I thought this was interesting. Taken from Business Pundit:
25. Raghib â€œRocketâ€ Ismael
Notre Dame/Dallas Cowboys star; received the largest 3-year deal in football history
Estimated lifetime earnings: $20 Million
No jail time, drug charges or bankruptcy here, just bad business moves. Financial vultures bled Ismaelâ€™s riches by selling him their â€œfool-proofâ€ investments. After bypassing the NFL as the presumptive #1 pick, Ismael went to the Canadian Football League and signed the largest deal in their history.
He played two years in Canada and 10 in the NFL, earning an estimated $18 million to $20 million in salary alone. He then started to invest in a series of ventures that went bust, including a Rock nâ€™ Roll CafÃ©, COZ Records, a movie, cosmetics, nationwide phone-card dispensers, and caligraphy proverbs kiosks.
Today, Ismael does a sports talk show for the Dallas Cowboysâ€”and looks very closely at any money he makes.
24. Scott Eyre
World Series champion, pitcher for the Philadelphia Phillies
Estimated lifetime earnings: $10 Million
Eyre, like many of us, was taken for a fool during last yearâ€™s stock market/investment madness. His money grew tied up in the $8 billion fraud allegedly perpetrated by Texas financier Robert Allen Stanford. Eyre told the New York Post that 99% of his fortune is frozen and possibly gone. After admitting that he was broke, the Phillies agreed to advance Eyre a portion of his $2 million salary.
23. Evander Holyfield
4-time Heavyweight Champion of the World
Estimated lifetime earnings: $250 million
He had a deal with Diet Coke, a video game, the â€œReal dealâ€ record label, the â€œReal Dealâ€ grill, and appeared in numerous TV appearances and 3 films. Then, there was the dancing thing. One wonders how Holyfied had time to lose money. The answer: Children. Holyfield fathered 11 of them.
â€œIâ€™m not broke; Iâ€™m just not liquid,â€ 45-year-old Holyfield claimed when he narrowly avoided charges that he was around $9,000 behind in court-ordered child support payments. The banks foreclosed on his $10 million dollar home. Even a landscaping firm says the former champ owes them $500k for yard work. Ever since Tyson bit his ear off, it seems everyone wants a piece of the Champ.
22. Jack Clark
player since 1975
Estimated lifetime earnings: $20 million
When Jack Clark declared bankruptcy on listed debts of $11.4 million and assets of $4.8 million, his lawyer made a statement. â€œHe had some expensive hobbies, and I think they got ahead of him.â€
Ya think? The man owned 18 automobiles, including a 1990 Ferrari that cost $717k alone. His three customized, tricked out 1992 Mercedes Benzes cost around $125k each. All in all, he still owes money of 17 of his cars, as well as the failed drag racing course he meant to race them on. Add to that half a mil in back taxes, and you have some expensive hobbies, indeed.
21. Johnny Unitas
Hall of Fame quarterback, 3-time MVP, Superbowl champion, 10-time Pro Bowl selection
Estimated lifetime earnings: $4 million
Widely considered one the best pro football QBs of all time, Johnny Unitas set several records that may never be beaten on the football field, like 47 games with a touchdown pass in a row.
He starred in professional football before salaries were measured in millions. His yearly contracts ranged from $7,000, his first in 1956 with the Colts, to $250,000 plus a $175,000 bonus in his last one with the San Diego Chargers in 1973.
After his playing days, he made some money as a TV commentator for CBS. He also invested in tanked business ventures, including a chain of bowling establishments, a prime-rib restaurant, an air-freight company, and Florida real estate investment. He and his wife, Sandra Unitas, filed for personal bankruptcy protection in 1991 after investing in a failed Reisterstown circuit-board manufacturer. He died 11 years later with a lawsuit from his estate hanging over all of his businesses.
20. Deuce McAllister
New Orleans Saintâ€™s all-time rusher, 2-time Pro Bowl star
Estimated lifetime earnings: $70 Million
John Elway got out of the car dealership business early, but Deuce McAllister Nissan, based in Jackson, Miss., didnâ€™t fare as well. The business recently went bankrupt, with McAllister owing Nissan more than $6.6 million plus almost $300,000 in interest on his car dealership. Reports are that he will seek bankruptcy protection. If you want that new Deuce Pathfinder, you better pick it up in a hurry.
19. Bjorn Borg
11 Grand Slam titles; former #1 menâ€™s tennis player in the world
Estimated earnings: $4 million + $4 million in endorsements per year
Borgâ€™s famous Swede cool never made it off the court. After retiring from tennis, Bork overdosed on drugs. Some people speculate that it was a suicide attempt, though Borg denies it. His wife left him after that. Borg then courted a string of women, one of whom police busted on possession of cocaine. He tried launching a clothing line, but failed miserably. Years later, Borg has rebounded after starting an underwear line and a new dating site.
18. Rollie Fingers
Hall of Fame pitcher, 3-time World Series champ; last played for the Milwaukee Brewers
Estimated lifetime earnings: $8 Million
Fingers retired in 1985 and made it four years before investments in pistachio farms, Arabian horses and wind turbines took him down. He filed for bankruptcy in 1992. Creditors claimed he owed more than $4 million; he listed his assets at less than $50,000. He resolved his predicament by selling baseball cards and going back to work. In 2007, a dispute over back taxes flared up, but Fingers was able to prove he did indeed pay, and was cleared of all wrongdoing.
