'Can't Lose Parlay' Hearing in Massachusetts: Barstool Sports Fate to be Decided Soon

Written by:
Gilbert Horowitz
Published on:

One of the biggest controversies within the US regulated sports betting market centers around the push to get customers betting parlays.  A parlay bet requires that each leg of that bet win in order to receive much higher payout odds.  But ask yourself this: When was the last time all three of your picks in a given day actually won?  Even the best handicappers will find it close to impossible to go 2-1 daily on a consistent basis.  In other words, over the long haul, it turns out to be more profitable simply betting the outcomes on a single game.


Parlays are deemed to be legal bets in all US states.  Barstool Sports, however, took things a bit further by advertising some of its parlays as "risk free".  That was the basis for Wednesday's hearing in Massachusetts.

The “Can't Lose Parlay” was a popular, since pulled, pre-made wager that Barstool Sportsbook had advertised tongue-in-cheek for the better part of four years.  It only became an issue after Penn National acquired the company and sought a sports betting license out of Massachusetts. 

For the promotion, Dan Katz — better known as "Big Cat" — grouped a series of bets together.  Few actually won as a group.

The Barstoolsports "Big Cat Can't Miss Parlay" was on the radar of regulators months before Barstool Sportsbook launched in Massachusetts.  On Wednesday, TheMassachussetts Gaming Commission was holding an adjudicatory hearing on its legality.  Fines could be levied as a result of any determine improprieties.  The Commission stated from the onset they would not be making a determination on Wednesday.

Bill Speros, Senior Betting Analyst at Bookies and the GDC Group, as well as a columnist for the Boston Herald, was present at Wednesday's hearing.  He broke it all down via his Twitter page.

Jonathan M. Albano, a First Amendment lawyer at Boston's Bingham McCutchen representing Barstool Sports parent company Penn Sports Interactive (PSI), noted that, once PSI became aware of the MGC's concerns about "Can't Lose Parlay", Barstoolsports stopped the parlay and will put it in writing that they will not resume When CLP first offered in MA, it had been offered in 15 jurisdictions with no complaints.

Speros also noted that Commissioner Eileen O'Brien was only member to question Penn National attorneys in regard to a tweet by Barstool Sports founder Dave Portnoy posting about a $13K+ bet on "Can't Lose Parlay" and how that did not run afoul of regulations not endorsing a particular bet.

Albano stated: "We ask that "Can't Lose Parlay" and Mr. Portnoy's Tweet did not constitute a violation of state statues. No reasonable person could assume they were engaging in a risk-free bet. No "CLP" offerings have been made since and will permanently terminate offer."

Albano added that 55% of "Cant' Lose Parlay" players were repeat players and 90% lost their first bet.

"Surely they would not have come back"

The hearing adjourned shortly before 2:30 pm Wednesday.

- Gilbert Horowitz, Gambling911.com

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