MoneyINC Logo
Years of

20 Different Ways The Rich Lost Their Millions


"Here today and gone tomorrow" is a phrase that many former millionaires are familiar with. It’s entirely possible to be filthy rich one day and to end up in bankruptcy court the next. Some of the wealthiest have lost their fortunes in bizarre or unfortunate ways. Some of the declines were due to negligence with their fortunes and others were due to unfortunate circumstances, but most of these losses were preventable with a little self-control or foresight.

Hopefully as you read these stories you will learn some valuable lessons about money management.  In reality the answer is always simple.  Don't spend more money than you take in.  Unfortunately the majority of society doesn't listen to this very simple rule:

Here are 20 different ways that the rich have lost their millions.

1. Samuel Clemens - Squander and poor investment choices

Mark Twain was the pen name that Samuel Clemens used as he wrote “The Adventures of Tom Sawyer, Adventures of “Huckleberry Fin” as well as for “Pudd’n Head Wilson.” The author of these now great classics lived an affluent life that was filled with extravagant spending. He was a brilliant writer, but when it came to business, he didn’t have such a flair. He also invested money on ill-fated projects that eventually ended in his financial ruin. Prior to his filing for bankruptcy, Clemens lost ten million dollars. He invested in a Paige typesetting machine and a publishing company that lost nearly $8 million when all was said in done, but he did pass on investing in the invention called the telephone because he thought that it was an unrealistic device that wouldn’t go anywhere. Twains debts were so high by the end of his lifetime that in his last years, he was forced to engage in speaking engagements to help settle his high debt load.

2. Sean Quinn - A single poor investment

At one time, Sean Quinn known as the richest man in Ireland. His net worth was approximately 4.7 billion euros. This was his estimated net worth in 2008. His fortune was earned through his business Quinn Cement which did well, and he used profits from the company for other investments which paid off very well. He founded the Quinn group, dealing with the hospitality arena in Ireland and his net worth exploded into the billions. It was his investment in the Anglo-Irish bank that led to his financial downfall. The spiral began with the 2008 financial crisis which occurred immediately after his investment choice, and the Quinn Insurance company also took a sharp downturn. In addition to these losses, Quinn and his wealthy family were the targets of multiple lawsuits alleging misuse of funds in deals involving the Anglo-Irish bank and property loan securities. Quinn went from the net worth of 4.7 billion to a negative 3.5 billion in the debt that was amassed. He was sentenced to time in prison in addition to losing his fortune.

3. Horace A.W. Tabor - Political Act out of his control

Horace Tabor amassed a fortune in the 19th century that was over three million dollars. The American prospector was also a businessman and politician in the Republican party. He built his fortune during the time of the Colorado silver Boom. He was owner of a third of a mire that hit payload. He used the proceeds for other investments and was fortunate enough to increase his wealth yet more. He became a prominent citizen who established news, financial institutions and cultural venues. When the Sherman Silver Purchas Act passed, the fortune that Tabor had amassed was taken to zero. All his holdings were liquidated and he died in the tool shed that was located at his mine in 1899.

4. Daniel Drew - Manipulation of stock prices

Daniel Drew was an author and financier who made his fortune and lost it in the mid-1800s. He was considered one of the first great financiers of Wall street. He enjoyed years of success as his steamboat business flourished and added to his net wealth. He had amassed a fortune of $13 million prior to the decline of his estate. In 1844, he established his own brokerage firm. It was when he began to speculate on stocks that his fortune shot upwards. It wasn’t long until he was dealing with Cornelius Vanderbilt in a shady deal to prop railroad stock prices. Vanderbilt turned on him when he tried to sell the stock short and it ended badly for Drew with Vanderbilt and his cronies purchasing every available share of stock forcing a spike in the price. This continued until Daniel Drew filed for bankruptcy in 1876. At the time of his death he was living on the good graces of his son, a pauper. He could have avoided this fate by being more honest in his dealings.

