24 Celebrity Gold Diggers That Struck It Rich

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For too many people the thought of becoming rich and never having to work again sounds like an absolute dream: so much so that they’ll stop at nothing to achieve it. While some dream of becoming rich by earning it through long hours and hard work at the office or by inventing some kind of highly sought after super-product, there are those who would just as happily accept a handout; perhaps the lowest of the low, however, are those who made their money at the expense of a wealthy spouse, especially after a particularly nasty divorce.

As an age old tradition, gold digging is a means of becoming rich by earning the love (or lust?) of someone wealthy (usually though good looks or manipulation), and then sticking with the marriage just large enough to take it to the bank; after the romance is officiated, the gold digger (who usually never loved their wealthy spouse to begin with) often vanishes: taking at least half of their partner’s amassed fortune. While gold digging isn’t an honorable method of becoming rich, it has continued to work time and time again, and as a result has created an immense paranoia amongst the wealthy.

But which celebrity gold diggers have been the most successful in terms of gaining both fame and fortune? Here are the top 24 biggest celebrity gold diggers that kept their mind on the money and the money on their mind.

#24 – Oksana Grigorieva (Mel Gibson)

Oksana-Grigorieva
Oksana Grigorieva is a singer, songwriter, and musician that hails from Russia, but if you recognize her name it won’t be because of her career: it’ll be because she was dating Mel Gibson. Gibson wasn’t the first star that Ms. Oksana tried to wrangle: her first target was Timothy Dalton, but after popping out a kid she figured there was bigger fish to fry and more money to be made. Grigorieva and Gibson only dated for one year before they were splitting up, and of course that was long enough for her to start trying to get her hands on Mel’s cash.

Gibson did the amiable thing and offered Oksana fifteen million dollars to walk away: after all they had a kid together and Gibson might be many things (an anti-Semite being among them), but he refused to be a father that wouldn’t provide for his kid; she decided that his offer wasn’t significant enough and decided to take it to court instead. When the judge looked over Grigorieva’s case it was quickly decided: she was to receive $750,000 and a house she could reside in until the kid turned eighteen; sometimes it’s better to take what you’re offered rather than pressing your luck!

#23 – Amy Irving (Steven Spielberg)

Amy Irving earned a fair bit of fame during the 1970s with her Academy Award nominated role in “Yentl,” as well as a few other big roles afterwards; her fame grew immensely while she was “coincidentally” dating Steven Spielberg. Back then Spielberg wasn’t quite the massive name he is now, and Irving (for some reason or another), had a fling with Willie Nelson just before Spielberg made it into the big times.

During their separation, as Irving’s stock plummeted and Spielberg’s began to rise at a rapid rate, Irving became increasingly desperate to recapture her beloved bankroll. Irving was in line to get the role of Marion in the huge blockbuster, “Raiders of the Lost Ark,” but Spielberg threw her aside after the split as payback; although the two eventually got back together, Irving made $100 million when they divorced: Spielberg thought he had a pre-nup, but the fact that it was written on a napkin voided its validity in court. Whoops! Who taught you contract law, Steve? E.T.?

#22 – Shawn Southwick (Larry King)

Shawn-Southwick
The biggest guy to ever step onto the television set is probably Larry King: almost every major T.V. personality thanks him endlessly for the inspirations he provided them while they were still honing their craft. King has become quite wealthy over the years, and it didn’t take long for some doe eyed vixen to start planting the seed of love in Larry’s mind; a beautiful blonde named Shawn soon roped him into marriage, and it certainly turned heads when it was revealed that she was 26 years younger than he was.

Shawn eventually filed for a divorce from Larry, but after discovering how little she’d be receiving (probably due to Larry’s past bankruptcies) she miraculously discovered the error in her ways. King was happy to take her back because (let’s be honest here) it isn’t easy to get involved in the dating scene when you’re as old as he is. The Kings are still married after eighteen years and it doesn’t look like that status will be changing any time soon, but one can’t help but wonder with her husband being 81 years old and all that Shawn might be crossing her fingers for a “till death do us part” moment to give her a nice retirement.

