And #1 is...

#1 – MC Hammer

MC Hammer has had the hammer come down on him in judgements against him several times now, after earning hundreds of millions in his career. Unfortunately he managed to spend it all even faster, and joined the ranks of the many rappers who have went broke.

When you grow up with less than nothing, quickly earn $33 million from a hit album in the 1990’s while you’re still in your early 20’s, blow your fortune on not one, but TWO private helicopters for you and your posse, it’s not surprising that you can spend that fortune so fast!

Though that was all nearly 30 years ago, Hammer seems to still not have hired an accountant to manage his money as in 2011 it was reported he owed nearly $800,000 in back taxes to the IRS.

#2 – Jordan Belfort

The man portrayed in the 2013 smash hit movie the “Wolf of Wall Street” by Leonardo DiCaprio, Jordan Belfort earned more money in a year than 99% of people will ever see in their entire lives, seeing an amazing annual income of over $250 million in his early 20’s.

Compared to Allen Stanford’s 110 year prison sentence, Mr. Belfort got off easy with only a 2 year prison term, and a forfeiture of every single dollar, and piece of property he had in his name. He’s still hundreds of millions of dollars in debt as a result of a court decision, but is slowing trying to repay that by doing “inspirational” speaking tours.

#3 – Allen Stanford

At one point Stanford was considered a genius and was worth $2 billion. The SEC started to wonder where Stanford was getting all of this money from, and it turns out he wasn’t just a genius, he was also a big time con-man that was taking people for a lot of money.

You could say that Allen Stanford’s fall from grace was rather abrupt. Where most people just lose their fortune, Mr. Stanford is currently behind bars in a Federal penitentiary serving a 110 year sentence for defrauding investors out of more than $7 billion! The gig was up when the company eventually went belly-up and investigators determined he spent the bulk of the money on his over the top lavish lifestyle, with mansions, penthouses, and private jets. In addition to the lengthy prison term, he was also ordered to pay a fine amounting to nearly $13 billion!

#4 – Sean Quinn

Formerly the richest man in all of Ireland, Sean Quinn managed the rare feat of going from a net worth of $6.5 billion to being nearly $4 billion in debt, almost overnight.

In an unfortunately poorly timed move, Mr. Quinn invested 25% of his family’s entire wealth in an Irish bank, just before the 2008 Financial Crisis. This wouldn’t have been so bad if he didn’t leverage his family’s insurance company to make the investment, resulting in both companies, and his entire empire collapsing in billions of debt.

To help offset some of his newly found poverty, Quinn tried the age old art of asset stripping. Quinn knew that it was illegal, but took the chance anyway. This led to Quinn being sent to jail by the Irish High Court, but only for nine weeks, so it wasn’t a terrible idea if you really think about it. Quinn now has to find a way to rebuild his fortune with five children in tow.

#5 – George Foreman

Before flipping burgers on TV earned him a $250 million fortune, the legendary boxer wasn’t just broke, he was on the verge of total bankruptcy. Though he was an Olympic gold medalist from the ’68 Olympics held in Mexico City, and involved in some of the greatest boxing matches of all time, including against legends such as Muhammad Ali, he squandered his entire fortune by the age of 45. Fortunately his luck changed for the better when Hulk Hogan did not answer his phone in time. It led to George Foreman being offered that famous grill that you’ll find in every kitchen in North America!

#6 – Willie Nelson

Willie Nelson is one of the most recognizable names in both the country music industry and the list of most popular stoners ever. Seriously, Nelson is right up there with Snoop Dogg himself.

Nelson has also been the recipient of many awards, including eleven from the Grammys and seven from the American Music Awards. As one of the most decorated artists ever, it’s surprising that he ever went broke. There was a time when Willie Nelson wasn’t just broke, he was nearly $17 million in the hole to the worst people to owe, the IRS! Unfortunately Willie trusted the wrong people to manage his fortune, and in 1990, the country music allstar had all of his properties and bank accounts seized by the IRS to pay towards his debt. Nelson was also forced to produce two new albums, with 100% of the profits from each going directly to the IRS to pay off the rest of what he owed them.

#7 – Bjorgolfur Gudmundsson

Former Icelandic billionaire Bjorgolfur Gudmundsson (try saying THAT 3x fast!) was worth a cool $1.1 billion before the markets annihilated him and his son Thor (seriously) during the credit crisis.

There was also the small issue of his suspected heavy involvement in a fraud and embezzlement scheme, but on paper, and without account for any Swiss bank accounts, Mr. Gudmundsson is legally broke. As is the case with most embezzlement trials, there were multiple counts. While most of these cases have around 10 or 20 counts, Gudmundsson was held trial on a whopping 450 counts, yet only had to serve 12 months in prison.
The good news for Gudmundsson was that second chances exist, and he was able to rebuild his fortune after making the move to Russia. The bad news was that Iceland wanted the money back that he made and now his net worth has been squashed all the way down to $0. That’s right, you are currently richer than a guy that used to be a billionaire.

#8 – Johnny Unitas

A legendary former NFL quarterback, Johnny Unitas was one of the highest paid players in the entire league during his career that began with the Colts in 1956.

His salary in 1973 had grown to $250,000 (equivalent to $1.3 million in 2014 dollars) with a signing bonus of $175,000 (another nearly $1 million in 2014 dollars) on top of that. Through a series of horribly bad luck, each and every single one of the businesses (half a dozen industries) that he invested in all failed and he was forced to file for bankruptcy in 1991. That doesn’t hold back the fact that Unitas was one of the greatest of all-time, and his bankruptcy didn’t disrupt his post-playing career too much. Unitas still made money through appearances, signings and TV gigs that got him by until his death in 2002.

#9 – Scott Eyre

Scott Eyre was one of those left-handed relief pitchers that made his way around the Major Leagues for years as someone who was supposed to put out the fire. Unfortunately, Eyre couldn’t put out the fire on his finances.

Eyre played for the White Sox, Blue Jays, Giants, Cubs and Phillies before his career ended after 12 solid seasons. What happened with all of his money afterwards is probably the most surprising thing he’s done (besides sign a deal with the Cubs). Professional athletes are particularly susceptible to being taken advantage of, losing their millions on scams and bad investments brought to them by friends and family. Scott earned over $17 million in his career up until 2009, but reportedly was left with only $13 in his savings account after being scammed by Allen Stanford in his infamous scheme that cost investors billions of dollars.

#10 – Kim Dotcom

At the height of his success Kim Dotcom was worth a staggering $200 million. But, like an ironic scene from one of the movies pirated on MegaUpload’s servers around the world, his entire net worth vanished in the blink of an eye as part of an over-the-top and theatrical Hollywood style raid on his New Zealand compound, thought to be the most expensive private home in the entire country. While the courts have spent the last couple of years deciding just how liable Kim Schmitz is (if at all) for some of the $500+ million in damages being sought against him, his money is currently in lockdown, along with all of his worldly possessions.