5. Jack Whittaker - Bad luck

Jack Whittaker is one of the saddest cases of fortunes lost. He won $314 million in the West Virginia lottery. He paid taxes on the amount and was left with $113 million which he took out in a one- time payment. Prior to his big win, he was already worth $16 million earned through is role as President of Diversified Enterprises Construction company. Within a year of his 2002 lottery win, $545,000 in cash was stolen from Whittaker’s car which was parked at a strip club. It was broken into by thieves. Nobody knows for certain why he kept this large amount of cash in his car. Next, his granddaughter along with her boyfriend were discovered dead and each had methadone and cocaine in their systems. He was also sued by a woman that he failed to make payments to and he resorted to bouncing checks at casinos. His great fortune was totally lost in a short period of time.

6. Mark Brunell - Poor investments

Mark Brunell is best known as being a moderately successful quarterback for the Washington Redskins as well as the Jacksonville Jaguars and New York Jets. He made it to the Pro Bowl on three separate occasions. He amassed a net worth of $50 million during his time with the National Football League. Brunell made a series of bad investments that didn’t pay off and he was left with $5 million in debt. He filed for chapter 11 bankruptcy which would give him time to pay off his creditors. He lost the bulk of his money in poorly timed real estate acquisitions and loans.  Right now Brunell is coaching high school football and occasionally sits in as an NFL analyst, but he's definitely got a ways to go to get out of his debts.

7. Rick Burton - unpaid debt and taking on too much work

Rick Burton earned his fortune through his construction business which bid on large jobs. What led to his financial ruin was taking on the bid to build a private air terminal at McCarran International Airport. Hid outbid some of the larger Vegas players, but when the project failed, Burton was left with a significant amount of unpaid debt to his creditors. He declared chapter 7 bankruptcy in 2012 with a mere $6,000 in assets and just under 100 creditors. He also owed the State of Arizona $135 million for the purchase of land. He owed another $6 million to the IRS and the total amount owing was over $300 million at the time of his filing. This happened to Burton because he took on projects that he couldn’t complete and overextended his ability to reasonably complete them. It cost him everything and his fortune was lost.

8. Clint Murchison, Jr. -Bad investments and squander

Clint Murchison, Jr. is the son of Clint Murchison, Sr., the oil baron who left behind a fortune of a half billion dollars. The younger Murchison did not possess his father’s keen business sense and squandered the family fortune. He did manage to purchase the Dallas Cowboys football team which was a smart move. He was left $200 million after his father’s death. Aside from his investment in the Cowboys, he made a series of poor investment choices which included playing the real estate market. By 1985, his assets were liquidated to cover the $500 million debt that he owed. He had lost a $200 million fortune.

9. T. Cullen Davis - on trial for murder

T. Cullen Davis inherited a $250 million fortune. At one point in his life, the Texas oil heir was a billionaire, but he lost every cent of his fortune and his story is one of the darker ones we’re telling. He is the wealthiest person in the world to stand trial for murder. His wife had filed for divorce and was living with a boyfriend. Davis allegedly broke into his home in 1976 and shot them both. The 12-year-old daughter of the boyfriend was also killed and it was revealed that she was forced into the basement onto her knees and then shot in a kneeling position. Davis’ ex-wife survived and named him as the assailant. Davis was found not guilty by a jury, but he still filed for personal bankruptcy in 1986. His debts were more than $230 million. Davis was described as having a terrible temper.

10. Kim Basinger - Breach of contract lawsuit settlement

Famous American actress Kim Basinger had amassed a net worth of $5.4 million until she was sued for breach of contract. Basinger backed out of a contract that she had agreed to with Main Line Pictures and the movie “Boxing Helena.” The company sued her for $8.1 million for breaching the contract she had signed with them. The battle went on for more than three years and finally, Basinger and her attorneys settled with the sum of $3.8 million, forcing her to file for bankruptcy in 1993. Since this time, Basinger has starred in several films and has rebuilt her fortune, and today at the age of 60 years old, she has exceeded her past fortune and is now estimated to be worth $36 million.

