Djamilla Rosa Cochran/WireImageHugh Hefner adored women.
Though posthumously he's been both celebrated and slammed for bringing Playboy and everything it signified into this world, and his ultimate contribution to the sexual revolution is likely to forever remain a subject of debate, there's no doubt that he surrounded himself with women because he couldn't get enough of them.
But while the faces around him changed over the years, one thing was a constant for Hef, and that was his devotion to the empire he had built—the biggest love of his life.
Rumors flew for years about the true state of Hefner's health as he entered his 80s and still maintained the lifestyle of, not just a much younger man, but a boy who had been told he could have all the candy in the world at his disposal.
It wasn't until last year, however, that reports placed him in more dire straits—even prompting the man himself to tweet last October, "I wish the tabloids had informed me a little earlier in the week that I'm sick. I would have cancelled my weekend plans."
But as he rounded 90, it was impossible for those close to him not to see that age was finally catching up with the indomitable Hugh Hefner.
"He's not as involved in his company anymore and has handed over much of his power to people on the board," a close Hefner family friend said in the spring of last year. "He just doesn't seem to be as interested as he used to be, and while he still likes to be aware of everything, his age has meant that certain people have started to take advantage of him.
"He seems to not be as sharp as he used to be. It's not that he's suffering from dementia. It's just that he has other things on his mind and he's more easily swayed by outside forces."
Hefner put together the first issue of Playboy at the kitchen table in his Chicago apartment in 1953, having scraped together $8,000 ($1,000 of which came from his mother) and paid $500 for one nude and one clothed photo of Marilyn Monroe, taken during a 1949 calendar shoot that she earned $50 for before her career took off.
Playboy's debut sold 54,000. In the 1970s, circulation rose as high as 7 million—and that's where it peaked, as other, more graphic magazines like Penthouse and Hustler jockeyed for newsstand (and under-the-mattress) space.
But despite inevitable decline in subscribers, the Playboy brand had become larger than life.
It also, ironically, became a family business.
Daughter Christie Hefner, the publisher's eldest child from his first marriage, joined the company in 1975 and served as CEO and chairwoman of Playboy Enterprises for two decades. When she stepped down in 2009, she had become the longest-serving female CEO of a public company in U.S. history.
"I've always known that I wanted to move on at some point in my career," Christie Hefner told the New York Times upon announcing her intent to leave in December 2008. "I've given a great deal of my life to the company."
Scott Flanders, who assumed the role of CEO in June 2009, told The Hollywood Reporter in September 2011 that Playboy Enterprises had effectively become a licensing company, its famous name and bunny head logo still in demand. According to Flanders, the company was approaching $50 million in revenue for the year, a $20 million increase from when he first started.
Hefner remained the controlling shareholder, as well as editor-in-chief of the magazine. "I'm still very active in certain aspects," he told THR. "I pick all the covers, pick all the Playmates, pick all the pictorials, edit the letters, party jokes, cartoons, approve all the layouts."
At the end of the day, Hef said, "the business end of business has never interested me." Regretting to THR that the company had gone public in 1971 ("to be a nice guy to my executives," he said), Hefner had arranged for it to go private again in 2011, securing a $207 million purchase price with Rizvi Traverse Management that left him with a roughly 30 percent stake and RTM with the rest.
The most controversial creative shift at Playboy in decades occurred in the fall of 2015, when it was announced that the magazine, starting in March 2016, was no longer going to include full frontal nudity. Curve of a backside, yes. Bare breasts, no.
Flanders said that Hefner was in agreement with the sea change, an admission that Playboy couldn't really compete with free porn on the Internet and an attempt to recapture the magazine's culturally relevant heyday by doubling down on the journalistic and upscale-male-lifestyle content while still featuring sexy photos of women. Playboy.com had already dispensed with naked women in August 2014—though your office security will still caution that you're about to enter a porn site if you need to look up interview quotes.
But around the time the print change took effect, much to the dismay of fans of the way things were, it was hard to say how Hefner really felt about it. More and more those days, "Hef would just go with it" when an idea was proposed to him. "He would give in easier to things," the family insider said, "whereas previously he might have given certain decisions more thought and relied on his own instinct a little more."
