History’s 50 Most Notorious Gold Diggers

Some people seek romance, while others pursue wealth. Throughout history, numerous high-profile relationships have been driven more by financial incentives than by love. This article profiles well-known figures who have been accused, questioned, or simply perceived as having benefited financially—through settlements, marriages, or strategic relationships—often generating controversy and public fascination.

Oksana Grigorieva

Oksana Grigorieva, a Russian-born singer, songwriter and pianist, became widely known for her relationship with actor Mel Gibson. Their breakup produced a high-profile legal dispute that concluded with Grigorieva receiving $750,000 and joint custody of their child. She later sued her attorneys, alleging mishandling of her settlement. Grigorieva trained at conservatories in Moscow and Kazan and has a career in music beyond the headlines.

Elin Nordegren

Former nanny Elin Nordegren was thrust into global attention after her marriage to golfer Tiger Woods ended amid scandal. Her divorce reportedly secured a settlement around $100 million, providing her with financial independence and freedom to pursue relationships and interests outside of her former role.

Helg Sgarbi

Helg Sgarbi is known for targeting wealthy individuals. In one notorious case, he blackmailed BMW heiress Susanne Klatten using secret recordings and extracted millions before being arrested. Both he and an accomplice who recorded the tapes were later convicted and imprisoned.

Gabriel Aubry

Canadian model Gabriel Aubry became a tabloid fixture after his relationship with actress Halle Berry ended. In custody and support disputes, he sought substantial child support payments. The legal battles yielded monthly payments and significant legal fees, making the dispute more notable than his modeling work.

Amy Irving

Amy Irving’s divorce from director Steven Spielberg drew attention when a judge rejected their prenup and awarded her a substantial settlement reportedly around $100 million. Irving, an actress with an Academy Award nomination to her name, saw her personal life become a prominent Hollywood story.

David Furnish

Before his marriage to Elton John, David Furnish worked in advertising and film. The partnership with John brought public scrutiny, with critics questioning Furnish’s motives. Regardless, the couple’s collaboration has led to shared projects and a comfortable lifestyle for Furnish.

Amber Heard

Amber Heard’s relationship with Johnny Depp ended amid highly publicized allegations of abuse from both parties. Heard received an approximately $7 million settlement that she later stated she donated to charity. The legal and media battles around the case had careers and reputations on both sides affected in different ways.

Antony Armstrong-Jones

Antony Armstrong-Jones, known as Lord Snowdon, married Princess Margaret in 1960. Their union brought him into royal circles and public life; even after their divorce in 1978, he retained his title. His marriage and subsequent lifestyle remain part of his public legacy.

Raffaello Follieri

Raffaello Follieri gained notoriety for a fraud case that engulfed his relationship with actress Anne Hathaway. Prosecuted for conspiracy and money laundering after defrauding investors with false Vatican connections, Follieri served prison time. Hathaway was not charged but experienced intense media scrutiny during the investigation.

Heather Mills

Heather Mills received a significant settlement following her divorce from Paul McCartney, a case that stirred widespread media commentary. Previously known for her activism and modeling, Mills’s post-divorce life and public statements continued to attract attention and debate.

Dean McDermott

Actor Dean McDermott left his first marriage and later wed actress Tori Spelling. Their often-publicized relationship was featured on reality television and fueled rumors about motivations tied to fame and family wealth. Infidelities and reconciliations became part of their very public narrative.

Courtney Love

Courtney Love married Kurt Cobain in 1992 and later became a central figure in disputes over Nirvana’s estate after his death. Her role in managing the band’s legacy and the public controversies that followed have kept her name associated with questions about influence and gain.

Guy Ritchie

Director Guy Ritchie’s marriage to Madonna included a lavish lifestyle and significant public attention. Their divorce in 2008 reportedly involved a settlement near $80 million. The split followed years of high-profile living and mutual public commentary.

Rachel Hunter

Model Rachel Hunter married Rod Stewart at a young age and later divorced, reportedly receiving a substantial settlement despite a prenuptial agreement. Her marriage and subsequent financial outcome drew attention to the disparities in age and wealth between partners.

Kevin Federline

Kevin Federline, initially known as a backup dancer, rose to fame through his relationship with Britney Spears. Their marriage and divorce resulted in monthly child support payments and considerable media attention, which shaped much of Federline’s public profile.

Rick Salomon

Rick Salomon’s brief marriages to Pamela Anderson and his involvement in widely publicized scandals kept him in the spotlight. One divorce reportedly resulted in a seven-figure payout. Salomon’s public life has been marked by controversy and attention-grabbing incidents.

Tameka Raymond

Tameka Raymond, a well-regarded stylist, married singer Usher and later became involved in contentious custody and financial disputes. While she built a career working with high-profile artists, her marriage and its aftermath attracted significant legal and media attention.

Alma Mahler Werfel

Alma Mahler Werfel was a socialite who married several prominent men—including composer Gustav Mahler and architect Walter Gropius—and has been much discussed by biographers. Her relationships with influential cultural figures and the complexities of her personal life have made her a controversial historical figure.

Kris Humphries

Kris Humphries gained international attention after his short-lived marriage to Kim Kardashian, which lasted about 72 days. Although he did not secure a large divorce settlement, the publicity surrounding the marriage and its aftermath boosted his public profile and led to further opportunities.

Casper Smart

Choreographer Casper Smart rose to greater visibility through his relationship with Jennifer Lopez. She supported him financially and professionally, elevating his career from dancer to featured choreographer during their time together.

