"A feminist? He wouldn't go that far..."

As Hugh Hefner's family auction off his personal effects, Celia Walden discusses his legacy with his daughter, Christie

When I first met Hugh Hefner 11 years ago, he was wearing his trademark bespoke black silk pyjamas. Whether the very same pair will go under the hammer tomorrow (Friday) is possible but unlikely, says his daughter.

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"My father had so many pairs," laughs Christie Hefner, who will be there to witness some of her father's most personal possessions go up for auction this week in Los Angeles.

"Too many to count. It would have been like counting jelly beans in a jar, they were all the colours of the rainbow."

The August night that my husband took me to one of Hefner's infamous Midsummer Night's Dream parties at the Playboy Mansion, he paired his black pyjamas with matching slippers and his signature scarlet silk smoking jacket - now on offer for a very reasonable US$3,000 (NZ$4378). It is being sold alongside everything from a 34in fishnet-stockinged leg lamp that once stood on his nightstand (US$75-$150) to a first edition of F Scott Fitzgerald's The Great Gatsby (US$3,000-$4,000), a portable typewriter on which the first issues of his magazine were bashed out (US$2,000-$4,000) and the very first 1953 issue of Playboy printed, featuring Marilyn Monroe on the cover (US$3,000-$5,000).

"What are you doing bringing your wife?" gawped David Hasselhoff when he saw my husband Piers - a fellow judge on America's Got Talent at the time - arrive at the mansion. "You don't take sand to the beach." Given the dress code was "lingerie or less", most of the female guests had turned up in far scantier scraps than they'd wear to the beach - some even opting to paint their underwear on. When I tracked the magnate down to a Bedouin tent nestled deep in the gardens of the five-acre estate, I found him to be surprisingly quick and charming - with the face of a tom-cat who just keeps on getting the cream.

I met the Hef once more before he died at the age of 91 last year. It was a week before his third wedding to the then 24-year-old Playmate Crystal Harris - and once again he didn't disappoint.

"A stag night?" he repeated in incredulous tones when I asked whether he was planning to have one. "Young lady, I've been having a stag night for the past 50 years."

Hefner built Playboy into a multi-million dollar business. Photo/Getty Images.
Hefner built Playboy into a multi-million dollar business. Photo/Getty Images.

For many, Hefner was just a pantomime figure with a harem of blondes and it's easy to forget how this whip-smart and well-read son of two teachers turned the NZ$745 borrowed from his mother into a global business valued at NZ$251 million just seven years ago. So busy was he building his empire, however, that Christie, now 66, "didn't see a lot of him growing up. My parents divorced when I was very young, so for years I saw him on his birthday, my birthday and Christmas.

"But then when I was in high school, we began to talk a lot more as adults, and we would have these great chats about religion, politics and the world. I've often thought that one of the most defining qualities about him was this boyish wonder," she smiles.

In the last decade of his life her father chose to celebrate his birthday in the same way every year, she tells me.

"He and all his friends would dress up in white dinner jackets, the mansion's dining room would be turned into a 'Rick's Café', and we would all watch Casablanca."

Christie - a former CEO of her father's company for 20 years - only found out after he had died that he wanted all his personal effects to be auctioned off, with the proceeds going to the Hugh M Hefner Foundation. But before Julien's Auctions spent 60 days clearing the Playboy Mansion, Christie took her younger brother David, 63, and two half-brothers, Cooper, 27, and Marsten, 28, around the estate so that they could all take anything with particular meaning before it was sold off. One item with special significance for Christie was her father's copy of Fahrenheit 451 by Ray Bradbury, which was first published as a short story in Playboy.

"The inscription reads 'To Hef, who published this when almost no one else would'," she tells me. "And because I know how much he battled censorship throughout his life, that's deeply significant to me."

One of my favourite Hefner quotes is: "I want to live in a society in which people can voice unpopular opinions, because I know that, as a result of that, a society grows and matures."

As president of the foundation - which honours individuals like journalists and whistle-blowers at the First Amendment Awards, supports civil rights and funds research into sexual health and drugs - Christie will plough the proceeds into causes her father passionately believed in.

I wonder whether she ever feels grateful that her father never witnessed the way social media has ended up closing down debate and making the world, in many ways, feel smaller than ever.

"We're now wrestling with the cultural imperative of learning to be respectful of differences, while not losing the power of freedom of expression," she agrees - adding that the puritanism we've seen come back with such force "is something my father was very strongly against. He believed that love, romance and sexuality were humanising forces and that society was not improved by suppressing them."

The countries that suppress them also tend to repress women, Christie points out. "And my father felt the ideal society is one that embraces sexuality as well as women's rights."

She can't quite hold back a smile when I ask whether Hef was a feminist ("I don't know if he would say that, but he would certainly say that he was a humanist who believed in equality"), but when it comes to the MeToo movement, Christie is in no doubt that "my father would have been very much on the side of the women.

I know he was deeply disappointed to find out what Bill Cosby had been engaged in, because they knew each other as friends. As an opponent of oppression and abuse of power, my father would absolutely have thought MeToo was a force for good."

Hefner's daughter Christie said he was deeply disappointed by the Bill Cosby scandal. Photo/Getty Images.
Hefner's daughter Christie said he was deeply disappointed by the Bill Cosby scandal. Photo/Getty Images.

With her tenure at Playboy behind her and Cooper now the chief creative officer, Christie is reluctant to talk about the future of the company her father founded almost 70 years ago. But one thing she would like to see in the magazine's pages and elsewhere "is more expressions of women's view of what is romantic and sexy. So that women wouldn't just be objects of desire, but desiring human beings.

"Right now, pretty much the only form of expression for women's erotic fantasies are romance novels, and perhaps that contributes to women's resentment that they're always the only ones being looked at," she says. There will be poignant moments at tomorrow's auction, Christie accepts, "but mostly it'll be a celebration of my father's life."

His other moving final act is being laid to rest in the crypt beside Marilyn Monroe's in LA's

Westwood Village Memorial Park cemetery. "Because he never did get to meet her. 'And this way,' he'd say, 'I get to spend eternity lying beside her.' "

The auction will take place on Nov 30 and Dec 1 at Julien's Auctions, and live online at juliensauctions.com

- Telegraph Media Group