#21 – Anna Nicole Smith (J. Howard Marshall)

The life of Anna Nicole Smith was a rollercoaster ride which met a tragic ending. When Smith was only 24 years old she was just an unknown stripper struggling to get by; J. Howard Marshall, on the other hand, was a billionaire in the oil industry, and when the two met, she knew she had an opportunity that was too good to pass up: the only problem about Marshall was that he was darn near 90 years old at the time.

It was pretty obvious to Marshall’s family what Smith’s true intentions were with their relationship, and unsurprisingly he passed away less than a year after the two tied the knot. After a long legal battle regarding Howard’s estate, Smith won a significant portion of the money, but not the $800 million that she thought she was entitled to. Smith went on to become an actress, model, and spokesperson for weight loss supplements, before passing away at the age of 39 from a drug overdose. Apparently when you can afford as many drugs as you want it becomes a bit more difficult controlling your urges: be careful what you wish for, Anna.

#20 – Rossano Rubicondi (Ivana Trump)

Rossano-Rubicondi-Ivana-Trump
Ivana Trump is no stranger to gold digging, herself (as we’ll see a bit later), but she was also the subject of some particularly strong gold-diggery; in 2008 Ivana tied to knot with a rather handsome fellow named Rossano Rubicondi that was 24 years younger than her: unfortunately for her it was all for show. Rubicondi had come up with a brilliant plan to launch his career and sleep with a bunch of women: all he had to do was marry a millionaire and pop up on a bunch of shows: and that’s exactly what he did.

Right after Trump and Rossano tied the knot he was off to the races, appearing on an Italian reality program and getting the recognition he so desperately craved; Ivana was none too happy to find out that she had been used, especially after spending three million dollars on a faux wedding. Ivana may have been temporarily down, but she was definitely not out (not by a long shot), and after a few short years she was back on the prowl and looking for a guy that wouldn’t call it quits so easily.

#19 – Tori Spelling (Dean McDermott)

Dean-McDermott
Dean McDermott is a Canadian actor whose best role was convincing actress Tori Spelling to marry him: before her he had nothing going for him and now he doesn’t have to do much of anything. It’s easy to see why Tori might be interested in a guy like Dean, I mean after all he is a good looking bloke, but McDermott has a terrible track record of staying faithful or treating his partners very well; earlier in his career he cheated on his first wife, and the dude acted like a total jerk afterwards by abandoning his adopted daughter.

Tori seems interested in one thing: getting that sweet McDermott loving at home, and Dean seems interested in cashing in every time. McDermott decided to make a long term play and start having kids with Tori, and the couple popped out four children over the next few years; Dean celebrated being a father the only way he knew how: cheating on Tori and getting completely wasted. When his marriage started falling apart (which no one could have seen coming), Mcdermott checked in to rehab for alcoholism and suicidal thoughts, but perhaps it’s Tori that should be reconsidering her ability to making good decisions… because she hasn’t divorced him yet.

#18 – Courtney Stodden (Doug Hutchinson)

A lot of 16 year olds dream of marrying their high school sweetheart, but Courtney Stodden took a slightly different approach to that dream, and it probably should have been declared illegal in court: Stodden’s family happily signed off on their 16 year old’s marriage to a 51 year old millionaire, named Doug Hutchinson, knowing full well that it would pad their wallets when the two got hitched.

Courtney and Doug seemed like an odd pair right from the beginning, since Hutchinson was old enough to be her grandfather. Stodden rode the coattails of wealth to her 15 minutes of fame and began appearing on reality shows in an attempt to stay relevant in the public eye; the two split as a married couple, but Hutchinson is currently acting as Stodden’s agent, which hints at a pleasant breakup with positive (probably “beneficial”) ties. Legally we think the two should be 500 yards apart at all times, but I guess when you have enough money you can find your future wife at the local public high school.

