11 Most Infamous Gold Diggers

The gold digger has been a phenomenon that has existed since the advent of the monetary system.  We are not referring to the men who toiled away in the mountains in search for literal gold…We’re talking about the “I ain’t sayin she’s a gold digger, but she ain’t messin with no broke….” type of gold digger.  It has always been common for wealthy aristocratic women to find other rich families and “marry into wealth”.  This was done in the past to make sure that wealthy families kept their social status.  Yet still, even back then, it was possible for women to use marital law in their favor and reap financial gain off of an impending divorce.

The modern day version of that is different in that it’s now rock stars, athletes and internet businessmen who have to worry about these sultry women seducing them and cleaning them out for millions.  Young sports stars have to actually go through training when they enter the league on how to avoid potential women using them to get pregnant and then suing for child support for the rest of their lives.  There are advisors for this kind of thing, because it is potential big business.

Modern law requires the issuing of a prenup in order to make sure that you don’t lose all your money after the marriage ends.  But there are still slippery ways of going around this legal process.  A prenuptial agreement involves the dividing up of assets in an agreed upon way before the marriage begins, if the marriage ends in divorce.

Songs, movies, and plays have been written on this dour subject because of the very fact that it hits all the right chords with those who fear for their financial future.  There are those who seemed to have started with good intentions, only to descend into the gold digger pantheon after leaving their rich celebrity spouse crippled.  Let's take a look at some of the most notable and famous examples of these treacherous encounters.


11 V. Stiviano

V. Stiviano recently came to the public’s attention by outing Donald Sterling as a racist.  Something that was already known to many was finally cemented after we all heard the recording that was leaked to TMZ.  Before bestowing that gift upon us, she was milking Donald Sterling out of millions of dollars worth of gifts, according to court documents filed by Donald Sterling’s wife.  Donald Sterling bought Stiviano her own place worth an apparent $1.8 million.  He bought her cars (a Ferrari and two Bentleys).  And she had some sort of allowance worth many more hundreds of thousands of dollars.

10 Heather Mills

The woman with the wooden leg, who broke Paul McCartney’s tender heart.  She took down a living legend and one of the most beloved musicians of all time.  Once it leaked in the press that the couple was getting a divorce, Heather started to receive harsh criticism for seemingly duping Mr. McCartney.  Their legal battle lasted a long time, tarnishing her image in the process.  She wound up with $50 million when all was said and done.

9 Kimora Lee Simmons

Kimora Lee Simmons married the Uber-wealthy hip-hop icon Russell Simmons.  Russell Simmons is the founder of Def Jam Records and owns several other companies as well.  She didn't exactly take all his money after the divorce, but what she did get might end up proving to be far more profitable.  Instead, she took over his fashion label empire Phat Farm.  She continues to run the company and even made a reality TV show revolving around her new CEO position.  Basically, a very creative way of making the most out of divorcing your very successful husband.  She is now married to an investment banker.

8 Anna Nicole Smith

Probably the most obvious case of gold digging imaginable.  In 1994, 26-year old Anna Nicole Smith married 87 year J. Howard Marshall, an oil tycoon.  When the old man died, he actually left her nothing in his will.  She went to court, obviously, and fought legal battles for years trying to get close to half a billion dollars.  She brought the suit against Marshall’s son and the two engaged in a seemingly never ending dispute.  The case got as far as the Supreme Court.  Smith died in 2007 while the legal war was still going on.

7 Kevin Federline

The infamous former husband of Britney Spears was a dancer and already married when he met the pop star in 2004.  The two wed in July 2004 and had a two-year marriage before Spears threw in the towel.  When the divorce papers were finally settled, Federline received custody of the kids and was due to receive $20,000 per month in child support payments. That’s a pretty decent sum for anyone to live on.  After his marriage to Spears, he had a forgettable reality television career and terribly reviewed music career.

6 Rachel Hunter

At 17 she was already a model and turning down big contracts like posing for Playboy.  She met Rod Stewart, the celebrated rock star, at age 21 and the two were quickly married.  It wasn't a total train wreck, as the marriage lasted nearly sixteen years.  But it must be said that after she walked away with $66 million from the divorce, she was quickly engaged to an NHL player 13 years younger than her.  Her engagement to Jarret Stoll didn't last, however.  But that giant divorce settlement still makes her one of the most desirable cougars around.

5 Gabriel Aubry

Another golddiggin’ fella!  Aubry is a male model that works for some of the biggest names in the fashion industry including Tommy Hilfiger, Versace, and Calvin Klein.  He married the breathtaking Halle Berry and the two had a whirlwind romance before they wed in 2006.  After the divorce, the couple engaged in a bitter custody battle.  Berry requested custody of their child and wanted to move to France with her new man, actor Olivier Martinez.  Aubry demanded custody and sought a whooping $20,000 per month to maintain the lifestyle that “their daughter was accustomed to”.

4 Oksana Grigorieva

Oksana Grigorieva is a Russian songwriter and pianist, who became involved with Mel Gibson and bore his child in 2009. During their tense breakup, she was actually offered around $15 million from Gibson’s legal team.  She refused and this was ultimately her downfall, as she would end up with a mere $750,000.  One of her friends later told a journalist that she was always on the lookout for her next “sugar daddy” well before she met Gibson.  The infamous tapes of Gibson yelling at her over the phone went viral.  This added more fuel to the “Mel Gibson has a few screws loose” camp.

3 Ivana Trump

Ivana and Donald Trump were married in 1977 and divorced in 1992.  You can’t exactly describe Ivana as a golddiger because it was rumored that The Donald was having an affair with Marla Maples, a former beauty queen.  She makes the list because of the sheer numbers involved.  It was a closed case to the public, but rumors got out of the potential settlement. Ivana got over 20 million dollars, a $14 million family estate in Connecticut, and $350,000 in annual alimony.

2 Sarah Ferguson

1 Amy Irving

Amy Irving is an actress who married Steven Spielberg in 1985.  The couple was notoriously on and off and before they were married, Willie Nelson apparently broke the two up for a while. That little romance cost Irving the part in the Indiana Jones film Steven Spielberg was shooting at the time.  They eventually rekindled and wed. The two were married only 4 years before getting a divorce. She received a settlement of close to $100 million.  The story goes that Steven Spielberg actually wrote up a prenup, but it was written on the back of a napkin.  One wonders how that didn't hold up in court.

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