Top 10 Athletes Who Quickly Went from Riches to Rags

Tags: #Maradona ,   #alleniverson ,   #MikeTyson

Dan N. Scarborough

Dan N. Scarborough

Last updated:  2023-05-13 18:00:08

The same depressing tale—an athlete who is a millionaire loses everything—has been told often. To people like us, the situation seems absurd. How the heck is it possible for someone to throw away millions? Yet, according to the statistics, 60% of former NBA players experience financial hardship once they retire. Furthermore, this percentage rises to 78% for NFL athletes. These days, it seems more like an epidemic than a fad. Here are the ten most extreme examples of athletes who went from making millions to scrounging for peanuts.

10. Latrell Sprewell

A wasted opportunity will haunt him for a lifetime
Sport: Basketball
Best known for: Choking his head coach in Golden State Warriors
Reason: Greed
Amount of Regret: Moderate 

His words will be remembered forever! The Minnesota Timberwolves offered the experienced NBA player a three-year, $21 million contract in 2004. Yet, Sprewell famously turned it down, saying he needed more cash to "support his family." Then, throughout the following year, he and his agent mysteriously rejected each offer, alleging they were well below his talent level. 

Consequently, Sprewell was out of the league and totally broke a few years later. Thus, he could not pay his mortgage, and his yacht was seized and sold at a public auction. Even though hindsight is 20/20, we wonder what Sprewell is contemplating right now.

9. Dorothy Hamill

Awesome ice skater, but not so lucky with money
Sport: Ice Skating
Best known for: 1978 Olympic Gold Medalist
Reason: Business, Medical, and Legal Fees
Amount of Regret: Moderate

Ice skating star Dorothy Hamill saw great success during the 1970s. Dorothy participated in the Olympics in 1978 and won the gold medal. As one of the most recognizable skaters in history, she later accepted a position with the renowned Ice Capades in the 1980s.

Sadly, despite all the money Hamill made from her career, endorsements, and other endeavors, in 1991, she declared chapter 11 bankruptcy and was in a desperate financial situation. She had invested a lot of money in several businesses and later spent more on legal fees to get custody of her daughter, on fighting depression, and on medical expenses after learning she had breast cancer.

8. Travis Henry

Womanizing has its price, and the price is high
Sport: American Football
Best known for: One-hit-wonder season (2002)
Reason: Child support for a smaller village
Amount of Regret: Substantial

Eleven children with ten different women? That will only lead to financial catastrophe. The worst part is that Henry, who had a relatively brief NFL career from 2001 to 2007, never amassed superstar-level wealth, earning only $20 million. 

In 2009, Henry's attorney calculated that he should pay around $170,000 a year in child support. However, things only became worse. Thus, he spent two years in jail and was charged with federal drug charges for selling cocaine.

7. Sheryl Swoopes 

String of bad decisions overall ruined her life
Sport: Women's Basketball
Best known for: Being the face of the WNBA
Reason: Bad management
Amount of Regret: Substantial

Sheryl Swoopes earned an estimated $50 million throughout her professional tenure with the WNBA. Swoopes was one of the most prominent figures who represented the league. She won four WNBA titles and has three Olympic gold medals.

Yet, her enormous wealth did not last her entire life. She alleges to have had poor representation, made flawed investment decisions, and contributed to her financial loss. Swoopes ultimately had to sell her Naismith trophy and Olympic medals to pay off her debts, including a $250,000 tax bill.

6. O.J. Simpson

One rash decision can turn your life over
Sport: American Football
Best known for: The murder trial
Reason: Legal fees
Amount of Regret: Substantial

If the name is unfamiliar to you from professional football, you are likely familiar with it from the century's biggest murder scandal and trial. Simpson was accused of killing his ex-wife and her boyfriend, Ron Goldman.

He had an $11 million net worth, but for obvious reasons, most of it vanished during the trial. Even though he was ultimately cleared of all murder charges, he was found guilty of the crimes in a civil lawsuit. Thus, he was forced to pay the Goldmans $33.5 million in compensatory and punitive damages.