#17 – V. Stiviano (Donald Sterling)

V-Stiviano
If you believe that V. Stiviano pursued Donald Sterling because of love, then I can’t wait to introduce you to a friend of mine who is a Nigerian Prince: he can’t wait to make you incredibly wealthy. I mean come on, Sterling is a rich guy who suddenly finds himself at the wrong end of a public persecution, and the end result is that he loses billions of dollars worth of value: do you think that’s a coincidence? Sterling was the longest tenured owner in the entire NBA (33 seasons) and because of his interactions with Ms. Stiviano it all went downhill.

Sterling was accused of being a racist and for paying for sex, which led to a lifelong NBA ban, and the forced sale of the team he owned; despite a terribly involved court battle Sterling was denied access to his team and Stiviano walked out with one heck of a check from anonymous sources. V. certainly got her fifteen minutes of fan when she appeared on nearly every talk show in the Country during the scandal, and she didn’t mind stripping every bit karat she could out of Donald’s previously golden reputation!

#16 – Kevin Federline (Britney Spears)

When you’re a backup dancer trying to make a name for yourself the easiest way is to start sleeping with the star you’re dancing behind (I mean let’s be honest, you already have a great view); that’s exactly what Kevin Federline did when he hooked up with Britney Spears, despite already having a child and another kid on the way with his girlfriend at the time, Shar Jackson. Shar didn’t have near as much money as Spears did, so we guess the choice was fairly easy for him to make when he decided how best to support little Kevin Jr. Federline used his newfound fame from the relationship to start a rap career, and crossed the line of bad taste by releasing the truly God awful song, “Popozao.”

Federline and Britney unfortunately had two children together (now we know what “Oops I Did it Again” is really about), and unsurprisingly they divorced pretty quickly after the two tots were born; Federline, of all people, got full custody of the children, and receives nearly a quarter million dollars in child support each year. Even if Federline never got the successful career that he so clearly wanted, he’s set for life now thanks to Spears.

#15 – Raffaello Follieri (Anne Hathway)

Raffaello-Follieri
Many gold diggers aren’t exposed until after it’s far too late, but Anne Hathaway got to thank her lucky stars when she dodged perhaps the biggest bullet of her entire career: a marriage to Raffaello Follieri. Before Hathaway could officially get hitched with her boyfriend (to which she had recently gotten engaged) it was revealed that he was actually a felonious embezzler responsible for more than fifty million dollars in misappropriated funds; if Follieri had gotten access to Hathway’s bank account then she would have quickly (to her dismay) found it nearly immediately empty.

Hathaway’s bride to be had presented himself as a real estate developer, but the only real estate he is looking at now is in the inside of federal prison; the subjects of his crime spree (billionaire Ronald Burke, and none other than the Catholic Church) quickly made sure that his assets were seized and liquidated, but upon his release in 2012 he was immediately deported to Italy before he could face further recourse. If Anne Hathaway wasn’t religious before 2008 then she most likely is now: that woman definitely has a guardian angel, but then again it may just be the FBI.

#14 – Rachel Hunter (Rod Stewart)

When you sign a prenuptial agreement you’re supposed to be safe if things go sour, and the idea is that you won’t have to give up much, if any, of the fortune you built; Both Steven Spielberg and Rod Stewart thought that the courts would be on their side; unfortunately, as we mentioned before, when it comes to divorce settlements things are not always so black and white, and, as you guessed it, Stewart was wrong as well which left Rachel Hunter with a big chunk of his wealth!

Stewart kind of saw the outcome of his case coming when he initially married Hunter, as she was just 21 years old while he was 45, and how can a judge to say no to those cute doe eyes? After having two children together during their marriage, Stewart figured he was safe from grabby hands until the lawyers came knocking with a purpose; Stewart lost over $65 million in the divorce, which would have been a lot more if not for the pre-nup he had constructed earlier. Stewart is 70 years old now and Hunter is enjoying the single life: let’s just hope that she at least visits the old man in his retirement home without rubbing it in!

