Hugh Hefner
Photo: Joe Seer/Shutterstock.com

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.

“Playboy has a huge trademark portfolio,” Ballard said. “Since I've taken it over I've seen reports that it's one of the top 10 most recognizable brands in the world, along with [the likes of] Coca-Cola. It's an honor to represent such a famous brand and it's been an incredible experience for me and for Venable.”

Ballard also noted that Hefner had a strategy to take the Playboy brand international long ago, “before many western companies were.” That included going to China more than two decades ago, where even though censorship kept the magazine off the shelves in the country, the company carved out a market by licensing its bunny logo for use on clothes and apparel, among other products.

Outside the United States, Ballard said, the brand is often associated more with the luxury lifestyle Hefner embodied and the notion of the “good life” than it is with nude models.

“China didn't even have the magazine,” Ballard said. “But what they do like is bunnies and rabbits.”

Of course, Hefner needed more than trademark help over the years. In one case the company tapped Dick DeGuerin, a trial lawyer most known for high-profile criminal defense work such as the murder case against real estate scion Robert Durst. Playboy reportedly used DeGuerin to help it navigate a dispute over a roadside art installation near Marfa, Texas.

Here's a look back at a few other notable representations:

• Hefner was long known for his free speech advocacy, and his foundation has given out a First Amendment award since 1979. So it's not surprising that his company was embroiled in the high-profile free speech battle, United States v. Playboy Entertainment Group, a 2000 U.S. Supreme Court case that struck down restrictions that Congress had placed on cable operators running “sexually-oriented” television programming during certain daytime hours. That case put several lawyers to work­, including Robert Corn-Revere, now of Davis Wright Tremaine, who handled the 1999 high court argument for Playboy. At the time, Corn-Revere was a partner at Hogan Lovells predecessor Hogan & Hartson.

• Several large firms played roles in a 2011 corporate transaction that took Playboy Enterprises Inc. private. Skadden, Arps, Slate, Meagher & Flom mergers and acquisitions partner Rodd Schreiber represented Playboy Enterprises in the deal, while Hefner called on a Munger, Tolles & Olson team that included Robert Knauss, who now serves as general counsel for the private equity fund Warburg Pincus. Kaye Scholer, which was then yet to merge with Arnold & Porter, advised Playboy's board of directors on the deal.

• Sheppard Mullin Richter & Hampton's Jennifer Redmond represented Playboy in a whistleblower lawsuit brought by a former accounting executive who alleged she was wrongly fired after reporting potential fraud in the company's finances. A federal jury handed down a $6 million verdict against Playboy in 2014, although the case was later voluntarily dismissed in light of a settlement, according to court records. Playboy later sued Sheppard Mullin for malpractice in connection with the verdict, and that case was voluntarily dismissed from California state court earlier this year.

• A pair of Los Angeles-based law firms handled a record-setting 2016 real estate transaction in which Daren Metropoulos, a billionaire tied to family investment firm Metropoulos & Co., paid $100 million to buy the famed Playboy Mansion from Hefner's company. Metropoulos tapped a team from Cox, Castle & Nicholson, led by partners Paul Titcher and Ira Waldman, to advise on the sale, while Eisner Jaffe partner Loretta Thompson served as outside counsel for Playboy. In addition to the eyebrow-raising value of the deal, it had an unusual provision: Hefner was allowed to live out his remaining days there. With Hefner's death, Metropoulos is reportedly ready to start renovating the mansion.