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….