At his peak, Michael Vick ruled the NFL. The Atlanta Falcons quarterback was, at the time, the highest-paid player in professional football. However, he ran into legal troubles that eventually spiraled into financial ones as well.
After he was caught and convicted of participating in a dog fighting ring, Vick spent 21 months in prison. Because of this, he lost his job and many of his lucrative endorsements, leading him to declare bankruptcy while still in jail.
Dorothy Hamill was an Olympic ice skater, whose biggest legacy probably ended up being her iconic bowl haircut. Despite her gold medal wins and massive popularity, Hamill eventually found herself in dire financial straights
In 1996, the press reported that Hamill was filing for bankruptcy. While specific reasons were not given, Hamill vaguely described her decision as the result of poor investment advice and bad management.
Whether you love him or hate him, it’s truly unreal that Mike Tyson has managed to keep the public’s attention despite a sexual assault conviction and light case of cannibalism. But, like so many sports superstars, Tyson has had his fair share of money problems.
Things finally came to a head for the boxer in 2003, when he declared bankruptcy. Despite the fact that he was still making millions at the time, his debt was also in the millions.
Tom Brady is easily one of the most recognizable football players that have ever existed. He’s quietly broken records for years and years, earning a massive salary of $25 million per year. Actually, at his highest, he made more than $40 million (in 2021). Unfortunately, that sum dropped dramatically this year.
Tom Brady announced that he was going to retire, and everyone was up in arms. Then, just as soon as he retired, he unretired, but that resulted in a much lower salary of $8 million. That’s a major hit. For a rich person, that basically is like going broke. After all, he’s married to Gisele Bundchen, so they have a hefty expense report combined. Guess he saw his retirement as a definite “going broke.”
Warren Sapp was a professional footballer who played for the Buccaneers and Raiders in the '90s and early 2000s. Sapp was infamous for his bad attitude and rough play style. After his retirement, Sapp became an analyst for the NFL channel, and that’s where his money problems began.
In 2010, a lien of $33,000 a month was placed on his paycheck. Reports showed that he owed almost a million dollars to the IRS, as well as unpaid alimony and child support.
Marion Jones is an Olympic sprinter who, these days, is probably more infamous than just plain famous. Years after winning multiple gold medals in the 2000 Olympics, Jones confessed to using steroids and was stripped of her awards.
She found herself in more legal trouble when she was implicated as a part of a check-cashing scheme with her former boyfriend. Jones eventually spent time in jail where she would declare bankruptcy.
Let’s get real--is anyone surprised that a guy like Dennis Rodman has money problems? The bombastic and flamboyant NBA star has a penchant for going above and beyond.
Court proceedings would later reveal the extent of Rodman’s financial woes. It was revealed that he owed almost $1 million in unpaid child support and over $50,000 in unpaid spousal support.
During his time in the NBA, Allen Iverson was one of the highest-paid professional athletes in the world. But even a $21 million dollar salary couldn't keep him from money problems.
When his wife filed for divorce in 2010, it was revealed that Iverson was in serious financial trouble due to debt and frivolous spending. He should be okay if he can hold out until 2030--that’s when he’ll be able to access a $30 million trust fund from Reebok.
No list of football legends is complete without the famous Dan Marino. We can go on and on about his memorable highlights, but instead, we're going to talk about another time in his life that stood out...but not in a good way. After retirement, Marino stayed active by being a sportscaster and analyst.
Along with that, he also tried to invest in some new stuff. That's where his losses came in. Marino saw how the 2Pac hologram at Coachella blew everyone away, so he invested in Digital Domain. Not long after Coachella, the company tanked, and Marino lost all of his dough.
Antoine Walker spent over a decade dominating both the college and professional basketball scenes. When all was said and done, Walker had earned over $100 million at retirement.
However, his frivolous spending meant that Walker eventually found himself in money trouble. The former athlete was arrested in 2009 for writing bad checks in Las Vegas to the tune of $1 million.
Among hockey fans, Bobby Orr is considered one of the greatest of all time. While he may have been great on the ice, he was not great with his money.
Despite being one of the highest-paid hockey players at the time, Orr still found himself facing bankruptcy thanks to some shady dealings of his agent at the time. Eventually though, Orr managed to get his finances back on track and seems to be doing fine in retirement.
