Typically, when we think about big divorce settlements, it’s the woman making off with the cash. But that’s not always the case. When the lady is the breadwinner of the family, sometimes the man is entitled to a bigger slice of the pie. In this feature, we’ll examine ten of the biggest male divorce settlements of all time.
Rene Elizondo, Jr.
Life in the Jackson family isn’t particularly normal, so it’s unsurprising that when Janet Jackson fell in love with Mexican-American songwriter Rene Elizondo, Jr., she kept it secret from her crazy relatives. The pair were married in 1991 without any fanfare, but over the course of their 13-year marriage, they slowly but steadily fell out of love. When they finally split up for good in 2000, Elizondo sued Jackson for spousal support, claiming that he’d been forced under duress to sign a prenuptial agreement. At the end of all the messy courtroom action, Elizondo came away with an estimated $10 million in cash.
Sure, British director Guy Ritchie had a well-established career before he married Madonna, but the Queen of Pop was obviously several levels above his pay grade. When the pair split in 2008, after being married for eight years, the love was obviously gone between them. But under joint property agreements, Ritchie was entitled to a serious chunk of Madonna’s material wealth. He walked away with a meaty $92 million worth of cash and property, one of the biggest settlements of all time.
Liz Taylor married eight times in her lifetime, to men from all over the social spectrum, but one of the most perplexing was her final take on matrimony in 1991 to construction worker Larry Fortensky. The pair were wed at Michael Jackson’s Neverland Ranch, which is never a good omen, but managed to stay together for five years. Interestingly enough, Fortensky had signed a prenup which stated that he’d get a million dollar payout in case of divorce … but only if the marriage lasted five years or more. After the split, the pair remained in contact, and when Taylor died in 2011, she left him an additional $800,000 in her will. Now that’s a double payday!
Jim Threapleton met actress Kate Winslet in 1998 on the set of the low-budget drama "Hideous Kinky," and the pair quickly fell in love. At the same time, Winslet was earning huge amounts of money from the success of "Titanic," so her new husband’s career didn’t need to keep pace. The pair had a daughter in 2000, but it wasn’t enough to make the marriage work and they divorced the following year. Because they had put no prenuptial agreement in place, their property was divided equally, with Threapleton taking away $4 million that he sure didn’t earn. The pair are still friends, however, and raise their daughter amicably.
When sitcom star Roseanne Barr fell madly in love with Tom Arnold in 1990, her attorneys recommended (begged) that the couple sign a prenup before they tied the knot. Barr was so infuriated by the suggestion that she fired her lawyer, but just four years later, she and Arnold acrimoniously divorced. Arnold’s drug and alcohol addiction had pretty much made their marriage unsustainable, so it’s not terribly surprising. California’s community property laws let Arnold start his newly single life with a cool $50 million in his pocket, and he has openly carried on and prospered with it ever since.
Los Angeles plastic surgeon Harry Glassman had a successful, thriving practice when he got divorced in 2006, but his wife, former "Dallas" star and QVC pitchwoman Victoria Principal, was on a much higher level. The couple had established a prenup before they wed in 1985, but almost 20 years of marriage made enforcing it incredibly difficult. Principal and Glassman had a combined net worth of over $50 million, most of which she earned, but at the end of the proceedings, the pair split everything down the middle, letting Glassman get away with $25 mil.
A marriage doesn’t have to last a long time to give a guy a big payoff at the end of it. Cris Judd married Jennifer Lopez in September 2001 after a whirlwind courtship. The actor/dancer met Lopez in Spain when he was hired to direct her video for “Love Don’t Cost a Thing,” and they had instant chemistry. Unfortunately, instant chemistry isn’t enough to keep a marriage going, and they split up in June 2002. Judd took away a massive settlement from Lopez, with reports saying that he got about $14 million for nine months of matrimony.
Katie Price is one of Britain’s most attractive glamor models, but that didn't seem to help her much in the courtroom. Her marriage to reality TV star Peter Andre, whom she met on "I’m a Celebrity … Get Me Out of Here!" lasted only three and a half years. The pair split due to a number of small squabbles, but Price’s net worth was significantly higher. Andre settled for exactly half of the money the couple had made during their marriage, which was a very tidy $9.6 million. He didn’t get anything Price had made before the wedding, but he probably wasn't all too worried about it at that point.
When Kirstie Alley and Parker Stevenson split up in 1997, Alley was still hot after the end of "Cheers," while Stevenson’s career had stalled. The pair had been married for 14 years and had two children, but things got ugly in the divorce right away. Stevenson wanted to split under California’s divorce laws, which favored community property, while Alley wanted to do it in Maine. The pair had an over-the-top Hollywood lifestyle featuring a massive mansion, multiple nannies and a zoo’s worth of exotic animals. Stevenson ultimately won out, and took away $6 million.
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No man in recent pop culture history has gotten lucky quite like Kevin Federline. The backup dancer and aspiring rapper roped in pop princess Britney Spears in 2004, quickly knocking her up with a pair of kids and basically ruining her career. Spears eventually came to her senses in 2006 and cut K-Fed loose, but the process wasn’t easy. The duo argued over money, and even with Spears having an ironclad prenup in place, K-Fed still walked away with a cool million, plus an additional $20,000 per month in child support. Since then, Federline’s main occupation has been appearing on celebrity weight-loss shows.