History’s 50 Most Shameless Gold Diggers
Some people chase love. Others chase bank accounts. Over the years, countless marriages have been built less on romance and more on financial gain. These gold diggers made history for securing the ultimate paycheck through outrageous divorce settlements, shady prenups, and suspiciously timed breakups.
Oksana Grigorieva
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Before her relationship with Mel Gibson, Oksana Grigorieva allegedly sought a wealthy partner. She left with $750,000 and joint custody while suing her lawyers for mishandling her settlement. The Russian singer-songwriter is also a pianist who began studying music in Moscow and then completed formal conservatoire training in Kazan.
Elin Nordegren
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Elin Nordegren went from nanny to millionaire overnight when she secured $100 million following her divorce from Tiger Woods. After his cheating scandal unraveled their marriage, she dated billionaire Chris Cline and NFL player Jordan Cameron. Her wealthy connections and financial cushion allow her to live a life that’s leagues above babysitting.
Helg Sgarbi
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Helg Sgarbi targeted rich women, including BMW heiress Susanne Klatten. He blackmailed her with secretly recorded tapes and got millions before being caught. He went to prison, and his accomplice, who filmed everything, was also sentenced.
Gabriel Aubry
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Canadian model Gabriel Aubry made headlines more for court dates than catwalks. After splitting from Halle Berry, he demanded $20,000 per month in child support. He doesn’t even have full custody of their daughter. Still, he scored $16,000 monthly and over $400,000 in legal fees and retroactive payments combined.
Amy Irving
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A napkin scribble turned into a jackpot for Amy Irving when her $100 million divorce settlement from Steven Spielberg shocked Hollywood. Their prenup was thrown out by a judge. Her acting career fizzled, but she did earn an Academy Award nomination for Best Supporting Actress in “Yentl.”
David Furnish
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Despite lingering accusations about his motives, David Furnish was the one who co-directed the acclaimed 1997 documentary “Elton John: Tantrums & Tiaras.” Before marrying Elton John, he was just an ad exec with modest success. Their relationship catapulted him into a lavish lifestyle with no financial worries.
Amber Heard
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Hollywood hadn’t really noticed Amber Heard before she started dating Johnny Depp. They married in 2015 and divorced a year later. After claiming abuse and leaking audio, she walked away with $7 million. Depp lost key roles, while Amber kept hers—especially in the “Aquaman” franchise despite all the controversy.
Antony Armstrong-Jones
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After marrying Princess Margaret in 1960, Antony Armstrong-Jones lived like royalty—literally. Despite constant affairs and questionable behavior, he retained his Earl title after their 1978 divorce. He even had children outside the marriage.
Raffaello Follieri
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Anne Hathaway’s relationship with Raffaello Follieri ended in scandal when he was arrested for fraud, conspiracy, and money laundering after stealing millions from investors by pretending to have Vatican connections. Hathaway wasn’t involved in his crimes, but her diaries were confiscated during the investigation because she was close to him. She faced public embarrassment but was never charged or accused of wrongdoing. Follieri served part of his prison sentence before being deported.
Heather Mills
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Marrying Paul McCartney earned Heather Mills a divorce payout close to $50 million. That amounted to nearly $25,000 per day of marriage. Her claims of abuse fell apart, and even her publicist quit after discovering her dishonesty. Years before the headlines, she was a model and activist, receiving an award for her landmine awareness charity work.
Dean McDermott
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Dean McDermott left his first wife the night he met actress Tori Spelling. The two married in 2006 and became well-known for their reality TV shows. Some critics claimed McDermott was motivated by Spelling’s family wealth. Later, McDermott admitted to cheating on Spelling, and the couple turned their attempts to repair their marriage into a reality show.
Courtney Love
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Courtney Love married Kurt Cobain in 1992 and was soon suspected of exploiting his fame. After his death, she gained control over much of Nirvana’s estate. Allegations about her influence on his drug use and mental health still cast a shadow over everything.
