History's 6 Greatest Examples of Financial Fail

We live in uncertain economic times. In moments like this, sensible folks save money, invest wisely, and stock up on ammunition for the forthcoming class wars.

Others, however, dump their savings into a gold-plated wheelbarrow so they can carry the $50,000 required to buy a loaf of bread in style. Today, we celebrate those fiscal morons that make lists like this possible.

#6. Mike Tyson

How badass of a boxer was Mike Tyson? He knocked unconscious 26 of the first 28 opponents he faced, 16 of them in the first freaking round. Most of his opponents had no trouble meeting a qualifying weight prior to their fight because of the regularity with which they shit themselves beforehand.

He was the undisputed champ by age 21. Realizing that Tyson was running out of people to punch in the real world, Nintendo inserted him digitally into Mike Tyson's Punchout!! so he could haunt the dreams of children and future opponents alike.

Despite a couple of hiccups along the way, Mike Tyson's notoriety allowed him to eventually command over $30 million a fight, building a fortune in excess of $300 million.

So What Happened?

Well, the "hiccups" included an embarrassing loss to 42:1 underdog Buster Douglas and a rape conviction in 1992. As hiccups go, those would cause your metaphorical diaphragm to eject your lungs on to the pavement. He was incarcerated for 3 years, only to return to boxing more unhinged than he left it:

Still, his $300 million had to make him feel better about all that. After all, that's more money than you can ever spend!

Actually, no. Especially if, like Tyson, you paid hundreds of thousands of dollars to a gentleman answering to "Crocodile," whose job it was to shout "Guerrilla Warfare!" at pre-fight press-conferences. Or if you purchase two Bengal tigers that cost $12,000 monthly for care and feeding (Bengal tigers will apparently only eat meat that has been first coated in gold).

According to reports, Tyson had:

"...custom-made Harley Davidsons, a fleet of Rolls, Bentleys and Ferraris. Once, in Vegas, he bought a batch of six Rolls and distributed them among his friends. He's had a half-million dollar watch emblazoned with pornography."

But worst of all, Tyson got wrapped up in a very expensive addiction. That's right: pigeons. Tyson started a pigeon-breeding operation, winding up with 350 world-class birds imported from all over the world, costing thousands a month in care and feeding and four elaborate coups to house them on his property.

In 2003, Tyson declared bankruptcy, owing approximately $10.2 million to the IRS and creditors.

"Why did I do this?"

What We Can Learn from This:

In the event you become the heavyweight boxing champion, fight the urge to purchase a $100,000 platinum bracelet inscribed with "Heavyweight Champ." We have found that the gold belt occupying a third of your torso does an equally good job of advertising the same. Not to mention the inscription severely limits the potential pool of people to resell to.

#5. Thomas Jefferson

On top of Thomas Jefferson being one of the great icons of American history, he also had the distinction of being the president with the worst credit rating ever.

Jefferson inherited an estate of about 2,500 acres and 30 slaves from his deceased father. It's hard to demonstrate what that would be worth in modern terms, especially since pesky human rights nutjobs have prevented us from determining present market value on slaves, but it's probably a lot.

Of course the man wasn't exactly sitting on his wealth, he made the modern equivalent of $307,000 a year as President, for eight straight years, plus all the perks you can make on the side (such as signing autographs at car shows or whatever).

We can pretend he's signing an autograph, but that's probably the Constitution or whatever.

So What Happened?

We could point out that during his term he spent the equivalent of $120,000 on wine alone. He once ordered 382 bottles in a single month.

But that doesn't seem unreasonable. Being president is a stressful job, you need to kick back now and then with a case of wine.

Then, we have Monticello. This was a time when houses got big and elaborate enough, you gave them names. Single names, like Cher and Prince.

That's the tool shed.

The sprawling estate took nearly 40 years to construct. It was 43 rooms and 11,000 square feet of awesome.

He had little wine elevators built into the walls, to shoot bottles directly up from the wine cellar to the dining room. The man could sit there and eat, reach out to the wall and a fucking bottle of wine would pop into his hand. Bottle's empty, just drop it down the chute, and a full one takes its place. Sure, there was a slave down in the basement operating it, but still. The man knew how to live.

He also these Scooby-Doo style hidden revolving shelves installed, which the slaves would use to serve food, sparing the guests the unpleasant experience of seeing a slave. Are you picturing this? They put food on one side, spin it around. The man had his whole operation set up so that the finest food and drink in the world just magically appeared out of his walls.

Hey, did we mention the house had its own beer cellar? Where he could brew his own, to the tune of 200 gallons a year? Does Bill Gates even fucking have one of those?

Also, it's on a mountain.

Jefferson had his kitchen utensils shipped in from France, in an era when shipping things to the other side of the planet wasn't exactly easy. All told he had 86 crates of paintings and decorations and every other thing boated in from there.

The man couldn't have been more of a pimp if he had outfitted his farm equipment with 20" spinnaz.

But as you can guess, it didn't come cheap. Debts ran out of control and despite the evident strength of his pimp hand, his debtors' payments were infrequent and inadequate. It was really only his prominence and reputation that kept the bill collectors at bay, at least until he died. The executor of Jefferson's estate was left with the modern equivalent of $1 to 2 million in debt, and most of the estate was sold off to pay it off.

What We Can Learn from This:

If you're having difficulty paying back a mounting debt, consider declaring independence from a sovereign nation to forge ideals from the French Enlightenment period. It's a long shot, but TJ demonstrated the power of a killer rep.

#4. Kim Basinger

Remember her? She used to be the biggest female star in Hollywood. Kim Basinger's rise proved that the American dream is attainable for anyone that happens to be a balls-hot, skinny white chick.

Basinger was a beauty queen who was plucked out of her first national competition by the Ford Modeling Agency. When she wasn't busy commanding $1,000 a day for various shoots and shunning sustenance, she studied acting. Her move to Los Angeles lead to appearing as James Bond's love dumpster du jour, Domino Petachi, in Never Say Never Again.

God Almighty, he's hairy.

Shortly thereafter she starred her in seminal work (pun strongly intended) 9 1/2 Weeks, an erotic thriller that famously caused both Siskel and Ebert to state it gave them visible erections. Ultimately it was her last minute replacement of Sean Young in 1989's Batman that cemented her super-star status and really brought in the big bucks. What could possibly go wrong?

So What Happened?

Her starpower was certainly sturdy enough to weather any financial storm as long as she didn't make any really, really ludicrous financial decisions like trying to purchase an entire town or something.

Oh shit.

Yes, based on the advice of her family members, many of them likely albino cousins named Jed, Basinger purchased Braselton, Georgia for $20 million. She had designs on turning it into a tourist attraction or possibly just wanted to boost the box office of her films by subjugating the captive population to see each one several hundred times.

Shockingly, the town of 1,206 people didn't become the new Las Vegas.

Then, she got nailed with an $8 million breach of contract penalty for backing out of the film Boxing Helena, at which point Basinger filed bankruptcy.

Just look at that sweet, filthy bankruptcy. Hell yeah.

What We Can Learn from This:

Look, it's going to come up at some point. The salesman will have a great pitch, you'll be impressed by the tour, but damnit, people, don't buy a fucking town.

Now we could add that you shouldn't back out of movies at the last moment or you might get sued, but it turned out Boxing Helena was a movie about a woman who has all of her limbs amputated and lives in a box. So that one was probably worth the bankruptcy in the long run.

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