#13 – Claus von Bulow (Sunny Crawford)

Claus-von-Bulow
Gold diggers will stoop to immeasurably low places in order to get their hands on a big fortune, but Claus von Burlow is the only one on this list crazy enough to kill his wife for it; Sunny Crawford was worth an estimated 75 million dollars at the time of her death, and the questionable state she was found in led to the arrest and imprisonment of her husband. Bulow faced first degree murder charges but he was determined to beat the case and walk out with more cash than he could ever dream of.

After five years in the slammer, complete excommunication from his entire family, two federal appeals, and list of court litigations that could keep an entire legal team busy for the next year, he was finally acquitted: the only thing it required was that he give up all rights of ownership to Crawford’s fortune. Drats! And he would have gotten away with it too if it wasn’t for those meddling kids!

#12 – Heather Mills (Paul McCartney)

1998 became a tragic year for Paul McCartney when his wife of over 30 years, Linda McCartney, tragically passed away; it was pretty clear that Linda was not in the relationship it for the money, but rather she was motivated by her genuine love of Paul which made her universally liked by fans. A couple of years after Linda’s death meant that Paul was back on the market, and it wasn’t long after he made it known that Heather Mills entered the fray: she was a model in the day that ran a modestly successful agency, but at night she was a grade A gold digger; the two were only married for six years when Mills called it quits.

Six years is a mighty short time for a marriage compared to Paul’s previous track record, which raised some serious red flags about her true intentions: this became even more obvious when Mills declared that she wanted a quarter billion in the divorce settlement, and was furious that she just got $50 million! Apparently you can put a price tag on being married to a music icon.

#11 – Alfonso Diez (Cayetana Fitz-James Stuart)

Alfonso-Diez
They say that love is blind, and in the case of Cayetana Fitz-James Stuart, the 18th Duchess of Alba, she better hope that it isn’t just a figure of speech; she got hitched to Alfonso Diaz in 2011, which wouldn’t be all that unusual if she wasn’t 85 years old, the heir to a massive fortune, and the recipient of several botched plastic surgeries that left her disfigured. Alfonso claims that his affections for the eccentric Stuart are completely genuine, and have nothing to do with her estimated 4.7 billion dollar net worth, which I might think was true if not for the fact that he quit his job and now lives like an aristocrat.

In all fairness the Duchess did sign over the majority of her wealth to her family, and Alfonso did give up the rights to Stuart’s estate, but I’d be willing to be a nonexistent fortune that opinions might changed when the Duchess of Alba kicks the bucket; if Diaz isn’t a gold digger than he has something more valuable than money itself: he has a heart made of solid 24 karat gold!

#10 – Ivana Trump (Donald Trump)

Quick, what was Ivana Trump doing before she met Donald Trump? If you don’t know then you probably aren’t alone, but she claimed to be a skier on the Czechoslovakian national team until the country found out that she was actually never a member at all.

Ivana had a previous marriage, but it was discovered to be under false pretenses so that she could get a passport and bail from communist countries: it was after that (in the late 1970s) that Ivana moved to New York in order to promote the Olympics. After Ivana met Donald in 1877 the two were married and had three children, which was pretty much the best thing she could possible ask for in terms of cementing her fortune.

The Trump marriage ended up being more prosperous for Ivana than the divorce was, because she had a large stake in Trump’s enterprise as well as in his real estate and other controlling interests; when the two split Donald was worth nearly $2 billion, but Ivana only got around $25 million in the divorce settlement (tough luck!). It looks like Ivana made the wrong choice in trying to go head to head with the most famous hairpiece in the United States, and she learned the hard way that you should never get into a legal battle with the dude who has the best lawyers in the Country.

#9 – Helg Sgarbi (Suzanne Klatten & More)


Helg Sgarbi had a scheme more complex than the pronunciation of his name, and he knew that if it was executed perfectly that it would make him wealthy for the rest of his days: seduce rich women and then blackmail the hell out of them. Helg’s plan to squeeze money out of vulnerable ladies didn’t just come out of left field, since originally he was a Swiss investment banker: and nothing says reputable and trustworthy than a guy who manages incredibly lucrative Swiss bank accounts, am I right?

