The 6 Most Undeserving Lottery Winners in History

There are people who win the lottery and immediately devise a stoic attitude, a wise investment plan, and a determination to remain the person they've always been. I would not be one of those people and, let's be honest, neither would you. Ours would be a millionaireship full of flipping the bird at plebeians as we board our golden, Bahama-bound Learjet. God, we would be the worst, wouldn't we?

Well, no. Our little kinks and haughty gestures would be downright pedestrian compared with the bullshit antics of some of the real lottery winners out there. The whole point of lotteries is that anyone can win, and sometimes the jackpot goes to the guy who can feel love only when he's watching documentaries of the Hindenburg disaster while huffing the ashes of cremated kittens.

Which is how we keep winding up with these fucking people in the news.

#5. The Winners Who Hid the Money from Their Spouses

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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.

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.

#4. The Group That Ruined an Entire State Lottery

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There are many ways to ruin a perfectly good game of chance. "Not winning" is definitely one. "Your opponent finally figuring out the rules" can be pretty nasty, too. And let's not forget the classic "The bullet's in the last chamber and it's your turn." I miss that one like a hole in my head. Still, the absolute worst party-pooper in any luck-based game is always math.

Franck Boston/Hemera/Getty Images
Counting is hard when you have an actual physical hole in your head, is what I'm saying.

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.

#3. The Man Who Kept $38 Million from His Friends

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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?

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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 ...

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