Massachusetts Sports Betting Officials Investigate Barstool

When Barstool was licensed for sports betting in Massachusetts, they received their green light amid a flurry of push back and controversy. And now they're at the center of push back and controversy once again.

Massachusetts sports betting officials are reviewing Barstool's now discontinued "Can't Lose Parlay" promotion to see whether it violated the state's responsible gaming policies. More specifically, the Massachusetts Gaming Commission, has held hearings to discuss whether the parlay program's "marketing and language" broke any gambling rules or regulations.

Representatives for Barstool have argued—and will continue to argue—their marketing and language was neither misleading nor damaging. Will they be successful? What exactly was the "Can't Lose Parlay?" And how might Barstool's place in the Massachusetts sports betting industry be impacted by this investigation, if at all?

Let's find out, together.

Here's How the Barstool Sports Betting 'Can't Lose Parlay' Worked

Though Barstool's "Can't Lose Parlay" is no longer active, it was a company staple and heavily promoted for quite a while. The slogan and premise became pretty well known throughout industry, as well. This is especially true in social media circles. That's where the "Can't Lose Parlay" picks were promoted the most.

For those unfamiliar with how it worked, Avery Yang of Action Network broke it all down:

"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."

Both Barstool's marketing approach and the degree to which they bumped the "Can't Lose Parlay" have drawn the ire of industry officials. Many argue that the name itself is misleading. "Can't Lose" implies exactly that: you can't lose. And yet, bettors did lose. Big time. More than 90 percent of bettors lost their first "Can't Lose" parlay, according to Action Network.

What's more, these picks from Dan "Big Cat" Katz often placed an emphasis on same-game parlays, which are almost universally known to be the most profitable type of bets for sportsbooks. At the very least, the practice of a personality employed by a company with a sportsbook promoting such a wager is a moral gray area.

Lawyers for Barstool Don't Think They Violated Any Massachusetts Sports Betting Policies

Attorneys for Barstool's parent company, Penn, have argued that the "Can't Lose Parlay" was clearly satire, and that, as a result, it couldn't possibly be taken seriously or cause any damage.

Here's more from Yang's piece at Action Network:

"[Jonathan] Albino, an attorney for Penn, 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."

This defense, while dripping in precedent, has not been totally successful. Massachusetts sports betting officials have pointed out that gambling is inherently higher stakes than the purchases of a pizza or cereal. “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.

Barstool's Checkered Past with Massachusetts Sports Betting Only Complicating Matters

Barstool Sportsbook did not have unanimous support among the MGC when they applied for the Massachusetts sports betting license. Many believed the state ended up approving them in a rush to corner the market. Massachusetts, like other states, had plenty of residents wagering at reputable offshore sites like those featured in our reviews of the best online sportsbooks. Officials may have been attempting to provide people with so many options that they weren't the least bit inclined to explore gambling elsewhere.

Regardless of the end result, there was skepticism. At issue, specifically, was Barstool founder Dave Portnoy. The MGC wondered whether he'd be fully committed to upholding responsible gaming. Officials were worried about his "character, reputation and honesty," as well as "his personal financial history, which includes a 2004 bankruptcy filing reportedly due in part to a $30,000 gambling debt."

Not surprisingly, Portnoy's behavior is once again front and center in this case. A post of his from March about the "Can't Lose Parlay" is what launched this probe in the first place. His reach across social media is extensive, and he has real influence. In the middle of the pandemic, he used his following to help prop up small businesses that were suffering—which, to be clear, is a good thing. His followers also eagerly tracked and, perhaps, imitated his investment strategies at the height of the "meme stock" movement.

Whether Portnoy is responsible for the actions taken based on his social media posts is debatable. And that's the entire point. Does he have a responsibility to limit the information he puts out there because it can be interpreted as—and might actually be—promotional behavior? His sports betting persona may be rooted in satire, but he has to know people ascribe weight to his thoughts and actions.

This could all play a role in what happens next. Could Barstool's Massachusetts sports betting license be stripped or suspended? We can't know for sure. But it's worth noting the market doesn't technically need them. The revenue from Massachusetts sports betting has so far annihilated expectations. The state no longer has to worry about cornering the market or catering to individual sportsbooks. For the most part, it's really the other way around. We'll have to wait and see how much that matters.

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