Lenny Dykstra was at the top of his game as a professional baseball player for both the Mets and the Phillies. Even up to 2008, Dykstra appeared to be wealthy and doing fine. But that all changed in 2009.
In that year, he filed for bankruptcy, claiming that he had been swindled with mortgage fraud. Things got even worse and weirder when, in 2012, he was arrested for bankruptcy fraud relating to his 2009 claim.
Johnny Unitas had a two-decade NFL career from the '50s to the '70s. His time on the field included multiple MVP wins, as well as other honors.
However, by 1991, things were not looking good for the former player. It was this year that he and his wife would file bankruptcy in an attempt to prevent collection on over $4 million dollars in loans, which Unitas was unable to pay.
Sheryl Swoopes made millions and history when she became the first WNBA player to have a Nike shoe named after her. Unfortunately, Swoopes would go on to lose everything she worked for.
After some bad investments and poor management, Swoopes was forced to declare bankruptcy in 2004. Her financial troubles only got worse from there--when she was let go from her WNBA team in 2009, she apparently couldn’t even afford to pay rent.
NHL players are not necessarily the richest, but hockey pro Darren McCarty still managed to bring in over $15 million over the course of his career. Unfortunately, McCarty didn’t seem to be able to manage his massive wealth.
McCarty lost it all thanks to drugs and gambling, and eventually filed for bankruptcy in 2006. Later, he would have even more trouble with the IRS thanks to unpaid taxes.
Former NFL star Antonio Brown has filed for Chapter 11 bankruptcy, reportedly owing nearly $3 million to various creditors. This move follows a series of legal and financial troubles for Brown, including multiple lawsuits for unpaid debts.
One notable case involves a jeweler, Shuki International, who claims Brown owes him $1.1 million for several pieces of jewelry. Brown had agreed to pay for these items by December 2022 but failed to do so, leading to the lawsuit.
Terrell Owens was an NFL wide receiver from the late '90s to the early 2010s. It’s estimated that he earned over $80 million in his decade-plus football career.
Of course, like most everyone else on this list, Owens would eventually file for bankruptcy. He listed investments, the housing market, and child support payments as reasons for his filing.
Vince Young was once the star quarterback for the Tennessee Titans. When he was drafted as a rookie, he even managed to nab one of the highest rookie salaries in NFL history. But, as his financial advisor put it, Young was spending money faster than he was making it.
Much of Young’s wealth was spent on frivolous purchases, and, to no one’s surprise, he found himself in bankruptcy court. According to filings, his assets were valued at up to $1 million, while his liabilities topped $10 million.
There aren’t many superstars from the golf world, but John Daly is absolutely one of them. Despite being one of the highest-paid athletes in the sport, Daly still found himself in financial trouble.
Unlike some, the golfer has been frank about what caused his issues--gambling. The world was shocked when he revealed that he had lost more than $98 million from gambling alone.
You know you’ve had some kind of life when your financial scandals are laughable compared to some of the other things you’ve done. And not many besides OJ Simpson can say that.
The former football player was charged with murder in the '90s, and while he was found not guilty, lawyer fees and an additional civil suit left him struggling for money. He would eventually be forced to pay the Goldman family over $30 million dollars.
Diego Maradona was once one of the world’s most popular soccer players. He was even named Player of the Century by FIFA in 2000. Despite his bringing in millions, I bet you can guess what happens next.
Apparently, Maradona owns a lot of money to the Italian government for his time as a player for the Napoli team in the '80s and early '90s. Specifically, his unpaid bill tops $50 million dollars.
Professional athletes weren’t paid as much in Leon Spinks’ day, but the boxer still managed to make millions during his career from 1977 to 1995. Nevertheless, the Leon Spinks of today is a far cry from the man he once was.
Due to drug use, frivolous purchases, and legal problems, Spinks squandered most, if not all, of his fortune. He keeps a low profile these days, but he was rumored to work as a janitor at a YMCA.
When it came to hits, not many were better than former MLB player Jack Clark. By the end of his career, he had racked up thousands of runs and stolen bases. After his retirement, he would go on to rack up a lot of debt.
