Members of the state gaming commission are raising red flags about the connections between the owners of Plainridge Park Casino in Plainville, which is applying for a sports betting license, and Barstool Sports.

Massachusetts lawmakers approved legislation to legalize sports betting earlier this year, and regulators hope to make such betting a reality at the state's three casinos before the Super Bowl next February. Other options, including mobile sports betting, could come in the weeks and months after.

But at a meeting of the commission on Tuesday, members of the commission questioned representatives of Penn Entertainment, the parent company of Plainridge Park, about its relationship with Barstool Sports to help promote sports betting. Penn bought initial stakes of Barstool in 2020 and recently moved to fully acquire the company for $387 million. The deal is set to be completed early next year.

Through the partnership, Barstool has gotten its own sports-betting app and gotten branding inside Penn casinos. But the company was also the subject of a recent New York Times story highlighting the personal gambling issues of Barstool founder David Portnoy, who has previously reported accusations of sexual misconduct against him. The brand's push to appeal to a younger demographic has become a concern for state regulators.

At a meeting on Tuesday, Commissioner Eileen O'Brien raised questions about the suitability of Barstool to be connected to sports betting in the state.

"You're gonna have a Barstool's-branded sports bar on the premises, according to the proposition that you guys are putting forward," she said. "And I'm concerned about some of the historical marketing associated with Barstool."

Chair Cathy Judd-Stein backed up those questions, saying that regulators are now at a crossroads because of the timing of the Times article, which highlighted the promotion of gambling behavior by people in Barstool's realm that critics say is irresponsible.

"So now we have an obligation to reconcile what is very available publicly as to Barstool and really the significant personality attached to Barstool and what we're gonna do about it as we think about this application," she said.

A man with a radio headset on is mid-speech. He's sitting in front of a neon sign in the logo of a barstool.
David Portnoy, founder of Barstool Sports, speaks during a radio broadcast prior to Super Bowl LIV on Jan. 30, 2020 in Miami Beach, Fla. The San Francisco 49ers will face the Kansas City Chiefs in the 54th playing of the Super Bowl, Sunday, Feb. 2.
Cliff Hawkins/Getty Images Getty Images North America

She pointed out that, besides the issue with Barstool, Penn's presentation on responsible gaming was "excellent."

North Grounsell, the general manager at Plainridge Park, said that Barstool's personalities don't just highlight the benefits of sports betting, pointing to the company's posts about losing money on bets.

Erin Chamberlin, the senior vice president of regional operations for Penn, including Massachusetts and Maine, said that Barstool's employees have teamed up with Penn to talk about the importance of betting responsibly.

"I have seen that it cuts through, I believe, a lot of the clutter, I would say, in terms of these advertising opportunities as well," she said. "It's a very innovative approach to responsible gaming. It speaks to younger people in a different type of voice that I think resonates with them and really makes it stand out a little bit differently."

The commission postponed a vote on granting the sports betting application to Plainridge Park to a later date.