Playboy magazine founder Hugh Hefner didn’t just leave behind his wife Crystal Harris, a series of past girlfriends and the famed Playboy Mansion grotto when he died Wednesday at age 91. His death also marked the end of an era for a crowded hutch of corporate lawyers who have represented his company over the years.

From intellectual property concerns to corporate transactions and real estate deals, attorneys from a parade of law firms entered Hefner’s orbit while the Playboy magnate was still alive.