Clark had a love for luxury cars and often spent more than he should on them. During his bankruptcy proceedings, it was revealed that when he was done with one car, he’d simply get rid of it and buy a new one. At the time, he lost almost everything, including his home, but he’s also managed to make an impressive comeback financially after his problems.
Lawrence Taylor played for the New York Giants in the '80s and '90s, and he’s considered by some to be one of the best defensive players of all time. He began using drugs shortly after joining the NFL, and they would eventually cause problems for him, financial or otherwise.
In addition to his other legal problems, Taylor pleaded guilty to failure to pay taxes. This, coupled with bad investments, meant lots of financial hardship for the former footballer.
From 2001 to 2007, Travis Henry played football for several NFL teams. Despite the high salary that comes with professional gigs like these, Henry has struggled to stay afloat.
Most of his money problems stem from child support payments for his nine children. According to estimates, he owes over $150,000 in support per year and was behind by at least $16,000. He was eventually sued for this in 2009.
It’s not just American athletes that struggle with money issues. Just ask Norwegian soccer player John Arne Riise.
While playing for the Liverpool Football Club, Riise was declared bankrupt in a UK court for unpaid debts of over $100,000. Behind the scenes, he must have really been struggling financially, because he was estimated to make $50,000 a week at this point in his life.
Despite his name, Rollie Fingers was indeed a real baseball player with real financial problems. With three Wold Series wins, Fingers definitely made his mark on the world of baseball.
In 2007, long after his career was over, it was reported that Fingers owed millions to the state of Wisconsin because of unpaid taxes. It was one of the largest delinquencies in state history. Thankfully, he eventually got it squared away, but that $1.4 million check must have hurt to write.
Deuce McCallister played football for the New Orleans Saints for eight years in the 2000s. However, poor investments quickly ate into his earnings.
His home was seized because of unpaid mortgage payments totaling almost $2 million dollars, and he also lost a car dealership to bankruptcy as well. That being said, he seems to be rebounding--he currently owns a chain of bars and is a newscaster.
You don’t need to be an accounting whiz to see that former NFL player Mark Brunell has money problems. $5 million in assets versus $25 million in debts is never a ratio you want to have.
Brunel would eventually file for bankruptcy in 2011 after some bad business investments. His debts included real estate loans and money lost from opening up several Whataburger restaurants.
During his MLB career, Bill Buckner would play for the Cubs, Dodgers, and Red Sox. He’s one of a very few number of MLB athletes to play in four decades.
Unfortunately, Buckner would go on to have some financial problems after his baseball career was over. Once he retired, he moved to Idaho, where several financial investments (including a car dealership that closed after two years) gave him problems in the money department.
Arantxa Sanchez-Vicario was a professional athlete while most of us were still killing time in study hall. This professional tennis player won the 1989 French Open at only 17 years old! Unfortunately, her fame and fortune were jeopardized through no fault of her own.
In 2012, she revealed while she made almost $60 million during her career, her parents squandered most if not all of it. She would later sue her own father because of this, and they settled privately out of court in 2015.
Denny McLain pitched for the Detroit Tigers in the '60s and '70s. While he was a good pitcher, his mouth would sometimes get him into trouble, which ended up being a warning of things to come.
Unfortunately, during his time as a player, McLain was secretly involved with gambling and organized crime. After a Sports Illustrated expose revealed his wrongdoings, he found himself disgraced and broke.
The name Evander Holyfield is basically synonymous with boxing. Holyfield took the sport by storm, managing champion titles in multiple weight divisions. However, his fame couldn’t keep money troubles at bay.
As a retired boxer in the 2000s, Holyfield’s money problems began to pile up. He was sued for unpaid child support, as well as other debts he owed, and ultimately his $10 million dollar mansion in Atlanta was foreclosed.
John Elway is famously the President of the Football Operations of the Denver Broncos, but he lost pretty much everything after he retired from the NFL. He got involved in a Ponzi scheme which resulted in him losing half of his original investment of $15 million!
Elway was apparently the only person. Sean Michael Mueller was the one who scammed everyone out of more than $71 million. The worst part? Elway convinced a friend of his to also join in on this little scam, which resulted in him also losing some dough. He’s made that money back, but during that time? It was rough.
