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Rich Celebrities Who Went Broke and Declared Bankruptcy

$1.2 million is a lot of money. According to The Hamilton Project , that’s about what the typical four-year degree holder earns over the co...

$1.2 million is a lot of money. According to The Hamilton Project, that’s about what the typical four-year degree holder earns over the course of their career. 

Some majors earn more – up to $2 million or so. Others earn less – just $800,000. Other factors, including geography and career trajectory, obviously factor into these calculations as well.

$1.2 million in career earnings might be enough to support a comfortable family life through three to four decades. However, for most celebrities who’ve achieved household-name status, it’s pocket change. A-list film stars earn 20 times the lifetime earnings of the average bachelor’s degree holder – for a single film. Top athletes can easily pull down $20 million or more per year, depending how their contracts are structured. After accounting for endorsements and business ventures, their earnings can be much higher.

How much higher? Despite earning “just” $93 million in salary during his NBA career, former Chicago Bulls superstar and current Charlotte Bobcats majority owner Michael Jordan was worth some $1.14 billion in 2016, per The Richest. Following the sale of his Beats headphones line to Apple in 2014, Dr. Dre had some $700 million in the bank, per Forbes.

Dre and Jordan are sitting pretty, but not all of their larger-than-life peers can say the same. Despite raking in vast sums of money during playing, performing, and business careers, a shocking number ofcelebrities face financial ruin when work dries up or the consequences of poor past decisions finally rear their heads.

These six public figures all earned tens of millions, at minimum, during their careers. Five – Donald Trump, Mike Tyson, Michael Vick, Curt Schilling, and 50 Cent – have declared personal or business bankruptcy at least once. Nicolas Cage, the “lucky” one here, squandered a vast fortune and lost his home due to crushing tax debts. Their stories serve as cautionary tales – and, in some cases, hopefully lessons – for anyone struggling with overwhelming financial pressure, no matter how modest the sums involved.
1. Donald Trump: Prior to his surreal run for the presidency, Donald Trump was best known as a brash New York real estate developer with an outrageous hairstyle, high-profile romantic exploits, and a true gift for self-promotion. What was lesser known, though by no means secret, was that Trump-owned businesses declared bankruptcy no fewer than six times between 1991 and 2009.

Trump inherited the family business from his father, Fred Trump, a successful New York City builder and landlord. Whereas his father made his fortune building single-family homes, and later running large apartment complexes in New York’s outer boroughs, Donald went for bigger, flashier prizes: Manhattan high-rises, Atlantic City casinos, Florida resorts, and ultimately a network of branded hotels, casinos, golf courses, luxury residences, media productions, and random business ventures (such as the infamous Trump Steaks) around the world.

Many of his later ventures were low-risk licensing arrangements that found Trump charging impressive fees to attach his name to projects financed by others (Forbes describes how some of these arrangements worked). During the 2000s, Trump devoted much of his personal attention to high-profile media ventures, such as “The Apprentice,” “Celebrity Apprentice,” and the Miss Universe pageant.
What Happened: Six Trump-owned businesses filed Chapter 11 bankruptcy in the 1990s and 2000s, according to PolitiFact. Five were gaming enterprises, including the famed Trump Taj Mahal and its parent company, Trump Hotels and Casinos Resorts. Most bankruptcies occurred during or following the major real estate downturns of the early 1990s and mid- to late-2000s.

Trump’s first bankruptcy, filed in 1991, was arguably the most devastating for the man’s lifestyle. Trump funded the $1 billion Trump Taj Mahal with loads of high-interest debt, and within a year of opening, the property was more than $3 billion in the hole. Trump was personally on the hook for $900 million. The eventual settlement required Trump to sell his money-losing airline, Trump Shuttle (DBA “Trump Airlines”), and offload his personal yacht.

Subsequent Trump bankruptcies also involved eye-popping numbers – for example, Trump Hotels and Casinos Resorts was more than $1.8 billion in debt when it first filed for Chapter 11 in 2004 (and a second filing would come in 2009).

