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The two married in 1949 and had two kids together: Christie, who was born in 1952, and David, born in 1955. He later said that hearing that his wife had strayed from their marriage was the most devastating moment of his life, according to reports.In an attempt to make up for the infidelity, she allowed him to sleep with other women.Carrie Leigh (1983-1988)Leigh became Hefner’s first long-term girlfriend in the years after he and Benton split.Leigh lived with him in the Playboy Mansion for five years before she broke up with him and left.Hugh Hefner was surrounded by his third wife, Crystal, and his three sons, Cooper, David, Marston, and daughter, Christie, when he passed away peacefully at the Playboy Mansion Wednesday.The 91-year-old founder of Mildred Williams (1949-1959)Hugh Hefner and Mildred Williams met in college at Northwestern University. Army, Williams had an affair that she admitted to him when he returned.They had a wedding planned for June 2011, but five days before the nuptials, she broke off the engagement.That same month, she was on the cover of Playboy to announce “Mrs.

It's safe to say Hefner made Pamela Anderson a household name when he featured her on the October 1989 cover, and many people would go on to say that she was one of his favorite models of all time.

Following Hefner’s passing, Wilkinson tweeted “Can’t really put in to words how I really feel.”, Hefner invited twins Kristina and Karissa Shannon to move into his mansion and be a part of the show. He reportedly broke up with them after finding out they had younger boyfriends come inside the home.

It's no secret Hugh Hefner was a multi-millionaire.

Cast Hefner was known for dating many women at once.

At one point, he reportedly dated as many as seven women at a time, with the ladies living in the mansion with him.

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She said they were left on her side of the bed they previously shared and that it stated that after death tax, Hef's fortunes "would be divvied up starting with roughly 50 percent to his charitable foundation and the bulk of the remainder divided evenly between his four children: Christie, David, Marston, and Cooper."She also wrote that the will stated that $3 million would be bestowed to her at the time of Hef's death, "provided I still lived at the mansion." Madison said she did not want the money and was offended, writing, "Did he really think he could buy me? After Madison's memoir was published, the Playboy founder said in a statement, "Over the course of my life I've had more than my fair share of romantic relationships with wonderful women.

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