Sgarbi extorted millions from his victims, which included the billionaire BMW heiress, Suzanne Klatten, and three other wealthy victims: he threatened to release explicit videos showcasing their sexual encounters, and that was all the ladies had to hear (that must have been some pretty kinky stuff). Of course the police eventually got a hold of Helg and soon after he found himself behind bars, but six years hardly seems severe enough for someone who made as much as Sgarbi did (maybe he cut himself a pretty bargain).

#8 – Crystal Harris (Hugh Hefner)

Crystal Harris is 28 years old (a little old for a Playboy Bunny), and is 60 years younger than her current husband, Hugh Hefner. Hefner has made a career out of young women, and marrying them has been part of his forte for years, which has garnered the envy of every other man in the world. Harris and Hefner were married on December 31, 2012, but they were supposed to get married on an earlier date.

Harris was engaged to Hefner for nearly six months, but just before the wedding she bailed from the Playboy Mansion and took a half a million dollar deal to star in her own reality show. After Harris realized that this wasn’t the best idea she quickly ran back to the mansion and begged Hefner for his forgiveness; Hefner relented that we all make mistakes, took her back, and the two were finally married. Don’t expect Harris to leave with a fortune to her name, because Hefner’s lawyers have made absolutely sure that a divorce will net her absolutely nothing: she’ll just have to ride that gravy train while it lasts.

#7 – Tracey Edmonds (Babyface, Eddie Murphy, & Deion Sanders)

Tracey-Edmonds
Some gold diggers are pretty good at what they do, but then there are some that just take things to the next level: Tracey Edmonds has mastered the game so well you almost have to respect her dedication to the craft of exploiting rich celebrities…almost. Over the course of her short career she has bagged and tagged three different big names: Deion Sanders , Eddie Murphy, and Babyface; if the last name on that list didn’t cement her gold digging status to you then I don’t know what will.

Edmonds has made so much money from her kiss and dip strategy that she actually managed to convert it into a massively lucrative career: she began financing feature length films and now she’s a recognizable name in the industry. Edmonds is such a master of disguise that people don’t even see her as a gold digger anymore, just as a wealthy producer that just so happens to date even more wealthy celebs. Edmonds is so deep in the gold digging game that she probably believes her own stories, but you can trust me when I say she only loves one person, and that’s Mr. Benjamin Franklin.

#6 – Vanessa Bryant (Kobe Bryant)

When Kobe Bryant was playing his third year in the NBA he met a backup dancer named Vanessa, and the two hit it off almost immediately; the only problem with Kobe and Vanessa’s relationship was that she was just 17 years old at the time they met, and Kobe was 20 (that’s a pretty big no-no in most states). Despite the obvious taboo, the two love birds surprised everyone and proceeded to get engaged a few months after meeting; Kobe and Vanessa were married without the same kind of iron clad pre-nup agreement that we saw from Hugh Hefner, and the result is that Kobe paid the price: literally!

We all remember Kobe’s infamous hotel scandal in Colorado in 2003; Kobe was charged with sexual assault but all the charges were dropped. Despite his legal innocence, many people still thought that something happened with Kobe, which is why he had to cough up a few million dollars to buy Vanessa a huge diamond ring for her forgiveness; the two are still together, but Vanessa could have made off like a bandit had she left the NBA star back then (I guess there is more money in the long con).

#5 – Evelyn Lozada (Chad Johnson)

Evelyn-Lozada
Sometimes the best thing you can do when the stakes get too high in a hand of poker is to fold, and that same rule applies to gold digging as well; when Evelyn Lozada married Chad Johnson, an NFL star that was supposed to be worth millions, she quickly realized the mistake she made and got the heck out of there. Lozada’s marriage to Chad lasted only a few weeks and the reason was simple enough: Chad’s money was draining fast with his ridiculous spending habits and he simply wasn’t all he was cracked up to be.

