The 6 Most Undeserving Lottery Winners in History

Getting filthy rich overnight is fine and all, but what if you have a significant other? Uggh, am I right? That spoilsport might not agree with your wonderful plan of filling a swimming pool with strippers and crack cocaine and dive-bombing in for the rest of your glorious (though likely short) life. Hell, they might even assume you're, hah, sharing with them.

If that seems like a dickish line of thinking, Arnim Ramdass is about to prove you right. When the universe decided to compensate his unfortunate name by providing him and his lottery posse with sufficient means to ram all the ass, he knew exactly what he would do with his $600,000 share: hide that huge, heavily publicized pile of money from his wife by any means necessary. It was time for Bullshit Feedin' Olympics, and Ramdass was both the reigning champion and the only competitor.

Via Teinteresa.es
He had already been practicing on their wedding cake.

Ramdass did actually manage to smoke-and-mirrors his wife for a period of time. Beyond that, the story is delightfully Rashomon. Some sources say the wife found out the truth when idly Googling her husband one day. Others indicate Ramdass bought a new house behind her back, and she found a congratulatory card from the real estate agency in the mail. My personal favorite is the Fox News version, where ol' Ramdass decided to go full sitcom, attempting to hide his heavy media presence with a never-ending stream of excuses to keep the television turned off, and randomly disconnecting their phone, because stealth personified, that man. What most sources do agree on is the fact that when he was confronted, he did the classy thing and ran the hell away, leaving no traces of himself or his money save for (probably) a man-shaped hole in the wall. His wife was left facing an eviction and a pile of bills that he had neglected to pay.

Meanwhile, Denise Rossi became the second most surprised member of her family when she won a cool $1.3 million in the California state lottery. The most surprised? Her husband, whom she immediately and without explanation divorced as hard as she humanly could. Of course, she conveniently forgot to mention her winnings to either her husband or the divorce court. This "total asshole" stratagem for money management proved to be a viable one, and Rossi waltzed away scot-free ...

lisafx/iStock/Getty Images
... wait for it ...

... for about 1.5 years, after which karma decided to deliver a slam-dunk in the form of postal incompetence. Rossi's ex-husband accidentally received a wrongly stamped letter that revealed her wealth to him. Of course, he took that shit to court, where the judge awarded every single cent of Rossi's lottery money to her ex-man.

Oh, and the best thing? If she had bothered to mention the money during the divorce, she'd probably been allowed to keep it all since, you know, it was her winning ticket to start with.

In the 2000s, the state of Massachusetts found this out the hard way when an entire state lottery was thoroughly reamed by a math-savvy gang of MIT students. The game in question was called Cash WinFall, and it insisted on doing things differently from most state lotteries: The jackpot never rose above $2 million, and if no one won it was rolled down into a number of smaller prizes. The MIT gang quickly figured out that during the roll-down phase, each lottery ticket was technically more valuable than what they actually cost, so by buying enough of them you were bound to make a profit. One of the students tested this by purchasing $1,000 worth of tickets ... and raked in a cool $3,000 of winnings.

Now, that was not a dick move -- it was just math. (They're hard to tell apart, believe me, I know.) The dick move was when they decided to make a business out of their discovery. Realizing they could rake in massive profit if they bought tons and tons of lottery tickets, the students pooled their money and started hassling store employees around the state by purchasing thousands of $2 lottery tickets.

Harry Todd/Hulton Archive/Getty Images
"Yeah, that should be enough. Mind if I pay in change?"

Before long, the lottery officials smelled something strange, namely the overheating elbow grease of exasperated cashiers punching in a hundred thousand tickets all over the state. Realizing shenanigans were taking place, the lottery runners stood up, steadied themselves ... and did absolutely nothing, because, "Hey, high-stakes rollers be feedin' money to our system, sweet!"

So the MIT guys (and a couple of other scientist groups) kept it up for years, their bastardry becoming so lucrative over time that they managed to not only quit their day jobs but attract actual investors to their scheme. By the time officials decided that enough was enough, the students had milked the system to the tune of over $8 million.

Shockingly, Cash WinFall is not around anymore.

Here's the good news: You've won $38.5 million in a lottery! Woo! However, there's a downside: It's one of those pesky tickets where everyone at work has chipped in. Boooooo.

The thing is, you'd very much like to keep all that money yourself. But you're a tad worried your straight-and-narrow, goody-goody co-workers (some of whom, it occurs to you, are pretty large and short-tempered) would see it as, hah, dishonest. What to do?

conejota/iStock/Getty Images
What to doooooo?

If you're Americo Lopes, you won't waste any time mucking about such moral dilemmas. You cash in the ticket, quit work due to a fictional foot surgery, and keep on living just like you always have, except super rich, which is neat. It's a perfect crime, really. The only way you could ever be found out is if one of the other guys -- each of whom is a close friend of yours, by the way -- ever gets suspicious and, say, checks the public list of winners for the lottery that your little group has played for years. But why would anyone ever do that? It would take some really peculiar circumstances, like if the guy who's holding the ticket suddenly bails out of work and starts behaving like he had recently acquired a lot of money ...