However, they didn’t affect his personal finances or lifestyle to the same extent, largely because Trump did not personally guarantee the loans that financed the struggling projects. Trump’s latter-year pursuit of low-risk licensing arrangements make it less likely that his ventures will face serious financial problems going forward – a fortuitous development for a presidential candidate.
Post-bankruptcy Activities

Following his most recent bankruptcy, Donald Trump sought the spotlight with renewed vigor. In 2011, he flirted with a presidential run, leveraging debunked theories of President Obama’s foreign birth to ingratiate himself with a disgruntled subset of conservative America. He abandoned his quest after the State of Hawaii released Obama’s long-form birth certificate, and subsequently endured a brutal roast (including from President Obama himself, as reported in the The New Yorker and elsewhere) at the 2011 White House Correspondents’ Dinner.

Trump’s humiliation in 2011 may well have hardened his political ambitions. In June 2015, he launched his first official presidential campaign with a rambling speech that scapegoated immigrants, ethnic minorities, and political elites. He spent the following 12 months in similar form, upending years of accumulated political wisdom with his bombast and dispatching a deep Republican primary field by May 2016.

Even if he doesn’t win the presidency, Trump’s run will likely reverberate through American politics for years to come. Anyway, he may have a face-saving out, per Vanity Fair: a new, as-yet-unnamed conservative media rival to Fox News. Given his unprecedented visibility and name recognition, a Trump-branded news network could even turn a profit, no matter how overrated its founder’s business skills.
Rich Celebrities Who Went Broke and Declared Bankruptcy
What We Can Learn: Politics aside, it’s heartening to see that serious financial troubles do not disqualify brash, self-described billionaires from the presidency.

More importantly, Trump’s financial history demonstrates that American bankruptcy laws function as a gaping escape hatch for businesspeople facing financial ruin. Trump successful used bankruptcy to salvage at least some of his fortune, and keep his business empire intact, when the going got tough. Aside from the 1991 bankruptcy, Trump’s successive brushes with insolvency did not adversely affect his personal wealth or lavish lifestyle. Whether his reputation survived unharmed is another question entirely.

If you’re self-employed and have yet to form a business structure that can insulate your personal assets from your business activities, what are you waiting for? It certainly worked out for Trump.
2. Mike Tyson: Widely regarded as one of the greatest boxers of the modern era, “Iron Mike” Tyson exploded onto the scene as a junior boxer in the early 1980s. He earned the WBC heavyweight champion title just four months after his 20th birthday, becoming the youngest boxer ever to reach that mark. He won an astonishing 26 out of 28 fights by knockout, an impressive feat in an increasingly safety-conscious boxing culture.

According to a comprehensive 2003 report by The New York Times, Tyson earned approximately $400 million during the first 18 years of his boxing career. But all the money in the world couldn’t help Tyson. Out of the ring, his run-ins with the law, including a sexual assault conviction that landed him in prison for three years, were frequent and disturbing. In the ring, despite his early successes, he’s perhaps best remembered for the ill-fated 1997 comeback bout known as “The Bite Fight,” in which he bit opponent Evander Holyfield’s ear hard enough to draw blood – twice. Tyson finally declared personal bankruptcy in 2003, and has devoted his time since to rehabilitating his reputation.

What Happened: Tyson raked in $30 million per fight at the peak of his career, but he bled money as readily as he earned it. In 2003, the Times called him “a cash machine to himself and others,” detailing lavish spending on “jewelry, mansions, cars, limousines, cellphones, parties, clothing, motorcycles, and Siberian tigers.” In December 2002, he bought a $173,000 gold chain on credit, adding it to the $27 million in debts listed in his 2003 bankruptcy filing.

Tyson’s largest debts included a $17.4 million in tax liabilities to U.S. and British authorities, a $9 million divorce settlement with former wife Monica Turner, several million in obligations to a gaggle of lawyers and producers, and more than $300,000 to a limousine company. His largest assets included a Farmington, Connecticut mansion, soon sold to fund the divorce settlement, and two extravagant properties in Las Vegas.

At the time of his bankruptcy filing, Tyson was pursuing a $100 million lawsuit against boxing promoter Don King, who Tyson claimed bilked him out of millions of dollars in revenue. In 2004, he settled with King for $14 million, according to the Times – trimming, but not eliminating, his debts. Tyson did eventually exit bankruptcy after forfeiting much of his trove of physical assets and setting aside a substantial share of his future earnings to pay lienholders.
Post-bankruptcy Activities: Far past his prime, Tyson continued boxing for several years after emerging from bankruptcy, most memorably in a 2006 “comeback” tour with a veteran boxer in even worse shape than he. Tyson also sought out endorsement relationships to help pay the bills. He found some success, though most major brands refused to associated with him on account of his criminal history and uncouth image. Tyson also pursued acting and music, making an extended self-cameo in the 2009 comedy hit “The Hangover” and starring in a Spike Lee-produced one-man show that hit 36 cities and culminated in an HBO special.