Marion Davies

Actress Marion Davies enjoyed a long association with newspaper magnate William Randolph Hearst, who used his influence and resources to advance her film career. While opinions vary about her talent, Hearst’s backing allowed Davies to maintain a prominent position in Hollywood for decades.

Andrew Robinson Stoney

Andrew Robinson Stoney’s marriage to heiress Mary Eleanor Bowes in the 18th century became notorious for the deception and abuse she endured. He reportedly manipulated and controlled her, squandering her wealth until courts intervened and granted her a rare divorce for the era.

Kimora Lee Simmons

At 23, Kimora Lee Simmons married music executive Russell Simmons. After their divorce, she reportedly received monthly payments and other benefits that helped her build and expand her own fashion business, establishing her as an entrepreneur in her own right.

Sarah Ferguson

Sarah Ferguson, the Duchess of York, married Prince Andrew in 1986. Although her divorce did not yield an enormous settlement, her royal connection opened doors to business and public opportunities. A later scandal involving allegations of offering access harmed her reputation and confirmed lingering suspicions about exploiting royal ties.

Anna Nicole Smith

Anna Nicole Smith married elderly oil magnate J. Howard Marshall and later litigated for a portion of his estate after his death. The lengthy legal battles over his fortune drew international attention and continued long after both their deaths, highlighting complex issues around wills and inheritance.

Ivana Trump

Ivana Trump’s divorce from Donald Trump resulted in a settlement that included cash, property, and ongoing financial arrangements. She parlayed her profile and business acumen into continued entrepreneurial efforts after the marriage ended.

Peggy Hopkins Joyce

Peggy Hopkins Joyce became notorious in the early 20th century for marrying wealthy men and living an extravagant lifestyle. Famous for lavish spending and numerous high-profile relationships, she embodied a public image of glamour, excess, and scandal.

Diane Richie

Diane Richie, formerly married to Lionel Richie, received a significant settlement at the time of their divorce. Reported maintenance amounts designated for personal care became a focal point of media commentary, reflecting public interest in the lifestyles of celebrity couples.

Lamar McDow

Lamar “Hot Sauce” McDow became linked to lottery winner Marie Holmes, who reportedly spent millions on his legal bail and related expenses. The financial support she provided drew heavy criticism and underscored the risks that can accompany sudden wealth and personal relationships.

David Gest

David Gest’s marriage and subsequent divorce from Liza Minnelli produced a contentious legal battle. He pursued claims against her and attempted to challenge prenups and other agreements, though courts did not grant the relief he sought. The dispute damaged both parties’ finances and reputations to varying degrees.

Orianne Cevey

Translator Orianne Cevey married musician Phil Collins and later received a reported settlement in the millions when they divorced. The couple reunited for a time thereafter, but their relationship ultimately faced further complications when Cevey married someone else while living with Collins, resulting in a public falling-out.

Eric Johnson

Former NFL player Eric Johnson married singer and businesswoman Jessica Simpson. While Johnson stepped back from his own professional pursuits to focus on family, Simpson’s continuing success as a brand owner made her the primary earner in the household, enabling a comfortable family lifestyle.

Holly Madison

Holly Madison rose from difficult circumstances to become Hugh Hefner’s most public girlfriend and a central figure at the Playboy Mansion. While she gained fame and financial security, she later spoke publicly about the limitations and controls she experienced during that period.

Arlene Silver

Makeup artist Arlene Silver married actor Dick Van Dyke later in his life. Their relationship received media coverage, and Van Dyke publicly described Silver as a source of support. Observers noted that marriage to a well-established star could offer financial stability and public recognition.

Stiviano

V. Stiviano received luxury gifts from Los Angeles Clippers owner Donald Sterling and later became central to a scandal that included secretly recorded remarks by Sterling. Legal action ultimately forced Stiviano to return many of the gifts, and the episode led to Sterling’s removal from team ownership.

Matt Rutler

Production assistant Matt Rutler met Christina Aguilera on the set of Burlesque and has since shared family life with the singer. Rutler has maintained a relatively private profile while enjoying the benefits of Aguilera’s success, including a family home and the stability that comes with it.

Rene Elizondo

Dancer Rene Elizondo was married to Janet Jackson and later sued for compensation related to his claimed contributions to her work. Their settlement reportedly resolved for a multi-million dollar figure, reflecting the value and complexity of creative partnerships in entertainment.

Meghan Markle

Meghan Markle transitioned from a television actress to an internationally known public figure after marrying Prince Harry. Their decision to step back from senior royal duties and subsequent commercial deals transformed their income streams and global profile.

Melinda Gates

Melinda Gates, who married Bill Gates in 1994, pursued philanthropic work alongside her husband before their divorce in 2021. Public filings and reports indicated she received significant assets as part of their separation, and she has since continued to lead philanthropic initiatives.

Yoko Ono

Yoko Ono’s relationship with John Lennon sparked intense public debate in the 1960s, with some fans blaming her for tensions within the Beatles. After Lennon’s death, Ono continued to manage his legacy and artistic estate, overseeing exhibitions, releases, and projects that preserved and expanded public access to Lennon’s work.

These stories illustrate the varied and often complicated intersections of love, power, and money. In many cases, public perception simplifies complex relationships into narratives of gain or exploitation, but the truth is usually more nuanced—shaped by legal rulings, personal choices, public scrutiny, and the lasting consequences each person faces.