11. Nicolas Cage - Extravagant Lifestyle and unpaid taxes

Actor Nicolas Cage was earning $40 million a year in his heyday as a film star. He enjoyed wealth and a high level of success and popularity as a mega-star. He had a fondness of the finer things in life and also had expensive tastes. He squandered his fortune on mansions, private jets, collectable sports cars and a life of luxury that exceeded the amount of his total fortune. Cage made more than $150 million in earnings as an actor between 1996 and 2011, making him among the highest paid actors in Hollywood. In addition to being sued by his former manager Samuel Levin, Cage had racked up a $6.5 million debt in back taxes. He had lost his fortune because of his expensive tastes, love of luxury and delinquency in paying his taxes.

12. Willie Nelson - Illegal tax shelter and unpaid IRS debt

Country and Western singer Willie Nelson made the news in the early 1980s when the IRS sent him one of the highest federal tax bills in history. It was discovered by IRS investigators that he had made investments in an illegal tax shelter. His total debt was $16.7 million. The debt was negotiated and then lowered to a cash payment of $6 million, but Nelson didn’t have that kind of money at the time. His Texas ranch home was raided and his assets seized because he ignored the debt instead of dealing with it. It took him until 1993 along with a lot of hard work to pay off the debt that he owed the government. Nelson has continued working and rebuilding his fortune and is now estimated to have a net worth of $25 million in an incredible bounce back from poverty

13. Jo Hale/Meat Loaf -Lawsuit settlement

Jo Hale is the legendary singer Meat Loaf who achieved tremendous success and earned multiple millions of dollars in the early 1980s. The singer’s financial woes began when Jim Steinman, the writer responsible for creating many of the successful songs that helped Hale to amass his fortune, filed a lawsuit against him. This followed on the heels of the flop of his album “Dead Ringer.” Hale lost he lawsuit and was forced to file for bankruptcy, losing a fortune in the deal, but today, he’s not doing too badly with an estimated net worth of $25 million which has come from acting and concert gigs.

14. Mike Tyson- divorce and unpaid tax debt

Mike Tyson earned fame and fortune through his 20-year long career as a professional boxer. His total earnings were $400 million throughout his career, but he didn’t make wise choices with his fortune and it dwindled away. There were a series events that took Tyson down financially. First was his divorce which cost him $9 million, next was an IRS debt of $13,4 million and an additional $4 million to the British tax authorities. Tyson filed for bankruptcy in 2003 and his total debt at the time was $23 million. Mike Tyson earned a staggering $400 million over the course of his 20-year boxing career.

15. Marvin Gaye - divorce settlement and drug addiction

Marvin Gaye was a Motown legend in the 1970s. In 1976, his first wife Anna Gordy Gaye divorced him and Gaye was ordered to pay her $600,000 in alimony. He signed over the rights to one of his albums to the ex. Much of the $5 million fortune that he made was squandered on drugs and poor financial choices. He was behind on federal taxes but relocated to Europe to avoid penalties of the IRS. Gaye died in 1984 after having a heated exchange with his father and being shot dead by him.  Gaye will go down as one of the greatest singers the world has ever seen but also one of the most tragic stories as well.

16. Dennis Rodman - child support, alimony and failure to pay debt

NBA superstar player Dennis Rodman had amassed a $27 million fortune through the salary that he earned as a professional basketball player. This was not counting the money that he made from various endorsement contracts. It was after Rodman left the NBA that his financial problems worsened. Married several times, Rodman couldn’t keep up with is court ordered child and spousal support payments. He was behind on all his debts and couldn’t keep up with all his bills. He also experienced problems with alcohol abuse and checked into a rehab facility after his 2014 trip to North Korea. He lost his fortune because of the cost of his divorces, supporting his children and not staying current with his debts. He ended up in court for a debt owed to his third wife of nearly $810,000 in back support.

