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.

Venable partner Marcella Ballard, who has handled global trademark enforcement for Playboy and some of Hefner's marks since 2011, said she didn't have much personal contact with the adult magazine pioneer—although she did meet him briefly at an event, she picked up the representation after Hefner had taken a step back from the company's day-to-day operations. Still, Ballard said it was easy to appreciate Hefner's business acumen and his early vision to expand the Playboy brand—along with its trademark bunny head icon—beyond the original magazine.