Turning to your favorite athletes or former sports star for financial advice might seem to make sense – they deal with a lot of numbers and stats all year long – but trust us, they are hardly the ones to seek out.

Blessed with millions of dollars at a young age, professional athletes often seem more concerned with inane spending and unwise investments than savings accounts and 401Ks. And that doesn’t even mention their tax return mistakes, of which there are enough to make Timothy Geithner embarrassed. From fleets of cars to yachts to entourages to even Bengal tigers, the ways some athletes chose to spend their money is comical at best and ignorant at worst.

In August of 2007, a federal marshal seized Latrell Sprewell’s $1.5 million yacht (famously named “Milwaukee’s Best”) after Sprewell had failed to pay his mortgage on the boat. He also lost his house, and now the state of Wisconsin has filed a lawsuit for unpaid taxes. This all, of course, comes after Sprewell turned down a three-year, $21-million contract, saying, “I have a family to feed.”

Some atheletes prefer to travel extravagantly by land instead of sea, however. Take former Red Sox slugger Jack Clark, for example. One story says Clark was once on his way to the ballpark for a game when he passed a car lot. Clark saw something he liked and dropped in to buy two sports cars for $90,000 each before continuing on to the game. At the time he filed for bankruptcy, Clark still owed money on 17 of his 18 automobiles.

Clark and Sprewell lost their fortunes in a hurry, but perhaps there’s no faster fall from grace than Michael Vick. In 2006, Sports Illustrated estimated that Vick made $25.4 million. Now, he owes well over $10 million to a variety of different companies. How did Vick go from being one of the highest paid athletes to owing millions? The entourage didn’t help, especially since he was spending about $300,000 a month to support friends and family. But a bigger financial gaffe was entrusting his money to a woman who is now banned from working with any firm that trades on the NYSE because she bilked two old women out of $150,000, and a man who’s been accused of defrauding church members. His finances were such a mess that the bankruptcy judge appointed a trustee to help him out. But don’t feel sorry for Vick just yet – in an effort to pay down his debt, Vick will be selling three of his six homes.

Yachts? Six homes? That’s more luxurious than what most of us get to enjoy, but it’s nothing compared to the spending done by Mike Tyson. He might be the most well-known fighter of his generation, but if there was one thing Tyson was better at than boxing, it was spending money. In 2003, he filed for bankruptcy after his debt reached over $27 million, about half of which was to the IRS. What was he spending all his money on? For starters, two Bengal tigers for $140,000, for which he also had to pay a trainer $125,000 a year. But that was just a drop in the bucket. There was also the $4.5 million he spent on cars, and perhaps the most inane purchase of all, a bathtub for his first wife, Robin Givens, at a cost of $2 million.

While you may look to guys like these for guidance on which sneakers to wear or which car to drive, it’s probably best to leave the financial advising to tax pros, and not pro athletes.

The “top” five:

1.) Mike Tyson

Mike Tyson might be the most well known boxer of his generation (he’d probably hold that title outright if it weren’t for that George Foreman Grill). He earned at least $300 million in the ring throughout his career, but if there was one thing Tyson was better at than boxing, it was spending money.

In 2003, he filed for bankruptcy. His debt reached over $27 million, about half of which was to the IRS. Maybe he shouldn’t have bought the two Bengal tigers for $140,000, for which he also had to pay a trainer $125,000 a year. Although, that’s just a small drop in the bucket. He could’ve cut back on his motor vehicles, on which he spent about $4.5 million. But perhaps the most inane purchase? How about a bathtub for his first wife, Robin Givens, that cost $2 million dollars.

Tyson could’ve gotten his finances in order had he won the $100 million lawsuit against Don King (he was suing his former boxing promoter for cheating him out of millions in promotions), but the parties reached a settlement of $14 million, of which Tyson saw none. All of the money went to paying down his debt.

2.) Latrell Sprewell

Apparently Sprewell knew what he was talking about when he declined a three-year $21 million contract, and famously declared, “I have a family to feed.” That is, if you replace ‘family’ with ‘yacht’ and ‘feed’ to ‘pay off.' Maybe he was well aware that he needed a ridiculous payday to keep up with his lavish spending.

In August of 2007, a federal marshal seized his $1.5 million yacht after Sprewell had failed to pay his mortgage on the boat. The yacht, with the classy name, Milwaukee’s Best, was auctioned in early 2008.

Oh well, at least Sprewell would still have his home in River Hills, Wisconsin. That is, until it was foreclosed on in May of last year. So, let’s see, he lost his yacht and his house. It can’t get much worse. Oh, and now Wisconsin has filed a lawsuit for unpaid taxes. Hopefull Sprewell isn't expecting a big refund this year.

3.) Michael Vick

In 2006, Sports Illustrated estimated that Michael Vick made $25.4 million. Now, Vick owes well over $10 million to a variety of different companies. But don’t worry –- he has a plan. During his recent appearance before a bankruptcy judge, Vick stated he would pay back the money he owed by working construction.

Vick plans on donning a hard hat and punching the clock at $10 an hour. Let’s see: working 40 hours a week for $400, $20,800 a year…at that rate he could pay off the $10 million in…under 500 years! But his financial future all depends on his reinstatement into the NFL, and then a team willing to take a risk on him.

So, how did Vick go from one of the highest paid athletes to owing millions? To start, there’s the entourage. Vick was spending about $300,000 a month to support friends and family. But the biggest factor was who was in control of his money. Vick entrusted his money to a woman who is banned from working with any firm that trades on the NYSE because she bilked two old women out of $150K and a man who’s been accused of defrauding church members. His finances were such a mess that the bankruptcy judge appointed a trustee to help him out.

Vick owes over a million dollars in back taxes and it was recently discovered that he took funds from the pension plans of some of his employees. But if you are beginning to feel sorry for Vick, ("Then you’re not a dog lover"!) don’t. To pay off some of the debt, Vick will be selling three of his SIX homes. That’s less than one home per season. Do you really expect Vick to summer in Virginia? Do you?

4.)  O.J. Simpson

O.J. Simpson: acquitted of a double-murder in 1995; found guilty of wrongful deaths in civil court; wrote a book titled If I Did It; arrested in 2007 for a robbery that occurred in Las Vegas and was charged with, among other felonies, robbery with a deadly weapon, burglary with a firearm and assault with a deadly weapon; sentenced to at least nine years in prison (but as many as 33 years) for the incident in Las Vegas. Amazingly, he has financial troubles, too.

In 2007, the state of California released their Delinquent Taxpayers list. Guess who was on it. According to the record, Simpson owed $1,435,484.17 in personal income past due taxes, and a tax lien was filed in his case in 1999.

It should be noted that Simpson is not one of the delinquents included on the most recent list (but former Florida State running back Burt Reynolds is).

 

5.) Bjorn Borg

It’s a Bjorn Borg memorabilia sale! Everything he held dear must go!

In 2006, Bjorn Borg planned to sell his five trophies from his five consecutive Wimbledon championships, along with two of the rackets he won with, including the one he beat McEnroe with in 1980 in what most people consider the greatest match ever. The sale sparked an outcry from fans and fellow tennis players, and Borg decided to keep the trophies. Unfortunately, having already given them to the auction house, he had to buy them back. That wasn’t the first bad business decision Borg had made.

Borg’s company, Bjorn Borg Design Group, filed for bankruptcy in 1989 and Bjorn was forced to sell his house to pay off his debt. One of Borg’s problems was living in Sweden where they have a high tax rate. The Swedish government went after him for $40,000 in back taxes that he quickly paid off, but Borg learned his lesson and moved to tax-free Monaco.

6.)  Joe Lewis

Joe Louis is considered by many the greatest heavyweight boxer of all-time. He held the title for over 140 months, the longest stretch of anyone in boxing history. Unfortunately, the 'Brown Bomber' couldn't punch his way out of deep tax debt.

