Celebrities can spend years building a fortune, only to see it put at risk by the people they trust to manage it. Some of the biggest financial disasters involving famous names began with a manager, old friend, accountant, or investment adviser who seemed reliable at first. The warning signs were not always obvious, and in several cases, the money had been disappearing for years before anyone noticed. Here are 15 stories about celebrity fortunes that were threatened by the wrong people.
1. Billy Joel and the Manager Who Was Family
Billy Joel was selling millions of records and filling concert venues throughout the 1980s, so money shouldn’t have been a major concern. But behind the scenes, his relationship with longtime manager Frank Weber was falling apart. Weber was also his former brother-in-law, someone Joel had known and trusted well before their business relationship ended. In 1989, the singer filed a $90 million lawsuit accusing him of fraud, breach of contract, and mishandling his finances. Joel alleged that millions had been lost through investments and financial arrangements made without his approval. Weber denied wrongdoing, but the dispute left Joel fighting over money he had spent years earning.
2. Scottie Pippen and the Adviser Who Forged His Signature
Scottie Pippen earned considerable wealth during his NBA career and hired financial adviser Robert Lunn to help manage it. In 2002, Lunn arranged a $1.4 million loan in Pippen’s name, supposedly for an airplane investment, but used the money to repay another client and later forged Pippen’s signature on loan extensions. Lunn was eventually convicted of bank fraud, leaving Pippen tangled in a costly legal mess.
3. Leonard Cohen’s Retirement Money Was Almost Gone
Leonard Cohen had been making music for decades when he discovered that his retirement savings were in serious trouble. His longtime manager, Kelley Lynch, had handled his financial affairs for years, and Cohen accused her of taking millions from accounts that were supposed to support him later in life. He filed a lawsuit in 2005 and was awarded approximately $7.3 million in a default judgment the following year. Collecting the money proved difficult. Cohen returned to touring in 2008, already in his seventies, and spent several more years performing around the world.
4. Mike Tyson’s Bitter Split With Don King
Mike Tyson earned hundreds of millions during his boxing career, much of it while working with promoter Don King. Their relationship later collapsed into a legal battle, with Tyson accusing King of cheating him out of substantial sums. Tyson filed a $100 million lawsuit in 1998, and the case ended in a $14 million settlement in 2004. By then, Tyson was already bankrupt, with debts, taxes, and extravagant spending also contributing to his financial collapse.
5. Alanis Morissette and the Accountant Who Helped Himself
Alanis Morissette trusted Jonathan Todd Schwartz to handle the financial side of her career, including paying bills and keeping track of expenses. Between 2010 and 2014, he secretly withdrew approximately $4.8 million from her accounts. On the books, the missing money appeared as ordinary personal expenses, which helped the withdrawals go unnoticed. When questions eventually arose, Schwartz offered an explanation involving investments in marijuana-growing businesses, a story he later admitted was false. He pleaded guilty to federal fraud charges and received a six-year prison sentence in 2017. Morissette wasn’t his only victim, either.
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6. Tim Duncan and the Investment That Went Wrong
Tim Duncan kept a relatively private life, but financial adviser Charles Banks pulled him into a costly investment involving Gameday Entertainment. Duncan had already lent the company $7.5 million when Banks convinced him to sign documents that instead left him guaranteeing another $6 million loan. Banks later pleaded guilty to wire fraud and was sentenced to four years in prison. A court ordered $7.5 million in restitution, which Duncan later accepted to settle his lawsuits.
7. John Elway and the $15 Million Investment Disaster
John Elway had made a successful transition from NFL quarterback to businessman after retiring from football. But in 2010, he and business partner Mitchell Pierce found themselves trying to recover $15 million they had transferred to hedge fund manager Sean Michael Mueller. The money was supposed to be held in trust while they considered investment opportunities. Instead, Mueller’s operation was collapsing amid allegations that he had been running a Ponzi scheme. Investigators found that his company had far fewer assets than its obligations to investors. Elway and Pierce went to court seeking to recover their funds, joining a group of investors caught up in the financial mess.
8. Sting and the Accountant With Expensive Ideas
Sting had trusted accountant Keith Moore with his finances for roughly 15 years, leaving him to deal with much of the business side of an extremely successful music career. Moore used approximately £6 million of the singer’s money without authorization, putting funds into ventures that included restaurants and a plan to convert Russian military aircraft for civilian use. Some of the money also went toward Moore’s personal debts. The scheme eventually unraveled, and he was sentenced to six years in prison in 1995. Sting managed to recover nearly all the stolen funds, but the court case revealed just how much his accountant had been doing without his knowledge.