After a series of arrests, including for driving under the influence and fighting a reporter in Los Angeles International Airport, Tyson sought sobriety and calmed his personal life. In 2013, he released a bestselling book, “Undisputed Truth,” and he guest-sang on a Madonna track two years later.

What We Can Learn: Tyson grew up in the roughest parts of New York City back in the 1970s, when the city was on the verge of municipal bankruptcy. His father abandoned his family two years after his birth. Homelessness was a constant threat, and sometimes a reality, during his childhood. His mother passed away when he was 16, leaving him to the care of his boxing trainer and mentor. He escaped poverty only by virtue of his athletic talent and dogged work ethic.

Given the emotional scars etched by his difficult childhood, it’s understandable that Tyson would struggle with powerful demons as an adult. His story is a cautionary tale about the perils of having it all when you’re young, immature, and perhaps not fully ready to handle the demands of fame. Happily, Tyson’s post-bankruptcy years support the contention that anyone can change.
3. Michael Vick: Gifted NFL quarterback Michael Vick is unfortunately best known for the infamous and horrifying dog fighting scandal that brought his career to a screeching halt and forever tainted his legacy.

Before his 2007 conviction (resulting in a 21-month prison term) and 2008 bankruptcy, Vick racked up some major achievements. In 2001, he was selected first in the NFL Draft, becoming the first African-American quarterback to earn that honor. He reached the playoffs twice with the Atlanta Falcons, and made three Pro Bowl rosters.

And then it all fell apart.
What Happened: Three threads led to Vick’s financial downfall. First, he spent money freely during his early career. According to ESPN, he earned nearly $40 million per year at his peak, an outrageous rate even for a top-tier NFL quarterback. But he also helped out some 30 family members and associates, some lavishly – for example, Vick’s younger brother got a new car every year on his birthday. He made some poorinvesting decisions too, including a $1.6 million bet with a business partner who used his money to buy cars and inflate his own salary.

Secondly, Vick ran a sophisticated and brazen interstate dog fighting ring out of his Virginia property for five years. Dog fighting didn’t cause Vick’s financial troubles, but they came to a head when authorities found out what was going on. After his conviction, his earning power crumbled.

Thirdly, even as Vick racked up wins on the field, his first agent was aggressively pursuing a $45 million lawsuit stemming from a 2001 contract dispute. The parties finally settled $4.5 million in 2008, shortly before Vick declared bankruptcy. According to ESPN, Vick may have been able to avoid bankruptcy had the agent not demanded full payment right away. As it happened, Vick filed his bankruptcy petition in 2008, listing assets of less than $50 million against debts of up to $50 million. Vick lost most of his physical assets in the ensuing proceedings, and the Atlanta Falcons added insult to injury by clawing back approximately 20% of Vick’s $37 million signing bonus.
Post-bankruptcy Activities

When Vick finished the house arrest term that followed his prison sentence, the Falcons released him, and it was not clear that he’d ever play in the NFL again. He eventually landed with the Philadelphia Eagles, playing backup to veteran QB Donovan McNabb.

During the 2010 season, after the Eagles traded McNabb and his replacement was injured on the field, Vick stepped into the starting role. The rest of the season was an unmitigated success, with the Eagles going 10-6 and making the playoffs. Vick signed a six-year, $100-million contract (with $40 million guaranteed) the following year.

Vick’s performance dropped in 2011 due to persistent injuries. He lost the starting job in 2012, briefly regained it in 2013, lost it again due to injury, and was traded to the New York Jets in 2014. He earned $5 million with the Jets that year, but played just a few games. In 2015, he went to the Pittsburgh Steelers, and shortly announced that he’d retire at the end of the 2016 season.
What We Can Learn: Vick made a strikingly poor choice as a young man and lost tens of millions in future earnings as a direct result. He also struggled to say “no” to friends and family who asked him for money or favors, and did not properly vet potential investments and business opportunities. He squandered much of his fortune in the process.

