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Hugh Hefner’s wild pedigree and scandals as late star becomes grandpa again

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It’s been almost five years since Hugh Hefner died at the age of 91, but the Playboy mogul is still making headlines and sparking debate.

As the world re-examines the late star’s legacy – thanks to the shocking Secrets of Playboy docu-series – the magazine founder’s youngest son has become a father again.

Cooper Hefner and his wife, Harry Potter actress Scarlett Byrne, welcomed twins into the world earlier this month – and announced the happy news via Instagram on Tuesday.

As new generations of Hefners continue to be born, let’s take a look at Hugh’s complicated and wild family tree…

Conservative beginnings

The Playboy founder may have liked to think of himself as a liberal and self-proclaimed leader of the free love movement, but the late star’s family tree begins with his two conservative parents.







Hugh Hefner – pictured with widow Crystal – passed away on September 27, 2017
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The late star’s parents, Grace and Glenn Hefner
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Born in Chicago in 1926, Hugh was the eldest of two children born to his father, Glenn Lucius Hefner, an accountant, and his mother, Grace Caroline (Swanson) Hefner, a homemaker and teacher.

Through his father’s line, the late star was a descendant of Plymouth Governor William Bradford – an English Puritan separatist originally from Yorkshire.

“My parents were raised strictly Prohibitionists. They were very good people with high moral standards – but very downtrodden,” Hugh told THR in 2011.







Hugh and his younger brother Keith, who passed away in 2016
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“There were no hugs and kisses in my house.”

Hugh’s younger brother Keith later became part of the Playboy empire – training rabbits and recruiting new models.

Political cousins

Throughout his life, Hugh often became involved in many political causes and campaigns – perhaps something he was always destined to do thanks to his family connections.

Before the 2004 US elections, it became known that the American magazine publisher was a distant relative of the two presidential candidates George W. Bush and Senator John Kerry.







Hugh and the former US President were believed to have never met
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The Playboy founder was much happier to hear he was distantly related to Senator John Kerry
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After learning he was the ninth cousin of both men, proud Democrat Hugh joked, “Well, I feel closer to Senator Kerry.”

He continued to CBS News, “You know I’m an 11th generation direct descendant of William Bradford, who came over on the Mayflower, a direct descendant of a Puritan. I suppose it’s not a huge surprise, but it’s certainly unique to be related to both candidates.”

betrayal of virginity

In 1949, Hugh married for the first of three times — he married Millie William, a Northwestern University classmate who would father two of his children during their 10-year union.







Hugh and his first wife Millie
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Hugh lost his virginity to his first wife, although she admitted to cheating on Star while he was in the army.

“I was literally saving myself for my wife, but after we had sex she told me she was having an affair,” he told the Daily Mail in 2007.

“It was the most devastating moment of my life. My wife was more sexually experienced than me. After that, I always felt like the other guy was in bed with us too.”







Hugh Hefner and daughter Christie Hefner
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Married for decades, they welcomed daughter Christie and son David into the world together before their split.

Not much is known about Hugh’s eldest son – the 57-year-old chose to stay out of the limelight and instead found a career away from the Playboy empire.

However, Christine became president of the Playboy corporation in 1982, and chairwoman and chief executive officer in 1988.

“Well, I commented on that [if] Christie didn’t exist, our advertising department might want to invent her,” Hugh told the New York Times in 1979.







Hugh and then-president of playboy empire Christie in 1982
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“She is ideally suited, both symbolically and factually, to the role she plays in the company and the role she hopes to play in the future.”

Speaking about her role at the magazine, Christie added, “I’m a lot more excited about changing what’s going on in Cosmopolitan and Family Circle magazines than I am in Playboy about roles for women.”

second wife

Hugh was married for a second time in 1989 – he married 26-year-old Kimberley Conrad when he was 63.

The couple had met at a Playboy shoot two years earlier and later had sons Marston and Cooper.







Hugh and model Kimberley met thanks to his magazine empire
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Hugh and son Marston attend FilmDistrict’s world premiere of The Rum Diary
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Marston controversially lived with his father in the Playboy mansion for the first eight years of his life — something he later had seemingly conflicting feelings about.

“Well, seeing naked people occasionally as a 15-year-old boy, that’s just the lifestyle, growing up in his shadow as Hugh Hefner’s son,” he recalled to GQ in 2008.

“It’s not a boo-hoo sob story. But it’s not the same as any other child. … It’s easy to tell who wants to be your friend and who doesn’t for these reasons. People find out and they’re like, ‘Oh my God, Hugh Hefner is your father. You’re a god.” And I’m like, ‘Okay, I’m a god. Yes. I am a god.'”







Marston is no longer in the public eye
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Marston was often thought of as “Hef Junior” and had been brought up to follow in his father’s footsteps, but faded from the limelight after he was sentenced to 52 weeks in a 2012 domestic violence scheme.

Kimberley and Hugh eventually split in the ’90s, but they seemed to remain on good terms — as the mother-of-two moved into a $7million home next door to the infamous Playboy mansion.

Hugh even called his ex-wife “the love of my life” when announcing their split, and the couple remained legally married until he finally filed for divorce in 2009.






The couple’s divorce was not finalized until years after their initial split

The official split came after Kimberley sued her ex, claiming he owed her millions as a result of their prenup

The divorce was finalized in 2010 and it was reported that the former couple had agreed on a confidential ownership arrangement.

Third and last wife

Hugh’s third and final wife was Playmate Crystal Harris, who became his widow after his death in 2017.

The couple tied the knot on New Year’s Eve 2012, but not before major drama – when their original wedding was canceled at the last minute.

Crystal, then 26, left Hugh, 86, just days before their wedding in June 2011.







Crystal was married to the Playboy tycoon at the time of his death
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The canceled wedding wreaked havoc in Hugh’s business too – as the July issue of Playboy starring Crystal as ‘Mrs Crystal Hefner’ has already hit the shelves.

It appears the model had a change of heart, and the couple reconciled and eventually exchanged vows in an intimate ceremony on December 31, 2022 — they remained married until Hugh’s death in 2017.

“I felt how much he loves me. I loved him so much,” Crystal People said shortly after her husband’s death.

She added, “I will be eternally grateful to have been by his side, to have held his hand and to have told him how much I love him.”

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