Guy Ritchie
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While married to Madonna, Guy Ritchie lived extravagantly and used her money for jets, mansions, and even a pub. When they divorced in 2008, he got an $80 million settlement. The split came after he mocked the marriage publicly. Madonna simply signed the check and moved on.
Rachel Hunter
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Model Rachel Hunter was only 21 when she married 45-year-old Rod Stewart. Despite a prenup, she still got $65 million when they divorced after 16 years. She had dated musician Kip Winger before Stewart but upgraded to serious cash. After the split, she moved on to professional hockey players.
Kevin Federline
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As Britney Spears’ backup dancer, Kevin Federline left his pregnant partner to be with the pop icon. Two kids and a divorce later, he was awarded $20,000 a month in child support. He tried rapping and reality shows, but his only real income came from being Mr. Britney Spears.
Rick Salomon
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Rick Salomon briefly married Pamela Anderson—twice. The first union ended in an annulment after five months. The second got him $1 million in the divorce. He was known for his infamous tape with Paris Hilton and profited from controversy by smartly claiming residency in tax-free Nevada.
Tameka Raymond
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Stylists usually don’t land millionaires, but Tameka Raymond married Usher and tried to stay wealthy after their divorce. She lost custody of their kids and credibility in court. Still, before the legal drama, she had built a solid career as a celebrity stylist, working with high-profile clients like Lauryn Hill and Patti LaBelle.
Alma Mahler Werfel
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Alma Mahler married composer Gustav Mahler, architect Walter Gropius, and poet Franz Werfel—while cheating on each of them. Her memoirs were full of lies and complicated biographical records. She latched onto genius after genius and spun her muse role into long-term survival. Historians now refer to her as “The Alma Problem.”
Kris Humphries
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After marrying Kim Kardashian, Kris Humphries went from an average NBA player to a tabloid fixture. Their marriage lasted 72 days, followed by a televised special that profited heavily. While he didn’t get a payout, the exposure gave his career a boost. At his peak, he signed an $8 million contract with the Brooklyn Nets, his most lucrative NBA deal.
Casper Smart
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Jennifer Lopez funded Casper Smart’s lifestyle by paying him $10,000 a week and promoting him from dancer to choreographer. He stuck around from 2011 to 2016 and reaped the benefits until she discovered his cheating.
Marion Davies
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Actress Marion Davies gained stardom through her relationship with newspaper mogul William Randolph Hearst. He funded her films, promoted her in the press, and shaped her career. Despite limited talent, she starred in over 40 movies. Hearst never divorced his wife, but Davies still lived like a queen for decades.
Andrew Robinson Stoney
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To marry heiress Mary Eleanor Bowes, Andrew Stoney faked a duel injury and proposed from his “deathbed.” After marrying her, he locked her away and burned through her fortune. His cruelty was so extreme that even 18th-century courts granted her a divorce, which was rare for women at the time.
Kimora Lee Simmons
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At just 23, Kimora Lee Simmons married hip-hop mogul Russell Simmons, then worth over $300 million. After their 2008 divorce, she received $40,000 a month, a luxury car every three years, and leveraged her control of Phat Farm into her own fashion empire.
Sarah Ferguson
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Sarah Ferguson married Prince Andrew in 1986 and divorced just five years later. Though she didn’t take a huge financial settlement, she used the royal connection for business deals. In 2010, she was caught offering access to Andrew in exchange for money. That scandal confirmed many long-standing suspicions.
Anna Nicole Smith
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Anna Nicole Smith married 89-year-old oil tycoon J. Howard Marshall, after meeting him as a dancer. They were married for just one year before he died. Smith went to court to claim part of his fortune, even though he hadn’t included her in his will. The legal fight continued for years, with her partner and their daughter also seeking a share of the estate.
Ivana Trump
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Ivana Trump secured $20 million, a mansion, and hefty alimony after divorcing Donald Trump. Their marriage ended due to his affair, but her business moves after the divorce were just as sharp. She married a man previously only for citizenship and milked every advantage of being a former Trump.