That said, Vick’s comeback was heartening. He showed what appeared to be genuine remorse for his actions and was rewarded with a second chance to play the game he loved. His reputation has improved somewhat, despite the lingering ethical stain. And, from a financial perspective, he’s far from destitute.

According to Business Insider, Vick passed $100 million in career earnings in 2014, though it’s impossible to say exactly how deeply his draft day earning potential was eroded by the dog fighting episode. Vick’s experience is a reminder that financial troubles don’t have to be permanent, especially when we overcome the circumstances that cause them.
4. Curt Schilling: The former Boston Red Sox ace, whose on- and off-field antics divided his fan base long before his financial troubles, is an interesting case. After helping the Red Sox win the 2004 World Series and erase the team’s 86-year championship drought, Schilling didn’t simply whittle away his baseball fortune – he also bilked the state of Rhode Island to the tune of $75 million.

Long an avid computer gamer, Schilling founded a small game development company in 2006, and deepened his involvement after retiring in 2009. Known as 38 Studios, the company announced ambitious plans to develop a “massively multiplayer online role playing game” (MMORPG) in the “World of Warcraft” mold. A slimmed-down version of the game, titled “Kingdoms of Amalur: Reckoning,” debuted at Comic-Con 2010.

Schilling was on his way to a glorious second act. Or was he?

What Happened: 38 Studios’ high-profile leader, a well-regarded (if not uniformly beloved) New England sports icon who famously won Game 6 of the 2004 American League Championship despite a bloody ankle injury, made the company’s ambitious plans easier to swallow. In 2010, the state government of downtrodden Rhode Island approved a $75 economic development loan to 38 Studios, which promised to complete its planned MMORPG and create 450 jobs in-state within two years.

Under the best of circumstances, building a rival to “World of Warcraft” in two years is an optimistic goal for any startup computer game developer, let alone one run by a retired ballplayer with no experience. Within a year, it had become obvious that poorly managed 38 Studios, which was further hampered by poor sales of “Kingdoms,” would not meet its deadline. In May 2012, per Polygon, the company failed to make a $1.1 million loan payment to the state of Rhode Island, stopped meeting payroll, and laid off its entire staff (and that of Big Huge Games, a Maryland subsidiary) by email.

The backlash was swift. Schilling, an outspoken political conservative, faced jeers for accepting and then squandering millions in state aid. The deal sparked years of litigation, eventually netting the State of Rhode Island a little more than half its initial investment, per Bloomberg. The Securities and Exchange Commission accused the state of Rhode Island and Wells Fargo, its primary financial go-between, of fraud, according to the Portland Press Herald.

Though Schilling avoided criminal penalties and personal bankruptcy, his reputation as a businessman was ruined, and his personal finances suffered greatly. According to the Toronto Star, his $50 million net worth at retirement shrank to just $1 million four years later, forcing him to sell off prized personal possessions (including the bloody sock from the 2004 ALCS).
Post-bankruptcy Activities: Schilling’s experience with 38 Studios certainly called his business acumen into question, but it didn’t hurt his marketability as a baseball expert. Already a color commentator for ESPN, Schilling deepened his relationship with the network after his bankruptcy filing. In 2014, he started working as an analyst for ESPN’s popular “Sunday Night Baseball,” though a cancer diagnosis shortly thereafter prevented him from working for much of the 2014 season.

Schilling’s cancer treatments were successful, and he rejoined the ESPN crew in 2015. He didn’t last long though. ESPN suspended him for much of 2015 after it discovered he’d shared a racially charged Twitter meme, and fired him for good in early 2016 when he shared a second offensive post.
What We Can Learn: First, Schilling’s experience reminds us that on-field success and business success require very different skill sets, especially when the business venture in question has little or nothing to do with athletics. Things may have worked out differently for Schilling had he pursued a post-MLB venture better aligned with his skills as a ballplayer.

Secondly, social media etiquette is extremely important. Schilling stuck his foot in his mouth twice in less than a year, and the second time proved fatal for his commentating career – further damaging his already diminished earning power. No matter what you do, always keep your personal and professional personas separate.

