotion did not violate the code and that on the merits "and in its proper context," the CLP did not guarantee any financial success. The complaint process was closed in March 2021.

Yet comments and questions from the MGC suggest they are taking the matter seriously and will take a long look at CLP. The commission has been meticulous with its work around legal sports betting (which only began in the commonwealth at the end of January), spending long hours reviewing applications and proposed regulations in public settings.

PENN and Barstool, one of several mobile operators in Massachusetts, have been on the receiving end of that meticulousness at times. They are poised for another encounter.  

“I love funny, I love satirical,” MGC Chair Cathy Judd-Stein said at one point during Wednesday’s hearing. “I don't love funny at anyone's expense, however.”

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