Chad was furious when he saw Evelyn for what she really was, and he took to every media platform he could to speak out about her manipulative, malicious, and downright predatory practices; he didn’t want anyone else to fall victim to her greed. Lozada maintained that her marriage to Chad was completely genuine, and that it was his dishonesty with the state of his financial affairs that scared her off, but she has never gotten another shot at the bank account of another athlete, so we won’t really know until then.

#4 – Kimora Lee Simmons (Russell Simmons)

Kimora Lee was 5’10” by the time she was 10 years old and would eventually reach a staggering 6’0.” Due to both her height and her beauty, Kimora landed several modeling jobs that quickly caught the eye of Russell Simmons; Simmons is a big name in the hip-hop industry, as he is the founder of both Def Jam records and Phat Farm clothing: business ventures which netted him a total net worth of $340 million.

Lee and Russell got married in 1998 and actually stayed together for a pretty long time by Hollywood standards; they divorced in 2008, but their initial separation started as early as 2006. Shortly after their separation, Kimora began a relationship with Djimon Hounsou; after the divorce was finalized, Russell Simmons was ordered to pay Kimora $40,000 each month in child support, and has to buy her a new car every three years (who knew that was a court enforceable thing !?!). Kimora went on to do a little more gold digging after she was done with Simmons, as she is now married to a banker from Goldman Sachs: This girl knows what she’s doing and there is certainly no shame in her gold digging game.

#3 – Elin Nordegren (Tiger Woods)

Elin-Nordegren-Tiger-Woods
Everyone knows Ellin Nordegren without realizing that they actually know her: she is the vixen behind the Tiger Wood scandal; Ellin walked away with a smooth 100 million dollars at the age of 33, but she wasn’t just satisfied there. With a fortune behind her Nordegren targeted the son of a widely successful billionaire, and another professional athlete, and finally with a billionaire coal investor that was more than 20 years older than her. What do you think, does Ellin happen to have a completely coincidental taste in wealthy men, or do you think it’s true love?

It takes some serious nerve to bring home a billionaire, let alone a handful of them, but Ellin certainly didn’t show up unprepared for this task: she comes from a family of politicians, and if there is anyone out there who can talk their into the pants of the top 1% it’s them. Nordegren now has more money than any of us could ever hope to have, and that isn’t all that bad for someone who started out as a nanny, eh?

#2 – Arlene Silver (Dick Van Dyke)

Arlene-Silver
Part of being a gold digger is knowing when to take advantage of an opportunity, and Arlene Silver didn’t hesitate when that opportunity presented itself; during her work as a makeup artist on set she quickly wrapped Dick Van Dyke around her finger. Arlene’s relationship wouldn’t be unusual if her partner wasn’t over twice her age! Silver just turned 42, and her husband is 87, so I’ll let you do the math about whether or not Arlene is truly the romantic she makes herself out to be.

Dick van Dyke is certainly no billionaire, but you have to give Silver credit for picking the right target: Dyke’s 30 million dollar net worth is nothing to balk at and he probably won’t be around much longer to spend it. When it comes to deciding who the greatest gold digger is of all time it’s important to remember that it’s not always about the price tag: it’s also about taking the path of least resistance, and I can’t image ol’ Dick Van Dyke is getting all that frisky at his age.

#1 – David Furnish (Elton John)

David-Furnish
David Furnish was just a regular old guy in advertising, but I doubt he would have still managed to marry Elton John if he advertised himself as what he truly was: a man trying to cash in on the fame and fortune of his incredibly wealthy and talented partner! Furnish hasn’t worked since he and Elton (one of the richest gay people in the world) became an item, and the only thing he’s done since then was a documentary about the life of his own husband: you know you’ve landed a pretty solid gig when you can make a ton of money by making a film about how you made a ton of money.

So why is Furnish number one n this list? It’s because he has been the subject of some rather sweeping accusations: that he might not actually be gay, and that the whole marriage might just be a ruse to get hold of Elton’s wealth; if that’s true then Furnish might just be the most hardcore and dedicated gold digger to walk the face of the earth…gee whiz! Can you feel the love tonight? Or is that just the feeling of insatiable greed? I’m starting to think they just might be the same thing after all.

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