5. Allen Iverson

The Answer planned his future, thankfully
Sport: Basketball
Best known for: Terrific scoring ability
Reason: Overspending
Amount of Regret: Moderate

He was referred to as the "Answer" at his peak. Still, the small-framed former Philadelphia 76er couldn't find answers for his financial problems. Iverson reportedly made over $250 million during his career, primarily from endorsement deals and his contracts with the Philadelphia 76ers. 

However, some early foresight might be "A.I's" savior. He reportedly has $32 million in the bank, which he can only access fully once he is 55. Until then, he receives $1,000,000 a year.

4. Antoine Walker

Walker earned everything by playing brilliantly
Sport: Basketball
Best known for: Winning a title with Miami Heat
Reason: Overspending
Amount of Regret: Massive

Antoine Walker had an excellent college career before entering NBA. During his days with Boston Celtics (1996-2003), he was one of the most productive power forwards in the league. His excellent scoring ability, solid rebounding, assisting, and three-point shooting made him an NBA All-Star. In his later years, he was still a golden substitute and an essential factor when Miami Heat won their first NBA title in 2006. Thus, his career earnings topped close to $110 million. However, things quickly went downhill.

Walker did the worst possible things by buying houses, cars, and jewelry and even supported tens of his friends and family members. Yet, he reached the bottom once he was arrested for writing bad checks while gambling in Las Vegas. Incredibly, only two years after his retirement, he filled for bankrupcy! Luckily, Walker bounced back, but he'll never have the riches he once threw away.

3. Mike Tyson

Tyson didn't have much luck with money and women
Sport: Boxing
Best known for: The youngest heavyweight champion in history
Reason: Divorce and overspending
Amount of Regret: Big

Fans and fellow boxers alike used to tremble at the mere mention of "Iron Mike." Still, when he declared bankruptcy in 2003, he may have been the only one feeling threatened. It's hardly surprising that Tyson's alleged $300 million career earnings were lost due to his expensive divorce and love of exotic animals, including tigers.

But Tyson has made a resurgence! His book "Undisputed Truth" has done well, and he looks to be doing much better these days with his movie cameos and public appearances. Also, his legal marijuana business is thriving.

2. Diego Armando Maradona

Maradona couldn't swerve IRS
Sport: Association football
Best known for: One of the best football players ever
Reason: Tax evasion
Amount of Regret: Massive

Diego Maradona, one of the all-time great soccer players, competed in four World Cups. With the most contentious goals ever scored in history, he finally won the title in 1986. Unfortunately, Maradona had a habit of not paying taxes. 

The Italian Tax Authority caught up to him in 2009 and asked that he pay $54 million, which was beyond what he could afford. Therefore, Maradona was forced to file for bankruptcy, which put him in dire straits. Thanks to his god-like status, he still recovered and even led Argentina to a World Cup as a coach.

1. Evander Holyfield

He probably regrets it now, but it seemed like a good idea at that moment
Sport: Boxing
Best known for: Being the undisputed heavyweight champion
Reason: Child Support and Overspending
Amount of Regret: Hella

Evander has been eating away at his checking account since Mike Tyson chewed off a piece of his ear in 1997. Holyfield, a former heavyweight champion who bought a 109-room mansion and earned over $230 million during his career, is a pretty broke man. 

Oh, and his mansion was seized and sold at an auction. What is the main reason for his financial troubles? Child support. Evander Holyfield has sired 11 kids with six different partners. Therefore, that's the reason why he fought until his 50th birthday.

Professional athletes who run into financial difficulties have a few elements in common. This includes a limited earning window, a lack of financial literacy, and overspending. Most other people have careers that last 30-50 years and also seek help from financial experts to manage their wealth. Conversely, athletes have short careers and often overspend, making their lives hell.

What's your favorite (or least favorite) fall from financial grace in sports? Which athletes would you add to the list? 

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