'Yes, Hugh Hefner promoted sexual freedom, but what he really meant was sexual freedom for men'

To the US Postal Service, the huge, Gothic Revival-style building in which he lived is just a zip code: CA 90024. To the rest of the world, however, it's the legendary Playboy Mansion, either a sort of heavenly alternative reality staffed by scantily clad women where any and all desires could be fulfilled – or a tawdry and outmoded emblem of sexual exploitation lorded over by a dissembling, pyjama-clad sleaze-ball whose philanthropic gestures and protestations about equality and feminism weren't worth the cocktail napkin they were written on.

And it's those two conflicting views of Hefner and everything he stood for that are finding expression in the questions now being asked: was he legend or lech? Liberator or oppressor? Pioneer or pimp?

News of Hefner's death was announced on the website of Playboy Enterprises, the globe-spanning publishing and entertainment brand he founded on his kitchen table in December 1953 when he put together the very first edition of Playboy. He died peacefully, the announcement says, surrounded by loved ones, and is to be buried at Westwood Village Memorial Park Cemetery in the crypt next to the one occupied by Marilyn Monroe. He bought it specially in 1992. Monroe, of course, was the centrefold in that famous first edition.

The announcement on the Playboy Enterprises website also included a tribute from Hefner's son Cooper, the 26-year-old chief creative officer of Playboy Enterprises.

“My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom,” he wrote. “He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognisable and enduring in history. He will be greatly missed by many”.

He'll certainly be missed by his friends, his three other children and his third wife, Crystal Harris, who is 60 years his junior. But the pain they feel at his death could be assuaged to some extent by the thought of what some of them may stand to inherit – Hefner's personal fortune is estimated at anywhere between $50 and $200 million – and the knowledge that whatever else anyone says about the Playboy founder, he certainly made his mark on American life in the second half of the 20th century.

But there are others with nothing to gain who will miss him too, and who have come forward to say so. Kim Kardashian is one. She had only warm words for Hefner, tweeting: “RIP to the legendary Hugh Hefner! I'm so honoured to have been part of the Playboy team.” The Reverend Jesse Jackson is another, hailing him as “a strong supporter of the civil rights movement”, while to Paris Hilton he was a “legend” and an “innovator”. Meanwhile Jenny McCarthy, a former Playboy Playmate who later became a TV host, author and activist, wrote: “Thank you for being a revolutionary and changing so many people's lives, especially mine. I hope I made you proud.”

Revolutionary, legend, innovator, mentor. These are big words to apply to a man who made his money from peddling pictures of naked women and who appeared to use real women merely as sexual playthings. So are the valedictions actually valid?

In some respects, yes. Hefner would certainly have applied them to himself, believing as he did that he singlehandedly kick-started the sexual revolution. And it's certainly true that he gloriously and unashamedly put sex into the open through the pages of Playboy magazine. It's also true, as he often said, that he was gloriously and unashamedly fond of the act itself, just as he was condemnatory of any moral authority which sought to impose rules on human sexual activity or issue proscriptions. “I think that sexual oppression and dictatorship go hand in hand,” he once said, quite reasonably.

Less succinctly, he once had this to say about why societies need to be open about sex. “If you don’t encourage healthy sexual expression in public, you get unhealthy sexual expression in private. If you attempt to suppress sex in books, magazines, movies and even everyday conversation, you aren’t helping to make sex more private, just more hidden. You’re keeping sex in the dark. What we’ve tried to do is turn on the lights.” And as everyone knows, sex with the lights on is way more fun.

Hefner had read, digested and agreed with Betty Friedan's 1963 book The Feminine Mystique, a key feminist text. To his mind, she and he were doing the same thing – normalising women's sexuality. Predictably, then, he declared himself a feminist, most notably in a cover interview with Newsweek in 1986. For University of Chicago history professor Elizabeth Fraterrigo, author of Playboy And The Making Of The Good Life In Modern America, the magazine (and, by implication, Hefner) “stood on common ground with the liberal elements of the women’s movement”. Not exactly sisters-in-arms, but something close to it. And remember Hefner also gave space in Playboy to Ursula Le Guin, Margaret Atwood (who had several short stories published) and Germaine Greer, and he advised Helen Gurley Brown when she wanted to use Playboy as a model for a revamp of the magazine to which she had just been appointed editor – Cosmopolitan.

For Carrie Pitzulo, a history professor at Colorado State University and author of Bachelors And Bunnies: The Sexual Politics Of Playboy, Hefner had a notable role to play in promoting a woman's right to abortion too. She notes that Playboy published an article in favour of it eight years before the famous Roe V Wade court case which finally made it law in 1973, and in the months before the case it published the phone numbers of hotlines women could call to get information about safe places for abortions.

“In its heyday in the 1960s and 1970s, Playboy was supportive of mainstream liberal feminist causes,” Pitzulo told Fortune magazine as it analysed Hefner's legacy last week. “If women can have consequence-free sex, that helps the guys … But ultimately, Hefner and his editors genuinely supported this cause because they believed in personal freedoms. It’s not that there was no sexism or male privilege in Playboy, there’s just more to it than that.”

