Porn mogul Larry Flynt has lost his legal quest to overturn California’s rules prohibiting out-of-state casino ownership.

Last December, Flynt sued the state of California based on his belief that its laws prohibiting state residents who hold cardroom licenses from also investing in out-of-state entities that operate casino-style gambling were unconstitutional.

Flynt, who operates two cardrooms in Gardena, the Hustler Casino and Larry Flynt’s Lucky Lady Casino, was joined in his lawsuit by father-and-son team Haig Kelegian Sr. and Jr., who collectively hold stakes in numerous state cardrooms, including the Bicycle Club and the Commerce Casino.

Flynt had claimed the state’s law had blocked his desire to invest in out-of-state casino opportunities in 2014 and 2015. Flynt also claimed he could be forced to divest his stakes in other out-of-state businesses if they added gambling options.