17. Heidi Montag - Excessive spending spree

Heidi Montag earned fame through her appearances on the reality television series “The Hills.” During her time spent on the set of the show, she met and later married Spencer Pratt, who didn’t have a great reputation with her fans. The couple have managed to keep themselves in the limelight. Heidi has brought in a fortune in earnings that tops $10 million, but just as quickly as she has amassed her fortune, she has squandered it on things that we’re struggling to understand. The ten million that the couple had was spent on a pre-apocalyptic spending spree. They would give exorbitant tips in the amount A $200 just to have somebody open a door for them. They also gifted thousands of dollars to friends. Spencer Pratt had predicted that the apocalypse was coming and what good would all this money do them then? The two sincerely believed that there was an asteroid heading for planet earth and it would strike on December 21 of 2012. This was the supposed apocalypse that was predicted by the ending of the Mayan calendar back in the day. When the couple had expended the entire fortune getting ready for the end of the world, they ended up moving in with Pratt’s parents so they could survive because they were effectively broke.

18. Curt Schilling - Poor investments and bad health

Curt Schilling spent 19 years as a professional baseball pitcher in the MLB. He earned a total of $114 million over the life of his baseball career. Upon retirement, Schilling took a big chance. At the time, he was worth an estimated $50 million. He invested the entire amount into a video game company for which he was the founder. When the company filed for bankruptcy in 2012, Schilling was forced to liquidate their estate and many of their valuable possessions to pay what was left of the debt. This included their thee million-dollar home in Massachusetts. The entire fortune was lost, but this wasn’t the end of Curt’s problems. He was diagnosed with cancer and fought an eight-month battle, racking up high medical bills. After he recovered his health in 2014, he accepted a position with ESPN as an analyst but since that time he's been ousted due to outlandish commentary and remains a very controversial figure in sports.

19. Francis Ford Coppola - Film failure at the box office

Francis Ford Coppola, the legendary film director and producer had an estimated net worth of $52 million when he filed for his second bankruptcy. This is nothing new for big time film execs who gamble a fortune to make an even bigger fortune. The film “One from the Heart,” cost the producer $27 million to create, but when it hit the box office, it had only netter a mere $4 million, bringing in far less than he had anticipated. At the time when he filed for bankruptcy in 1992, his total debt liabilities were $98 million which nearly doubled his net worth at the time. He is still producing and directing films, and continues to make good investments with the proceeds so although he lost a fortune, he has risen back to the status of multi-millionaire. It’s hard to keep a good director/producer down, and Francis Ford Coppola is one of the greats in this industry.

20. Floyd Mayweather - IRS back taxes

Floyd Mayweather is a professional boxer who thrilled his fans with multiple high stakes wins. He has amassed a mega-fortune in his day and reportedly spent up to $75 million a year to support his lifestyle and the charities that he favors. One of the problems that led to his financial problems is that he hasn’t been as good at paying his debts as he has in spending millions of dollars each year. In 2009, Mayweather had a serious default against his credit on a car loan to the tune of $167,000. You would think that a multi-millionaire would be able to swing the payment. In 2013, he was in court filing a claim in a local bankruptcy case for $61 million. In 2014, the IRS sent him a bill for back taxes in the amount of $50 million. He sought legal counsel to weight his options with bankruptcy being one of them placed on the table.  Today however, Mayweather is literally the richest athlete on the planet having earned close to $400 million on his last to fights alone.

Garrett Parker

Written by Garrett Parker

Garrett by trade is a personal finance freelance writer and journalist. With over 10 years experience he's covered businesses, CEOs, and investments. However he does like to take on other topics involving some of his personal interests like automobiles, future technologies, and anything else that could change the world.

Read more posts by Garrett Parker

Related Articles

Stay ahead of the curve with our most recent guides and articles on , freshly curated by our diligent editorial team for your immediate perusal.
As featured on:

Wealth Insight!
Subscribe to our Exclusive Newsletter

Dive into the world of wealth and extravagance with Money Inc! Discover stock tips, businesses, luxury items, and travel experiences curated for the affluent observer.
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram