Mike Tyson
Estimated losses: $300-400 million
Iron Mike’s fall from grace included domestic violence, the death of his father-figure trainer, a nasty divorce, a federal rape charge, felony possession of drugs, a DUI and, of course, the ear-eating incident. And after the dust settled on his lawyer fees, court settlements, alimony payments and a stupidly extravagant lifestyle (like splashing out on a US$2m bathtub and owning pet tigers), the great boxer was skint. Tyson is now making a slow recovery, but at one point he was worth less than US$700.


John Arne Riise
Estimated losses: $20+ million
Despite earnings topping $85,000 a 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.


Evander Holyfield
Estimated losses: $250 million
He had a deal with Diet Coke, a video game, the “Real Deal” record label, the “Real Deal” grill, and appeared in numerous TV shows and several films. Then, there was the Dancing with the Stars cameo. Gotta wonder how Holyfied found time to lose money. The answer: children — Holyfield fathered 11 of them, and ever since Tyson took a chunk out of his ear, it seems everyone’s wanted a piece of the champ.


Scott Eyre
Estimated losses: $10 million
Like several pros, the major league baseball pitcher had his money tied up in the US$8 billion fraud allegedly perpetrated by Texas financier Robert Allen Stanford. Eyre told the New York Post that 99 per cent of his fortune was frozen and possibly gone. After admitting that he was broke, his team the Philadelphia Phillies agreed to advance Eyre a portion of his US$2 million salary.


Alex Higgins
Estimated losses: $5.25 million
The 61-year-old, who won snooker’s world title in 1972 and 1982, is said to have been living on baby food after losing his teeth from radiotherapy while battling throat cancer. Now relying on friends and donations to fund his teeth implants so he can eat again, the former champ has lost so much weight that he can’t lift a pool cue. A longtime friend of Oliver Reed’s, he currently lives in sheltered housing in Belfast and has suffered long-term problems with alcohol and smoking since last winning the World Snooker Championship.


Deuce McAllister
Estimated losses: $70 million
If McAllister assumed that once he was out of the NFL he’d never get hit hard again, he was wrong: another victim of bad business strategies, his car dealership recently went under with debts of more than US$6.6 million, owing more than US$300,000 in interest alone. He’ll still have the NFL pension, but it won’t be enough to cover his debts and the smart money is on him seeking bankruptcy protection sometime later in the year. 


Marion Jones
Estimated losses: $60 million
Once the queen of athletics, Marion Jones hit a series of hurdles when a steroid scandal was followed by rumours of counterfeiting, forging, perjury, 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 six months in the big house. 


Lenny Dykstra
Estimated losses: $25 million
Former Major League star Lenny “Nails” Dykstra was seen as the second coming of Magic Johnson in the business world; a former athlete whose success had transferred to his business dealings. But after his magazine The Player’s Club folded, the rest of his assets began to fail as well. According to Dykstra’s July 2009 bankruptcy filing, he owed more than US$30 million to creditors, including his US$18.5 million purchase of former hockey great Wayne Gretzky’s home, which his ex-wife and children now live in. Although word of Dykstra living out of his car in California at one point is true, he is now attempting to slowly rebuild his once-robust empire.


Latrell Sprewell
Estimated losses: $96 million
Hindsight must be especially painful for former NBA Star Latrell Sprewell. He famously turned down a three-year $21 million contract with the Minnesota Timberwolves because he said it wasn’t enough money to feed his family. Within a year he had lost his $1.5 million yacht, and his house went into foreclosure. But don’t blame Sprewell for turning down the contract, though. We mean really, who could live off a measly $7 million a year?


Scottie Pippen
Estimated losses: $120 million
Why a retired athlete needs a $5.3 million corporate jet is lost on us, but apparently it was a necessity for former Chicago Bulls great Scottie Pippen. Known more for his on-court defence than his off-court acumen, Michael Jordan’s number two lost most of his cash due to poor financial planning and bad business ideas. After unsuccessfully suing his former law firm for losing US$27 million of his money through poor investments, it was revealed Pippen was unable to meet all his financial obligations and may need to play again to pay his bills. He should consider himself lucky: at least he never fluttered with running mate Jordan, whose gambling addiction was notorious.


Kenny Anderson
Estimated losses: $60 million
After filing for bankruptcy in 2005, it became clear how the former All-Star guard managed to squander a US$60 million nest egg. Spending US$41,000 a month, Anderson was paying child support for eight kids, his mother’s house bills, and the repayments on the eight cars he kept in his Beverly Hills home. But it wasn’t all footing bills for the former baller; he also set himself a $10,000 “hanging out” monthly allowance. Finally, he lost $5.8 million in a prenup agreement. Anderson, it seems, could not hold on to a dollar if it was taped to his forehead.