5. 50 Cent: When he burst onto the hip-hop scene in the early 2000s, the former Curtis James Jackson III was heralded for his crossover appeal and obvious talent. And his personal story was captivating, to say the least. Raised in crime-ridden New York City neighborhoods at the height of the crack epidemic, he sold drugs as a teenager and allegedly took nine bullets (though the true count is unclear, per BET) in a 2000 shooting that nearly killed him.

Over the course of his career, which continues despite diminishing returns, 50 Cent has sold more than 30 million albums and earned dozens of music awards, including a Grammy and 13 Billboard awards. At one point, he was the second-wealthiest hip hop artist in America, behind only Jay-Z.

Soon after the 2003 release of “Get Rich or Die Tryin’,” his first major-label album and most successful to date, Cent expanded into non-musical business ventures. In 2005, he headlined a successful, semi-autobiographical film named after his breakout album. He became an early investor in Glacéau, the maker of Vitaminwater, and reportedly earned $100 million when Coca-Cola bought the company in 2007.

His investment in G-Unit Films, a production company, was less successful, as was his founding investment in SMS Audio, which later faced accusations of copyright infringement for the design of its Street by 50 headphones. He was also briefly the subject of an SEC insider trading investigation and participated in a bizarre scheme to launch a line of 50 Cent-branded palladium in partnership with a South African precious metals mine.

What Happened: 50 Cent’s music sales steadily declined after peaking in the mid-2000s, along with his income. Despite scattered business successes, notably his Glacéau investment, Cent spent heavily on a lavish lifestyle featuring Rolls-Royce automobiles and the same Connecticut mansion that Mike Tyson lost a few years earlier. Like many wealthy celebrities from impoverished backgrounds, he generously supported a small army of friends and family members, including his grandfather and a former long-time girlfriend. He also gave freely to worthy charitable causes, such as HIV treatment and prevention in Africa.

Cent suffered from self-inflicted wounds as well, according to HotNewHipHop. In an act of personal retribution, he publicly shared a sex tape featuring a rival rapper’s ex-girlfriend, and was eventually forced to pay $5 million to resolve the resultant lawsuit. He also lost more than $2 million on Sleek by 50, another headphone venture, and was then hit with a more than $17 million judgment for allegedly stealing the design for that product. Though the exact extent of his losses and subsequent recoveries are unclear, he has publicly stated that he lost millions in the stock market during the 2008 financial crisis.

All told, Cent racked up more than $20 million in liabilities against assets of less than $15 million. In 2015, he declared bankruptcy in an effort to restructure and slim down these obligations, losing much of his fortune in the process. Notably, Cent was forced to part with his Farmington estate, following in Tyson’s illustrious footsteps.
Post-bankruptcy Activities: The jury is still out on 50 Cent’s post-bankruptcy activities. As his musical career declined, Cent devoted more attention to film work, a trend that appears likely to continue.
What We Can Learn: Going broke wasn’t the low point of 50 Cent’s life. Nearly dying in a hail of gunfire probably was. Still, Cent’s post-stardom life followed a familiar path as the rapper struggled to keep up appearances and living standards amid declining income, questionable business ventures (like trying to market his own line of palladium), and poor personal decisions.

His experience offers two lessons for anyone following in his footsteps: Have a plan to support yourself and your family comfortably when the spotlight fades, and look before you leap into sketchy business dealings or retributive acts.

Also, that house in Connecticut probably carries some sort of financial curse. If you strike it rich and settle in Farmington, buy the place next door instead.

6. Nicolas Cage: Many people don’t realize Nicolas Cage is Hollywood royalty. He’s legendary director Francis Ford Coppola’s nephew, and is related by blood to several prominent actors and directors, including Sofia Coppola and Jason Schwartzman. In his telling, he changed his name to “Cage” as a young man to avoid the appearance of favoritism.

It worked. The prolific Cage found success in a string of romantic comedies through the 1980s, then switched to dramatic and action roles through the 1990s, doggedly earning his way onto the Hollywood A-list. He pocketed an Academy Award for 1995’s “Leaving Las Vegas,” and was nominated for 2002’s “Adaptation,” though he racked up several Golden Raspberry “worst actor” awards in the years since.