When Louis became successful, the top income tax level was 79%, and then during WWII, it rose as high as 90%. Louis donated money from two fight purses to the Navy Relief Fund and the Army Relief Fund, but those contributions were unable to be deducted, further complicating his tax problems.

After his initial retirement, Louis' debt forced him to attempt a comeback in 1950, but with a 90% tax rate, the comeback would not solve his financial woes. By the end of the '50s, Louis owed over $1 million in back taxes. In attempts to make money, Louis turned to professional wrestling and appearances on quiz shows. Finally, Louis even took a job greating tourists at Caesar's Palace in Las Vegas to try to pay down his debts.

7.)  Jack Clark

We're not what you'd call "car guys" here at RCS. So forgive us if we don't see the allure in owning a luxury automobile, let alone multiple cars. But we get it -- some people can't get enough. And when those people have money, they begin to stockpile a long list of expensive toys. One such person is Jack Clark.  

The four-time All-Star slugger had quite the fleet of automobiles (18 of them) when he filed for bankruptcy in 1992 while still a member of the Boston Red Sox.  

One story says Clark was once on his way to the ballpark for a game when he passed a car lot. Clark saw something he liked and dropped in to buy two sports cars for $90,000 each before continuing on to the game. At the time he filed for bankruptcy, Clark still owed money on 17 of his 18 automobiles; he had debts of over $11.4 million and assets of nearly $4.8 million.

8.) Travis Henry

Earlier this month, Travis Henry agreed to a plea deal stemming from his arrest last year for drug trafficking multiple kilograms of cocaine. Sadly, the venture into crime might have been a necessity, despite signing a 5-year, $22.5 million contract with the Broncos in 2007. 

One can point out the fact that Denver cut him just one-year into that deal (for which he received $6.7 million), but perhaps a bigger reason for his financial hardships was his family. Rather, his nine families. According to his lawyer, Henry “…doesn't have any money…the guy has significant financial issues."

The Prince of Procreation, who has nine kids with nine different mothers (all but one of the children were unplanned), is currently paying an estimated $170,000 in child support each year, and it’s left him broke.

“I’ve lost everything in this mess I’ve gotten myself into.”

9.) Evander Holyfield

If only Holyfield’s Real Deal Grill had done as well as the Foreman Grill, maybe he wouldn't be on this list.

In June of last year, it was reported that Holyfield’s $10 million mansion in a suburb of Atlanta would be auctioned off because he had defaulted on the loan he used to purchase the palace.

In a case of "kick him while he’s down," he was also being sued for falling behind on two months of child support, and a landscaping firm was demanding he pay over half a million dollars for services he had yet to pay. Eventually, Holyfield’s lawyers were able to stop the auction, and Holyfield kept his mansion. It’s a good thing, too, because otherwise they would’ve had to rename Evander Holyfield Highway, which sits just outside of his home.

In response to the firestorm from the media, Holyfield said, “I’m not broke. I’m just not liquid. I do feel kind of sad because things have always been positive and now everybody wants to jump on me like I'm the worst person in the world and I went out and blew all my money." So, things seem all fine and dandy for now. But with an electricity bill that reached $17,000 last December, stay tuned for more potential financial issues for Holyfield.

10.)  John Daly

There is no denying John Daly is one of the most intriguing characters in the world of golf. His anti-country club appearance and behavior have earned him a legion of fans. It has also cost him a considerable amount of money.

Daly has battled alcoholism for his entire career with at least three stints at the Betty Ford Clinic and recently, was fired by swing coach Butch Harmon, who said, "The most important thing in [Daly's] life is getting drunk." Daly's drinking and antics cause the PGA to suspend him for six months.

But his drinking is not the main source of his economic troubles, however; that comes from another vice, gambling, where he claims to have lost anywhere from $50 to $60 million. These debts have taken most of Daly's professional winnings, sponsorship money, and forced him into doing corporate appearances to make ends meet.

Just this past week, Daly was seen at The Masters, not playing (he's still on suspension), but selling John Daly merchandise, out of a bus.

Also not helping the finances: Daly has been married (and divorced) four times.