Jesse Jackson's comments about Hefner's support for civil rights carry weight as well, and are not misplaced. Hefner had long championed the rights of black Americans, as well as their achievements and their cultural contribution. The very first interview Playboy ran was written by African-American journalist and author Alex Haley, who would go on to write Roots. Its subject was iconic jazz trumpeter Miles Davis, and among its wide-ranging topics was the issue of race and racism. Haley would also interview George Lincoln Rockwell, founder of the American Nazi Party (Rockwell only agreed to do the interview if Haley could prove he wasn't Jewish) and Playboy itself would later run interviews with Muhammad Ali, Martin Luther King Jr, Malcolm X and Eldridge Cleaver, leader of the Black Panthers. In 1959, Hefner organised the Playboy Jazz Festival in Chicago and donated the first day's takings to the National Association for the Advancement of Colored People, one of America's key civil rights organisation.

Hefner was even an early advocate of gay rights and gay marriage. “Without question, love in its various permutations is what we need more of in this world,” he said in 2009. “The idea that the concept of marriage will be sullied by same-sex marriage is ridiculous. Heterosexuals haven’t been doing that well at it on their own.”

Over 50 years earlier, in 1955, he published a sci-fi story in Playboy by Charles Beaumont, a writer on hit TV series The Twilight Zone. Called The Crooked Man, it was set in a dystopian future in which heterosexuals were persecuted by homosexuals, the point being to highlight the absurdity of anti-gay prejudice in the real world. The story was judged so controversial by Esquire that they refused to run it. Hefner had no such qualms and then defended it in the teeth of an avalanche of complaints by writing: “If it was wrong to persecute heterosexuals in a homosexual society, then the reverse was wrong too.”

BUT despite all this it's hard not to conclude that the sexual freedom Hefner endorsed, and which his son cites as being one of his greatest contributions to American culture, was pretty much a one-way street. Yes, Hefner promoted sexual freedom, but what he really meant was sexual freedom for men. For the women dressed up as bunny rabbits in one of the many Playboy night clubs – there were nearly 50 in all and yes, even Portsmouth had one – or corralled in the Playboy Mansion where they were given an allowance, made to adhere to strict rules and expected to be at Hefner's beck and call, freedom was a loaded term.

“Everyone thinks that the infamous metal gate was meant to keep people out,” wrote former bunny Holly Madison in her 2015 memoir, Down The Rabbit Hole: Curious Adventures And Cautionary Tales Of A Former Playboy Bunny. “But I grew to feel it was meant to lock me in.” Madison even considered suicide at one point.

Similar sentiments were echoed half a century earlier by one of Hefner's fiercest critics, the feminist author Gloria Steinem. For a two-part 1963 expose published in Show magazine, she adopted the name Marie Ochs, squeezed into a bunny outfit and went undercover as a waitress in a Playboy club. She found the conditions harsh and the treatment of women difficult to square with any notion of emancipation.

“I think Hefner himself wants to go down in history as a person of sophistication and glamour," she said later. "But the last person I would want to go down in history as is Hugh Hefner.” Naturally, he responded. “Women are the major beneficiaries of getting rid of the hypocritical old notions about sex,” he said. “Now some people are acting as if the sexual revolution was a male plot to get laid.”

Back in the 21st century, others have equally harsh things to say about Hefner. When it comes to that pioneer or pimp question, British journalist and critic Suzanne Moore is very much on the side of pimp – and she once said so in print. Hefner's response was to threaten to sue her. “To me this was not even controversial; it was self-evident,” she wrote last week, recalling the phone call she received from his lawyers and how sorely tempted she was to test her claim in court. “Now that he’s dead, the disgusting old sleaze in the smoking jacket is being spoken of as some kind of liberator of women,” she continued. “I don’t really know which women were liberated by Hefner’s fantasies. I guess if you aspired to be a living Barbie it was as fabulous as it is to be in Donald Trump’s entourage.”

Sarah Vine, the journalist wife of politician Michael Gove, went even further. “For those of us unwilling to inject our bodies with silicone, or ill-equipped for posing in a thong, or simply reluctant to lead a life as a perpetual courtesan, Hefner's legacy is one of the most toxic in human history,” she wrote. “No man ever did more than Hugh Hefner to popularise the sexual exploitation of women. He paved the way for the 'pornification' of day-to-day society and for the widespread notion – in itself depressing enough, but in recent years rendered even more dangerous by the rise of extreme Islam – that all Western women and young girls are promiscuous moral degenerates, neither deserving nor desirous of respect.”

Hefner would have a come-back for that, no doubt. He had heard similar arguments for decades. He isn't here to provide one, but his words are. “I would like to think that I will be remembered as someone who had some positive impact on the socio-sexual values of his time,” he once said. “And I think I’m secure and happy in that.”

He might be, but nobody else is. The questions remain and the chances are they'll never be answered to everyone's satisfaction. All we can say for certain is this: Hugh Hefner died the way he lived – with his pyjamas on – and he'll be dividing opinion for many years to come.