... oh, right.

When Lopes was found out and promptly sued, he immediately realized the error of his ways. So he embraced his friends, gave them their due share of the winnings, and proclaimed he had learned the most valuable lesson of them all: You can't put a price tag on friendship.

Via The New York Times
"Now let's all hold hands and walk into the sunset, ha ha."

Or the exact opposite. Lopes went down kicking and screaming, maintaining throughout the proceedings that it was in fact he who was being robbed by the other guys. Even after he inevitably lost the case, he kept to his story, proving once and for all that dishonest money can at least buy you big brass balls.

Still, Lopes' antics were child's play compared with those of ...

Bigbee was like any other Florida resident -- just looking to live her remaining years in the warm, alligator-infested climate of America's Dong. There were only two things setting her apart from her peers: winning the lottery and dabbling in human trafficking.

When Bigbee won a cool $1 million in the Missouri Powerball, she immediately made it her mission to buy all the shit ever: a place in Florida, a car, cool things for family and friends, and, of course, some really awesome stuff for her cat (because everyone knows cats will cut a bitch if they don't get their share). Sadly, a million is only sufficient to buy a moderately impressive amount of shit, a fiscal fact that Bigbee realized two years later as the floor beneath her money pile finally started to show. This created a considerable problem: She wasn't happy with returning to a more modest lifestyle, but she didn't have the means to continue her current one.

What she did have, however, was an 8-week-old grandson. So she did the logical thing and attempted to sell him to a stranger. For $75,000. That she was willing to haggle down to $30,000.

FamVeld/iStock/Getty Images
"We also offer some very attractive installment plans."

How ... how does that even work? Are baby markets a thing in Florida? Can any random schmuck just wander into a seemingly abandoned parking lot with a spare baby and a dozen black cars will emerge with their drivers waving wads of cash and going, "Psst"? Please never answer that question.

Luckily, one of Bigbee's daughters (not the mother of the kid -- she was totally participating in the plan) called bullshit on mom's Kid-o-Mart aspirations and alerted the authorities. Bigbee and her boyfriend were arrested before the transaction could take place, and the saddest real-life imitation of an Elmore Leonard novel this side of North Korea finally ground to a halt.

Remember the beginning of this article, where I offered a seemingly off-handed quip about a swimming pool full of strippers and crack? That wasn't a throwaway line -- it was a brick prologue to the story of Michael Carroll, quite possibly the most gleefully, gloriously horrible lottery winner to ever grace the Earth with his million-dollar bling and private demolition derby fields.

Carroll was a petty criminal that stumbled upon winning a British lottery jackpot in 2002. A 19-year-old advocate of the British "chav" culture (basically, white trash with some hip-hop aesthetics thrown in), he was the kind of guy who you automatically assume is wearing a court-ordered electronic tag. This might seem a tad elitist, if it wasn't for the fact that he celebrated his victory while wearing a court-ordered electronic tag.

Via MSN Money
The champagne says "poise and class." Everything else says "those bubbles are not coming from the Jacuzzi."

The British yellow press immediately recognized Carroll's worth as potential tabloid fodder, dubbing him The Lotto Lout and gleefully throwing fuel in the money bonfire that the kid would surely become. He didn't disappoint: What followed can accurately be described as Animal House with an all-Belushi cast. In the span of eight years, Carroll blew his entire $15 million fortune on a massive, nonstop binge of prostitutes, drugs, neighborhood-wrecking parties, and constant petty and not-so-petty criminal behavior, all fueled by a $3,300 bag of crack and a couple of bottles of vodka. Per day.

Eventually, things got so bad that the officials in Carroll's hometown were forced to set up an actual Michael Carroll Damage Hotline, a 911 lite solely devoted to reports of his trail of destruction. Yep, notoriously unfazeable British authorities basically classified the man as a natural disaster.

Via the Sun
An asteroid, possibly.

Somehow, Carroll survived his eight solid years of debauchery. His money and entourage, however, are long gone. These days, Carroll is a 30-year-old, somber man who knows full well his ass has been thrown right back to square one. He's supporting himself with odd jobs and insisting that he's happy to live the quiet life again (although that doesn't stop him from continuing to play the lottery).

And with that, we conclude our story. Because it's customary for articles like this to end with a valuable life lesson, here's one from Mr. Carroll himself:

"When you give nine million pounds to a 19-year-old, what do you think is going to happen?"

Now we know, Mr. Carroll. Thank you for taking one for the team, I guess?

Pauli Poisuo is a Cracked columnist, freelance editor, and only vaguely aware of the concept of money. Follow him on Twitter.

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