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9. Nicolas Cage and the Manager He Blamed for His Financial Troubles
Nicolas Cage’s spending habits became almost as famous as his movies during the 2000s. He purchased numerous properties and expensive collectibles, apparently confident that his movie earnings could support the lifestyle. When serious financial problems emerged, Cage accused his former business manager, Samuel Levin, of failing to protect him from financial disaster. The actor filed a $20 million lawsuit in 2009, alleging negligent advice and risky financial decisions. Levin responded that he had repeatedly warned Cage about his spending. Both lawsuits were dismissed in 2010, without a court determination that Levin caused Cage’s losses. The actor still faced substantial tax debts and began selling assets to improve his finances.
10. Dane Cook and the Brother Who Stole His Earnings
Dane Cook was one of America’s highest-profile stand-up comedians during the 2000s, performing to large audiences and earning millions from tours and entertainment deals. His half-brother, Darryl McCauley, managed his business affairs and had access to the money coming in. McCauley and his wife, Erika, eventually admitted to stealing from the comedian, with the couple ordered to pay $12 million in restitution. Darryl received a prison sentence of five to six years in 2010. The money was a major loss, but having his own brother involved made the case particularly unpleasant for Cook.
11. Kevin Bacon and Kyra Sedgwick’s Madoff Nightmare
For years, Bernie Madoff appeared to be exactly the sort of person wealthy investors wanted handling their savings. His investment business reported unusually consistent returns, and his reputation attracted clients from Hollywood as well as Wall Street. Kevin Bacon and Kyra Sedgwick were among those who trusted him. When Madoff’s massive Ponzi scheme collapsed in December 2008, the couple discovered that much of their savings had been caught up in the fraud. Bacon later said they had placed most of their money with Madoff, although he never publicly confirmed an exact loss figure. They recovered some funds through the compensation process and continued working, but the experience dramatically changed their financial circumstances.
12. Kareem Abdul-Jabbar and the Manager Who Controlled His Money
Kareem Abdul-Jabbar was still playing for the Los Angeles Lakers when he discovered that his finances were in worse shape than he had imagined. For six years, business manager Thomas Collins had enjoyed almost complete control over his money, arranging investments in hotels, restaurants, oil ventures, and even Arabian horses. Many of those investments went badly, leaving Abdul-Jabbar struggling to cover debts despite his substantial NBA earnings. In 1986, he sued Collins for $55 million, accusing him of fraud, negligence, and financial mismanagement. By the following year, reports suggested that Abdul-Jabbar could lose at least $5 million through the failed investments. Collins disputed the allegations, but the financial damage and the collapse of their relationship were already evident.
13. Dennis Rodman and the Woman Who Called Herself His Financial Adviser
Dennis Rodman earned millions during his NBA career, but some of his financial trouble came from someone he trusted to manage his money. Peggy Ann Fulford claimed impressive credentials and offered to handle his expenses and savings, but instead used access to his accounts for her own benefit. Rodman cut ties with her in 2015, and investigators later found that she had targeted several professional athletes. In 2018, Fulford was sentenced to ten years in prison and ordered to pay nearly $5.8 million in restitution.
14. Rihanna and the Accountants Who Cost Her Millions
Rihanna hired accounting firm Berdon LLP as a teenager, but later claimed her finances were being badly mishandled despite her growing success. In a 2012 lawsuit, she accused the firm of charging excessive commissions, failing to warn her about mounting expenses, and advising her to buy a $7 million Beverly Hills mansion that she later sold at a loss. The accountants denied wrongdoing, and the case ended in a confidential settlement in 2014.
15. Elton John and the Manager He Trusted for Decades
Elton John worked with manager John Reid for decades before their relationship ended in a financial dispute. After they split in 1998, Elton questioned millions in overseas touring expenses that he believed should have been covered by his management company. Reid later settled with him for about £3.4 million, but Elton’s separate negligence case against former advisers failed in 2001, leaving him with substantial legal costs.
In the mood for more?
Check out 14 Celebrities Who Worked as Waiters Before Their Break, or take a look at 14 Infamous Scams That Millions of People Fell For. If you want to see more stories about lost fortunes, you can check out 12 of the Most Atrocious Financial Decisions Made In History.