Son Cooper Hefner, meanwhile, was outraged enough for the both of them.
An opponent of the decision to get rid of the nudity from the start, the now 26-year-old—whom his father had championed as the new public face of the company—said last year that he was taking a "massive step back" from Playboy.
"Just due to that fact that I do not agree with the decisions and direction the company is actually going in," Cooper told Business Insider in February 2016. "I was representing the brand internationally and domestically as an ambassador...and I was essentially asked to no longer participate in the board meetings because I didn't agree with [Flanders'] vision for the company. You either sort of take a step back and say, 'OK, I'm going to let this happen' or you try and do something about it.' And I'm certainly trying to do something about it."
"There's nothing that I want more than for the company to be successful," he continued. "And when you have a company, and the founder is responsible for kickstarting the sexual revolution—and then you pluck out that aspect of the company's DNA by removing the nudity—it makes a lot of people, including me, sit and say, 'What the hell is the company doing?'"
The discord in the company didn't negatively affect Cooper's relationship with his father, and they remained as close as ever, "but of course it was not an easy situation for either of them," the family source says. "They continued to talk through the whole thing and Cooper was very up front with his dad about why he needed to focus on his own business, HOP [Hefner Enterprises & Productions], rather than get bogged down with the politics inside Playboy."
Hefner was, however, "definitely upset" by the dispute, as he had always envisioned working with his son and was disappointed when they split professionally. Ultimately, the father of four fully understood why Cooper did what he did, but "it was not an easy time for either of them."
"Cooper truly believed people were making the wrong decisions about the brand and were using Hef's age against him," the source said. "In the end it became so frustrating that Cooper had to leave. He just couldn't watch what was happening anymore."
All the while, as the insider noted, Hefner did have other things on his mind.
In March 2016, Crystal Harris, Hefner's wife of three years, revealed she was battling Lyme disease, a strength-sapping condition that has side effects ranging from joint pain and headaches to heart palpitations and facial paralysis. The following month, a few weeks before Hef's 90th birthday, he suffered a devastating blow when his brother, Keith Hefner, died of cancer at 87.
"They were best friends and Hef was absolutely heartbroken," another source said. "Keith was younger than Hef and yet they had the kind of relationship where Hef would always go to him if he wanted to talk something through. Once Keith passed, it just really dimmed a light in Hef's eyes. For a while he was inconsolable...and I'm not sure he ever really got over Keith's passing."
Last summer, Hefner also sold his beloved Playboy Mansion, the storied party palace that for decades served as a hedonistic beacon for Hollywood's A-list but—while still a go-to destination for celebrity-packed events—was increasingly considered a relic of another time. Cooper wasn't particularly on board with Playboy Enterprises' decision to put the mansion on the market, either, telling Business Insider, "When you talk about selling the mansion, that is something you can't take back, if somebody wants to purchase the house. It's challenging for me to talk about the decision that went into selling the house because I don't understand the logic.
"I understand the financial logic of wanting cash available, and having that to invest in other aspects of the company, but you have to understand that my point of view is very different than some of our board members and leadership in the sense that my concern is that there is a company that people care about in 15 years."
Hostess Brands heir Daren Metropoulos bought the Holmby Hills estate for $100 million, agreeing to the stipulation that Hefner be able to live there for the rest of his life—which he did. Hefner died at home on Sept. 27.
In an August interview with The Hollywood Reporter, Cooper maintained that it was physical ailments, including back pain and hearing trouble, that kept his father increasingly homebound. He still welcomed visitors, but he didn't want to be photographed out and about looking like anything less than the pipe-smoking bon vivant he had always been. "It's tough to watch him struggle, but I'm just happy it's physical and not mental," Cooper said.
Meanwhile, in a happy turn of events, Hefner was still around to see his son return to the family business. Flanders left and the company's current CEO, Ben Kohn, asked Cooper to come back in June 2016. The 26-year-old entrepreneur is now chief creative officer of Playboy Enterprises—a position once held by his dad.
Another position held by both father and son is back in effect as well: Nudity returned to Playboy in March.