Business Pundit

10. John Arne Riis

CARL DE SOUZA/AFP/Getty Images

Despite earnings topping $75,000 per week, this Liverpool soccer star declared bankruptcy in 2007 for unpaid debts. Embroiled in a dispute with his financial advisors and former agent, Einar Baardsen, over how his fortunes have been invested, the court has found evidence to link his case to a $4 million fraud investigation in Norway.

9. Kenny Anderson

NBA all-star, last played for the LA Clippers
Estimated lifetime earnings: $60 Million

Ringing up nearly $41,000 in monthly expenses, including child support to eight kids and his mother’s house payment, former NBA guard Kenny Anderson filed for bankruptcy in October 2005. How did his estimated $60 million dwindle to nothing? Easy. He kept 8 cars in the garage of his five-bedroom Beverly Hills home. He gave himself a monthly allowance of $10,000 that he dubbed “hanging out money.” He regularly handed out $3,000 to $5,000 to friends and relatives. Finally, he lost $5.8 million in a prenup agreement. Anderson, it seems, could not hold a dollar if it was taped to his forehead.

8. Scottie Pippen

6 NBA championships with Michael Jordan, forward for the Chicago Bulls
Estimated lifetime earnings: $120 Million

Pippen unsuccessfully sued his former law firm for losing $27 million of his money through poor investments. (He had earned about $110 million in salary alone over a 17-year career.) In February 2007—around the same time as Pippen’s failed NBA comeback attempt—the Missouri Court of Appeals upheld a ruling that the player owed U.S. Bank more than $5 million in principal, interest and attorneys’ fees from a dispute regarding a Grumman Gulfstream II corporate jet that he’d purchased in 2001. Speculation has been that Pippen cannot withstand the lawsuits financially and needs to play again to make his bills.

Maybe he should gamble with Jordan? No, that’s a bad idea, too!

7. Muhsin Muhammad

2-time Pro Bowl champ, Superbowl record-holder, touchdown dance pioneer, Carolina Panthers wide receiver
Estimated lifetime earnings: $20 million

Baylo Entertainment, Muhammed’s music company, is being sued by Wachovia Bank for allegedly failing to pay back $24,603.24 on a Visa Business Rewards credit card. Muhammad’s 8,200-square-foot lakeside estate, which boasts a custom spa and the “largest residential aquarium in the Southeast,” can now be had on eBay for $1.95 million, $800,000 less than he initially asked for.

6. Marion Jones

3-time Olympic gold medalist
Estimated earnings: $7 million per year

As the song goes, Ms. Jones had a thing goin’ on…with steroids, check counterfeiting, check forging, committing perjury to the IRS, money laundering and more illegal drugs. The fastest woman in the world certainly ran a lot of scams. After being indicted, she lost all her medals, went bankrupt, and served 6 months in the big house. She will stay on probation for a long time.

5. Latrell Sprewell

Four-time NBA All Star; last played for the Timberwolves
Estimated lifetime earnings: $50 million

This 13-year NBA veteran turned down the Timberwolves’ $21 million offer to extend his contract for three years because the sum was too low. A mere three years later, federal agents repossessed Sprewell’s yacht, on which he still owed $1.3 million. That was just the beginning. In early 2008, Sprewell defaulted on a $1.5 million mortgage, lost his home to foreclosure, stopped paying his motorsports’ company’s bills, and then defaulted on another home loan, this one worth $10 million.

4. Michael Vick

#1 overall pick NFL Draft, 3x Pro Bowl QB for the Atlanta Falcons
Estimated lifetime earnings: More than $130 million

Yes, the NFL pays well, but so do Nike, Coca Cola and the countless other companies Vick shilled for. At one time he was reportedly one of the 10 richest athletes in the world, scoring a spot on the Forbes 100 list.

Within two years of making that list, Vick found himself pleading guilty to being a “key figure” in an unlawful dog-fighting ring for more 5 years. He filed for bankruptcy. His two homes are now for sale. Vick will complete his federal prison sentence on July 20th, 2009, just in time for summer NFL camps.

3. Dick “Night Train” Lane

14 yr NFL vet, Hall of Famer, Oakland Raiders defensive back
Estimated earnings: $5 million

Once married to Dinah Washington, Lane lived the high life, complete with drugs and booze. Investments in real estate, the music business and overseas scams took what little money he had left over from after binges. After losing his fortune, he survived on $800/month pension checks, crippled by old NFL injuries. He spent his final years in an assisted living facility without any help or care from his three sons or ex-wives. A man he met on a golf course took care of him until he died, penniless, in 2002.

2. George Best

Euro Cup winner with Manchester United, one of the UK’s first celebrity footballers
Estimated lifetime earnings: $100 Million

A stunning 21-year career made George Best was one of soccer’s worldwide heroes. After the spotlight lifted, he fell so deeply into the drink that he eventually needed a liver replacement. He served 3 months in prison for drunk driving and assaulting a police officer. Then he did the same thing again, resulting in another prison sentence.

While recovering from his transplant, he appeared on the BBC, where he openly swore. When asked about his losses, he said, “I spent a lot of money on booze, [women], and fast cars. The rest I just squandered.”

1. Mike Tyson

Undisputed heavyweight boxing champion of the world, youngest man to ever win the WBC, WBA and IBF Heavyweight Titles. First man to win 12 of his first 19 fights in the first round by KO.
Estimated lifetime earnings: $300-400 million

Ring Magazine ranked Mike Tyson the #16th greatest fighter of all time–after he served 3 years in prison for rape. Once known as “The Baddest Man on the Planet” (he still might be), Tyson’s fall from grace included a sordid 20/20 interview in which his then-wife accused him of domestic violence, the death of his father-figure trainer, a nasty divorce, that federal rape charge, felony possession of drugs, a DUI, and a bloody ear incident.

At one point, Tyson was worth less that $700 dollars. But his situation has improved. He appears to be doing well in recovery for drug and alcohol problems. A movie about his life scheduled for release in 2009.