Hugh Hefner Divorcing After 11 Year Separation 2

Hugh Hefner and Kimberly ConradPlayboy founder Hugh Hefner filed for divorce from his wife, former Playmate Kimberly Conrad, last Friday in Los Angeles. They’ve been married since July 1989 but separated since 1998

. Since the separation, Conrad and the couple’s two sons lived in a home next door to the famed Playboy Mansion in L.A.

Hefner says he paid Conrad $40,000 a month pursuant to a prenuptial agreement following their separation and claims that, in total, he gave her close to $12 million since 1998. (They apparently had a postnuptial agreement as well.) He filed for divorce after Conrad sued him recently for $5 million stemming from the sale of the home Conrad was living in.

Hefner told the media: “I would’ve been happy to divorce her when we separated, but she wanted to remain married for our boys.” The couple’s boys, Marston and Cooper Hefner, are now both in college.

He asked the court to set spousal support for Conrad at $20,000 a month. His income and expense statements reveal that he makes almost $300,000 a month – from Playboy salary, investments, Social Security and other income. He lists his assets at about $43 million. Hef wants the monthly payments to end in two years, or after a trial on the couple’s divorce is held, whichever comes first.

Hef claims that he was “faithful” during the time he and Conrad were together, but says she cheated on him “early in the relationship.” He has lived with three girlfriends at the Playboy Mansion since 2001. Their relationship has been the subject of the E! show “The Girls Next Door.”

Hefner founded Playboy magazine in 1953 and has two adult children from a first marriage.

I don’t know what Conrad intends to do going forward but it seems unlikely that she could successfully challenge the prenuptial or postnuptial agreements (unless she has newly-discovered proof of fraud on Hef’s part). She has lived by the terms of the agreements for over a decade. It is doubtful that a court would now let her argue that those same terms are unconscionable in some way.

Without knowing the exact claims made in the civil lawsuit, Conrad may have a better shot of getting more money out of her estranged husband in that court than in family court.