Hugh Hefner dead: The 'devastating' marriage betrayal that turned Playboy founder into a serial ladies man

The infidelity would forever skew his view on sexuality 

Sarah Young
Thursday 28 September 2017 12:47 BST

A man who became famous for his hedonism, Hugh Hefner claims to have slept with more than 1,000 women with a stable of girlfriends less than a third of his age.

But it turns out that the silk-robed, pipe-smoking Casanova’s Playboy lifestyle may have been sparked by the "devastating" betrayal of his first wife.

Hugh – who died yesterday age 91 – vowed to ‘save himself’ for childhood sweetheart Mildred ‘Millie’ Williams until they got married. But just days before their wedding, Williams revealed that she had slept with someone else.

“I had literally saved myself for my wife, but after we had sex she told me that she'd had an affair. That was the most devastating moment in my life,” Hefner once said.

Despite the revelation, the pair got married in 1949 and went on to have two children – daughter Christie Hefner, born in 1952, and son David, born three years later.

However, the betrayal loomed over their marriage and Williams gave her husband permission to sleep with other women; a decision that would forever skew his views on the institution and sexuality.

After 10 years the marriage came to an end but with the successful launch of Playboy in 1953, Hefner’s lavish and lecherous lifestyle was only just beginning.

The serial ladies’ man who became famed for hosting decadent parties at his luxurious Playboy Mansion, has dated a parade of high-profile women over the years but following a stroke in 1985, at the age of 59, Hefner settled down and married Kimberley Conrad, who was 26 years his junior.

Hugh Hefner poses with Playboy Bunnies at one of America's chain of Playboy clubs in 1962, a year before Ms Steinem went undercover (Helmut Kretz/Getty Images)

Although the couple went on to have two sons, he continued to live with multiple girlfriends until their marriage ended 11 years later.

Following a brief stint living with lovers Holly Madison, Kendra Wilkinson and Bridget Marquardt, the Playboy Tycoon married once again with Crystal Harris – who was 60 years younger – set to become his third and final wife.

Playboy bunnies at Hefner's mansion in Los Angeles

Following his death from natural causes, Hefner was survived by his partner and four children but it is reported that, in light of a prenuptial agreement, she will receive nothing of his multi-million dollar fortune.

Join our commenting forum

Join thought-provoking conversations, follow other Independent readers and see their replies


Thank you for registering

Please refresh the page or navigate to another page on the site to be automatically logged inPlease refresh your browser to be logged in