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Mike Tyson

For a while, no boxer on earth was as feared as “Iron Mike” Tyson. The powerful puncher won his first 19 professional fights by knockout, some of which took place during the first round. He quickly became the heavyweight champion of the world, but in 1992 he was convicted of sexual assault and served three years in prison. When he got out, no amount of comeback matches could get him back his mojo, and after biting off a piece of Evander Holyfield’s ear during a 1997 fight, Tyson was disqualified. He never again won another championship.

Money shouldn’t have been a problem for Tyson. After all, according to the New York Times, he had earned more than $400 million in his boxing career. However, he had spent almost all of it, frittering it away on extravagances like mansions, luxury cars and pet tigers. He also owed $9 million for his divorce settlement and $13 million to the IRS. When he filed for bankruptcy in 2003, he claimed debts of $27 million.

Latrell Sprewell

Basketball player Latrell Sprewell first made headlines during his tenure with the Golden State Warriors. During a 1997 practice, he choked his coach, P.J. Carlesimo, and earned a 68-game suspension. Sprewell still went on to a substantial career, earning almost $100 million.

It all came to an end when he turned down a a three-year contract extension from the Minnesota Timberwolves worth $30 million. According to Sprewell, this was simply not enough money. He said, “I have a family to feed … [team owner Glen Taylor] better cough up some money. Otherwise, you’re going to see these kids in one of those Sally Struthers commercials soon.” (Sprewell was referencing ChildFund International commercials, which provided sponsorship to deprived children around the world.)

The Timberwolves’ upper management, unmoved by his family’s tragic situation, didn’t offer him one more cent, and by the end of the 2005 season, he was unemployed. By 2007, his yacht, “Milwaukee’s Best,” had been repossessed by federal marshals after missed payments and insurance worth over $1 million. In 2008, he defaulted on the mortgage on his Milwaukee home, sending it into foreclosure. His Westchester mansion went into foreclosure two years later.

Lenny Dykstra

Lenny Dykstra was a three-time All-Star player who graced the rosters of both the New York Mets and the Philadelphia Phillies. Nicknamed “Nails” by fans and seemingly never photographed without a thick wad of chewing tobacco lodged in his jaw, he helped lead the Mets to their 1986 World Series victory.

After retiring, he embarked on a new life as a financial guru, but by 2009, his free-spending lifestyle had caught up with him, and he was so broke that he sold his World Series ring. He ultimately declared bankruptcy, and in the filing he claimed $50,000 in assets and $50 million in liabilities, including money owed to both Bank of America and JPMorgan Chase.

Lawrence Taylor

Lawrence “L.T.” Taylor is considered one of the all-time NFL greats. The former New York Giants linebacker was drafted in 1981 and began winning awards almost immediately, including three Defensive Player of the Year awards and a 1986 Most Valuable Player award. He was also part of the “Big Blue Wrecking Crew,” the formidable Giants defense that made their Super Bowl victories possible.
Taylor filed for bankruptcy in 1998, literally to keep a roof over his head. According to the Daily News, Taylor was a full year behind on his mortgage payments at the time of the filing. However, his record on the field always spoke for itself, and his financial woes didn’t stop him from being inducted into the Pro Football Hall of Fame in 1999, just one year after declaring bankruptcy. His personal troubles didn’t end there, however, with a traffic-related arrest in 2009 and statutory rape charges during a 2010 trial. He was sentenced to six years probation and had to register as a level one sex offender in 2011

Michael Vick

Philadelphia Eagles quarterback Michael Vick is almost as well known for his activities off the field as he is for his achievements on the it. Prior to joining the Eagles, he played for the Atlanta Falcons, who had signed him to a record $62 million six-year contract, as well as a $3 million signing bonus. Then, three years later, he signed a ten-year extension worth $130 million, making him the highest-paid player in the NFL.

Everything seemed to be smooth sailing for Michael Vick until he went to prison for his participation in an illegal interstate dog fighting ring in 2007. The prison sentence sidelined him for almost two years, and during that time he lost his regular NFL salary and all of his endorsements, including a lucrative Nike sponsorship. The lack of income, combined with his own financial mismanagement, forced Vick to declare bankruptcy from federal prison.

Marion Jones

Marion Jones started out as one of the most inspiring stories of the 2000 Summer Olympics in Australia. A track and field athlete, she walked away from the competition with three gold medals and two bronze medals, an unprecedented achievement for a female athlete. However, her ex-husband testified under oath that he had seen her inject steroids into her stomach during the games, and she denied the allegations to both the press and to two grand juries.

Jones eventually confessed to using performance-enhancing drugs in 2007, and it cost her dearly. Not only was she forced to forfeit all of the medals she had won in Sydney, but she was also sentenced to six months in prison. Just a few years earlier, she had earned as much as $80,000 per race, as well as $1 million in endorsements. But now her finances were decimated by legal expenses, and not only was her $2.5 million home in North Carolina foreclosed, but she was forced to sell her mother’s house as well.

Jack Clark

Jack Clark played for several baseball teams between 1975 and 1992. Also known as “Jack the Ripper,” he played for the San Francisco Giants, the St. Louis Cardinals, the New York Yankees, the San Diego Padres and the Boston Red Sox. However, in 1992, during his second year with the Sox, he declared bankruptcy, listing debts of almost $7 million, including $400,000 in Federal and state taxes.

When Clark listed his assets in the filing, he cited 18 luxury cars, including a Ferrari, a Rolls Royce and a Mercedes Benz. He owed money on all but one of them. Apparently, Clark quickly got bored with his collection, and when that happened he would just get rid of the ones he no longer cared for and replace them with new ones. The habit ended up costing him his home, which was worth more than $2 million.

Source : CNBC.COM