Cage’s hard-charging approach to movie stardom earned him a lot of money – according to FinanceBuzz, he pocketed $150 million between 1996 (a decade after his career began) and 2011. During that time, he earned $20 million apiece for blockbusters like “Gone in 60 Seconds” and “National Treasure.” However, by 2009, much of Cage’s fortune had vanished in a hurricane of lavish spending, and the star faced mounting legal troubles that further added to his financial woes.
What Happened: Starting in the 1990s, Cage embarked on a decade-long buying spree to rival Mike Tyson’s. According to Thrillist, his many bizarre and expensive purchases included:
  • Several supercars, including a rare Ferrari and the Shah of Iran’s Lamborghini
  • Rare jewelry
  • A shark
  • A crocodile
  • Two king cobras
  • At least one dinosaur skull
  • A collection of pygmy shrunken heads
  • A private jet
  • A pyramid tombstone in a New Orleans cemetery
Cage also bought up and sold a slew of exotic real estate, including a 26-acre Rhode Island estate (then the most expensive home ever sold in the state); castles in England and Germany; a private island in the Bahamas; a “haunted” New Orleans mansion that purportedly saw a string of grisly murders in the 1800s; and a comic-strewn Southern California mansion described by the Los Angeles Times as “frat house bordello.”

Cage’s problems began in 2009, when the IRS filed a tax lien against his New Orleans home for millions of dollars in unpaid taxes dating back to the early 2000s. They accelerated later that year, when former girlfriend (and mother to Cage’s oldest son) Christina Fulton sued him for $13 million and ownership of her house, then owned by Cage. Cage also faced multi-million-dollar collection attempts by at least two financial institutions, and was hit with a counter-lawsuit from business manager Samuel Levin, whom he’d earlier sued for fraud and negligence.

Ultimately, Cage lost his California home to foreclosure, though it failed to sell at a fire-sale foreclosure auction (perhaps on account of its questionable decor). He lost a smaller Nevada property to foreclosure too, and offloaded many of his exotic personal possessions in piecemeal fashion. Not quite bankruptcy – more like non-voluntary downsizing.
Post-downfall Activities: Nicolas Cage pieced his financial life back together the only way he knew how – by working his tail off. Between 2009 and 2016, he appeared in about two dozen movies, from actual hits such as “The Croods,” to critically panned failures such as “Drive Angry.” Low standards for films such as “Drive Angry” aside, Cage seemed to judge that humiliation was preferable to destitution. And, in addition to steady film paychecks, Cage’s finances got a boost in 2011, when he sold a rare comic book for more than $2 million – approximately 20 times its 1997 purchase value, per CNN.

What We Can Learn: Nicolas Cage learned the hard way that no matter how great your earning power, how hard you work, and how vaunted your professional pedigree, you should never spend more than you can afford. That’s doubly true when, like Cage, you spend much of your fortune on supercars, exotic animals, luxury goods, and high-end real estate.

Also, while the risk of an IRS audit is low for median-income individuals, A-list celebrities with complicated financial situations need to make sure they pay their fair share of taxes. Even if they don’t pull in millions each year, taxpayers with small businesses or complex investments must be mindful of the risks associated with under-payment (or nonpayment).
Final Word

Lots of children, and a fair number of full-grown adults, dream of being famous. Celebrities seem to float above the world in privileged, perfect bubbles, avoiding the petty trials and concerns that define life for the rest of us.

The beautiful veneer of celebrity is all too often a cruel mirage. It’s hard to feel bad for people who earn millions of dollars per year and have small armies of assistants and sycophants shielding them from reality, but celebrities really do face problems that normal people don’t.

Actor Kristen Stewart told The Telegraph that being famous “is like having your limbs cut off” and makes it “logistically impossible” to perform simple public acts that most people take for granted, like going to the store. Meanwhile, Jezebel reports that performers (including actors and musicians) and athletes die five years earlier, on average, than their regular Joe and Jane counterparts. Neat explanations for public figures’ shorter life expectancies are elusive, but substance abuse and intense stress likely contribute.

If you truly have a gift for performing and believe you can handle the harsh glare of the spotlight, by all means follow your dreams as far as they’ll take you. If you like the idea of being famous, but aren’t sure you’ll enjoy the reality, a less glamorous line of work might be in order.

What’s your favorite celebrity riches-to-rags story? And what are you doing to make sure you don’t repeat the mistakes of the rich and famous?