Peggy Hopkins Joyce
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Peggy Hopkins Joyce became famous for marrying rich men and spending their fortunes. She had six husbands, all wealthy, and countless affairs. She’s even known for blowing $1 million in a single week, which inspired lyrics by Cole Porter. Interestingly, she also owned one of the world’s largest emeralds—the 125-carat “Spanish Inquisition” emerald—set in a platinum necklace.
Diane Richie
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Diane Richie married Lionel Richie and lived lavishly until their 2004 divorce. She received $20 million and monthly maintenance that included $50,000 for beauty, $15,000 for clothes, and $20,000 for surgeries. The court approved her “necessities,” so much so that she’d never need a coupon again in her life.
Lamar McDow
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Lottery winner Marie Holmes spent over $21 million bailing out Lamar “Hot Sauce” McDow from jail repeatedly. He faced drug and weapons charges while she footed every bond. At one point, she paid $12 million after a high-speed chase. The jackpot clearly bought him more chances than sense.
David Gest
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David Gest’s divorce from Liza Minnelli was as messy as it gets. He sued for $10 million after alleging abuse and hiding an STD, claiming this invalidated their prenup. Though the court threw it out, he tried everything to get more than he deserved. He sold possessions when the money ran dry.
Orianne Cevey
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Translator Orianne Cevey married Phil Collins, divorced him for $46 million, and then got back together years later. While they were living together again, she secretly married another man without telling Collins. He kicked her out of their Miami home after the betrayal.
Eric Johnson
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Former NFL player Eric Johnson was jobless when he began dating Jessica Simpson. The couple married in 2014 and now have three children. While Johnson stepped back from his own career to focus on family, Simpson became the primary breadwinner with her billion-dollar fashion brand. Together, they live in a $10 million estate purchased by Simpson.
Holly Madison
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Hugh Hefner took Holly Madison in when she was broke and nearly homeless. As his “main girlfriend,” she lived at the Playboy Mansion from 2001 to 2008. She couldn’t earn outside income or have much freedom, but she did get fame and financial security—at least temporarily—out of the arrangement.
Arlene Silver
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Makeup artist Arlene Silver married Dick Van Dyke in 2012 when he was 86 and she was 40. They met six years earlier at the SAG Awards. He later called her his “saving light,” though critics pointed out she’d never have to worry about money again thanks to his legacy
Stiviano
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V. Stiviano was gifted luxury cars, a $1.8 million duplex, and hundreds of thousands in spending money by Los Angeles Clippers owner Donald Sterling. When recordings of Sterling’s racist comments surfaced, it was revealed she’d taped him. Sterling lost his team, and his wife sued Stiviano, ultimately forcing her to return everything.
Matt Rutler
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Production assistant Matt Rutler met Christina Aguilera on the “Burlesque” set. They’ve been together ever since. While Aguilera earns millions, Rutler remains relatively unknown. He helped raise their child and lives in a mansion she bought for $10 million. It’s safe to say he hit the jackpot backstage.
Rene Elizondo
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Dancer Rene Elizondo kept his 1991 marriage to Janet Jackson a secret for years. When they divorced in 2000, he sued her for $25 million, claiming emotional distress and creative contributions. The case settled for $10 million—far more than anything he ever earned from his own entertainment career.
Meghan Markle
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Before marrying Prince Harry, Meghan Markle was best known for her role in “Suits.” The jump from basic cable to royalty turned her into a global household name. After stepping back from royal duties, she and Harry landed major deals worth millions.
Melinda Gates
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Melinda Gates married the world’s richest man in 1994 and divorced him in 2021. While exact financial terms weren’t disclosed, stock transfers showed she received billions. Their split was so friendly it barely made a dent in Bill Gates’ public image. Following the divorce, she launched her own philanthropic venture, Pivotal Ventures.
Yoko Ono
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The moment John Lennon left Cynthia Powell, fans blamed Yoko Ono for wrecking the Beatles. After marrying him in 1969, she steered his art and politics. Even after Lennon’s death, she profited from his name through exhibitions and projects, despite having no real connection to his bandmates or their legacy.