17. Sheryl Swoopes
3-time gold medal Olympian, 3-time MVP for the WNBA, first pro womenâ€™s basketball player
Estimated lifetime earnings: $50 Million
Swoopes, the â€œMichael Jordan of the WNBA,â€ scored her own Nike deal for the Jordan-inspired â€œAir Swoopesâ€ brand. Swoopes, a marketing machine, enjoyed a stint as the face of the WNBA, but her fortunes didnâ€™t last. She filed for bankruptcy in 2004, citing mismanagement by her agents and layers. She owed nearly $750,000.
16. Scott Harrison
First Scottish boxer to gain the World Boxing Federation featherweight title
Estimated lifetime earnings: $5 million
The pride of Scotland had problems with drinking, drugs and consequently the law. A world champion in 2003, Harrisonâ€™s life later spun out of control. In 2006, he pulled out of a fight to check into rehab.
It didnâ€™t work. The same year, police in Spain arrested him on charges of auto theft and assault. Officials stripped him of his title and his license to box for failing to show up for a fight and weigh in. Early in 2007, police arrested Harrison for valium possession, police assault, resisting arrest, and refusing to leave a pub. A few months later he was arrested again for starting a fight in a brothel. By July 2007, the ever-classy Harrison declared bankruptcy after losing his last fightâ€¦over unpaid taxes.
15. Leon Spinks
Beat Muhammad Ali for the heavyweight title; Olympic gold medalist
Estimated lifetime earnings: $4.5 million over two fights
Before he lost his second fight with Ali, Spinksâ€™ personal life slid downhill. Police arrested him four times for everything from driving the wrong way to cocaine possession. The WBC stripped him of the belt before the fight, but it went on for the WBA belt. Spinksâ€™ lawyers and managers allegedly spent or took all of his money. Thieves mugged him on the street. In 1990, he found his son shot dead inside in his girlfriendâ€™s car.
Spinks eventually worked for Mike Ditka as a Restaurant greeter. The company fired him. Most recently, he is stable and working at a gym again, only this time it is the YMCA, and he is the janitor.
14. Dorothy Hamill
Gold medalist skater; Americaâ€™s first darling Olympian
Estimated earnings: $1-2 million/year in endorsements
After receiving a gold medal in the 1976 Olympics, Dorothy Hamill became Americaâ€™s first Olympic darling. After that, her luck turned. A competing skaterâ€™s coach tried to run her over. She made a bad purchase in the dying Ice Capades franchise. She survived breast cancer, two divorces, and a gig as a Vioxx spokesperson. A final, failed investment in an Arizona ice skating rink pulled her into bankruptcy.
13. Lawrence Taylor
New York Giants MVP, sack leader, Hall of Famer, 2-time Superbowl champ
Estimated lifetime earnings: $50 million
After retiring from his superstar NFL career, Lawrence Taylor enjoyed his celebrity to the fullest. Known for cavorting with women, openly using cocaine and drinking late into the night, the former defensive end spiraled downwards after he left the league. Police jailed him three times for possession. The IRS caught him for filing a false tax return. Rumors claimed he was involved in a drug and gun ring. He finally declared bankruptcy in 1998. One year later, the Pro Football Hall of Fame rewarded him for cleaning up his act by inducting him.
12. Darren McCarty
Stanley Cup winner, 11-year Detroit Red Wings player
Estimated lifetime earnings: $10 million
McCarty declared bankruptcy after listing over $6 million in debts. He blamed his business partner for looting their company. One court filing states that MCCarty had a 20% stake in a company with one real asset: a truck stop. His partner took out a $3 million dollar loan on that one asset, then forged McCartyâ€™s signature for a $650,000 salary pull. Ouch.
11. Travis Henry
Starting running back for the Buffalo Bills, Pro Bowl selection
Estimated lifetime earnings: $20 million
Henry has 9 kids by 9 different mommas. He was just indicted on charges of cocaine trafficking. He was also just jailed after trying and failing to temporarily reduce one of his nine child-support payments, stating he could no longer afford to pay $3,000/month. He also fell $16,600 behind in payments for his child in Frostproof, Fla. His estimated yearly payments for the children are roughly $170,000.
To top off his pain, he just blew a $25 million contract with Broncos because of the narcotics trafficking thing and failed drug tests.
10. John Arne Riis
Fullback footballer for Liverpool; last played for Roma
Estimated lifetime earnings: $20+ million
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 motherâ€™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 â€œhanging out money.â€ 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 2007â€”around the same time as Pippenâ€™s failed NBA comeback attemptâ€”the Missouri Court of Appeals upheld a ruling that the player owed U.S. Bank more than $5 million in principal, interest and attorneysâ€™ fees from a dispute regarding a Grumman Gulfstream II corporate jet that heâ€™d purchased in 2001. Speculation has been that Pippen cannot withstand the lawsuits financially and needs to play again to make his bills.
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, Muhammedâ€™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. Muhammadâ€™s 8,200-square-foot lakeside estate, which boasts a custom spa and the â€œlargest residential aquarium in the Southeast,â€ 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 goinâ€™ onâ€¦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 Timberwolvesâ€™ $21 million offer to extend his contract for three years because the sum was too low. A mere three years later, federal agents repossessed Sprewellâ€™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 motorsportsâ€™ companyâ€™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 â€œkey figureâ€ 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 â€œNight Trainâ€ 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 UKâ€™s first celebrity footballers
Estimated lifetime earnings: $100 Million
A stunning 21-year career made George Best was one of soccerâ€™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, â€œI spent a lot of money on booze, [women], and fast cars. The rest I just squandered.â€
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 timeâ€“after he served 3 years in prison for rape. Once known as â€œThe Baddest Man on the Planetâ€ (he still might be), Tysonâ€™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.