In California, Friday reportedly saw millionaire publisher and businessman Larry Flynt lose his legal challenge against a state law that forbids licensed casino owners from being involved in the operation of similar out-of-state venues.

According to a report from the Courthouse News Service, Flynt had joined with the card room-operating father and son pair of Haig Kelegian Sr and Jr to argue that California’s Gambling Registration Act was obsolete and had prevented him from investing in profitable casino ventures for some of his out-of-state adult businesses in 2014 and 2015.

Reportedly at issue was the $210,000 fine levied on Kelegian Jr by the California Bureau of Gambling Control after the businessman transferred ownership of a Seattle card room to his wife in 2010. In the complaint, the plaintiffs purportedly alleged that the one-time penalty had resulted in a lasting impact and barred Flynt from becoming involved with lucrative casino enterprises in Colorado, Mississippi and Nevada.

Flynt, who today is celebrating his 75th birthday, is the president of Larry Flynt Publications, most notably known for Hustler magazine, and also owns the Hustler Casino in the Los Angeles suburb of Gardena as well as the nearby Larry Flynt’s Lucky Lady Casino.

The Courthouse News Service reported that Flynt had additionally unsuccessfully argued that the 1984 law had outlived its rationale, which is to keep organized crime out of California’s casinos, after using the updated regulations in neighboring Nevada as an example.

However, Judge John Mendez from the United States District Court for the Eastern District of California reportedly ruled against the trio with prejudice because the filing of the lawsuit had fallen outside of a two-year statute of limitations. He moreover purportedly found against the plaintiffs after determining that they had failed to allege continuing harm.

“The court also finds that any further amendment would be futile and, therefore, grants defendants’ motion to dismiss with prejudice,” read the ruling from Judge Mendez.

The Courthouse News Service reported that in 2002, a survey funded by the state had recommended allowing publicly-traded companies to operate card rooms; before citing attorney Paul Cambria as revealing that Flynt now intends to appeal the decision.