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Every week, millions of people across the globe shell out handfuls of their hard-earned cash to take a chance at winning enough money to make all of their problems go away. Yeah, about that ...

See, it turns out that a sudden influx of cash actually doesn't make all of your personal demons vanish as if by magic. And in many cases, it makes things much, much worse.

5
Michael Linskey Wins Lottery, Winds Up on the Wrong Side of the Mob

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In the summer of 1991, Michael Linskey purchased a Mass Millions lottery ticket from the South Boston Liquor Mart and found out a few days later that he had hit the numbers in a big way. With no other winners that week, it meant that Linskey would be in possession of approximately $14 million. Boom! Life was about to become one big vacation, baby!

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Finally, time for that diamond-encrusted condom.

Just one minor problem: The liquor store was owned by a Southie mobster by the name of Whitey Bulger. You may have heard of him. To understand how utterly screwed Linskey found himself, it's important to know that Bulger was nothing like your normal run-of-the-mill gangster. In fact, Jack Nicholson played a slightly less batshit crazy version of the man in The Departed. So when Bulger found out that somebody won $14 million from his liquor store, he decided to pay the lucky winner a visit.

It is unclear what happened at this meeting, but afterward Linskey came forward and basically said "No, no, it was just a misunderstanding. I wasn't the sole winner -- Whitey and I bought the ticket together with two other mob goons, uh, I mean, good friends of mine. That's a thing that could happen, right?"


What are a few shotguns waved in faces between lotto buddies?

Later on, court documents would reveal that Bulger did turn over about 700 grand up front in exchange for $7 million in annuities. It was a good deal, relatively speaking, when you consider that Linskey got to keep breathing.

As for Bulger, as of 2013 he's on trial for mobster crimes such as murder, money laundering, extortion, and other evil guy stuff. But, um, you didn't hear that from us.

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We've never even heard of whatshisname, the guy we were just writing about.

4
Man Wins $75,000, Blows Up His House

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So picture this: It's the middle of February, and you're in Wichita, Kansas. No, you didn't lose a bet with a wizard or anything -- you actually live there of your own volition.

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And once you get past that big-ass field of grass, you'll find ... another big-ass field of grass!

In February of 2013, a 27-year-old Wichita resident and employee at a local Sonic burger stand stopped on his way home, picked up a scratch ticket, and hit it to the tune of 75 large. The young man had just enough time to show up at the lottery office to receive his cash, plus a free Kansas Lottery T-shirt, which he abruptly changed into before going out and buying several ounces of weed and methamphetamine. Later on, while hilariously still wearing his lucky lotto winner T-shirt, he decided to reload a butane lighter while standing right next to a gas stove.

It is unclear whether or not the young man had a basic understanding of how pilot lights work, or if he was just blazed out of his mind at the time. Anyway, you get the picture. The pilot spark managed to ignite flames from the butane canister, and, well ...

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Happy New Year! And happy new shrapnel wounds.

The guy survived, fortunately. Firefighters and cops were called to what was left of the house, and in keeping with Murphy's Law, while the ensuing conflagration tore the unfortunate house a pretty good one, it also managed to leave enough drugs intact for the lottery-winning genius to be placed under arrest as soon as he got out of the hospital. Hey, at least he had money to cover the bill!

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3
Amanda Clayton Wins a Million Dollars, Gets Arrested for Welfare Fraud

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As a contestant on the Michigan Lottery-sponsored game show Make Me Rich! Amanda Clayton hit it big and walked away with the million-dollar grand prize on September 11, 2011. Maybe that should have been taken as an ominous portent or something, but whatever. So what could possibly go wrong this time?

Amanda Clayton / Facebook
The most difficult trial in her life now is cashing that giant check.

Well, for starters, Clayton was receiving a couple hundred dollars each month in state assistance at the time of her big win, and then after she received the giant cardboard check (on live television, no less), the state continued to put money on her card.

For, like, a year.

Clayton didn't really see the problem with this. As she put it, "I still need the money, now I've got two houses to pay for."

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Because juries are so sympathetic to snarky rich people.

The state of Michigan disagreed and charged her with two felony counts of welfare fraud with a penalty of up to five years in prison for each count. Complicating matters was a second charge leveled at her by one of her neighbors after an altercation over where a bag of grass clippings should be dumped. And by altercation, we mean Clayton allegedly sent a couple of goons to her neighbor's house to sort things out with "a knife, baseball bat, and pellet gun."

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And a backhoe. Don't ask why.

Clayton responded to this rapidly expanding list of woes by dying promptly of an apparent drug overdose a year after her big win. Holy shit, that one got dark toward the end there. Hey, maybe this next one won't be so bad ...

2
Jose Antonio Cua-Toc Wins $750,000, Gets Kicked out of the U.S.

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In early 2000, Jose Antonio Cua-Toc fled from Guatemala to the U.S., where he found gainful employment in Macon, Georgia, and began his search for the American dream. In November of 2010, he finally found it, or at least that particular American dream some folks aspire to vis-a-vis being randomly handed $750,000.

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Wait, that isn't the only type of American dream?

At the time of the lottery win, Cua-Toc was working as a laborer for a guy named Erick Cervantes. Having crossed the border illegally, Cua-Toc was not a U.S. citizen, and he didn't have a visa, either. His quite understandable concern was that he might face some unwanted scrutiny by cashing in the winning ticket.

So Cua-Toc went to the one guy he knew might be able to help him out -- his boss. And Cervantes basically said, "Sure, I'll cash it in for you." You know what happened next, don't you? We don't have an exact transcript of the conversation, but the gist of it likely went something like this:

Cua-Toc: "Were you able to cash in that ticket for me?"

Cervantes: "Ticket? Why, I have no idea what you are talking about, stranger." (Speeds off on a brand new gold-plated jet ski while laughing maniacally.)

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"Sorry, I can't hear you over the sound of all this yachting."

So Cua-Toc kinda flipped out a bit after that, and the next few years weren't too fun. He allegedly threatened Cervantes and his family and was jailed for several months on terrorism charges. He then became embroiled in a very costly lawsuit to try to recoup his money.

Cua-Toc eventually did win much of his money back in the lawsuit, since there is no law preventing non-U.S. citizens from playing the lottery, any more than a tourist from outside the U.S. would be prevented from collecting his winnings from a casino poker tournament. However, after receiving what was left of his prize ($500,000 after taxes, minus $250,000 in attorney's fees, minus an additional $50,000 in fines, and so on), Cua-Toc was given a choice: leave the country voluntarily or be deported, in which case he would be barred from returning to the U.S. for a period of at least 10 years. Oh, and then he was thrown in jail on a drunk driving conviction.

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On the plus side, he now had enough money for Martha Stewart prison.

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1
Timothy Elliott Violates His Parole by Winning a Million Dollars

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Timothy Elliott's life ambition was to win one of the grand prizes in the Massachusetts state lottery. We're not saying that to be snarky -- this actually did seem to be Elliott's grand vision for his life. For example, there was the time in 2006 when he committed armed robbery at one convenience store, fled to another convenience store, and spent his take on lottery tickets (and didn't win).

We should point out here that Elliott was diagnosed with schizoid personality disorder, and for the above incident he was given probation and mandatory mental health counseling in lieu of any real jail time for his caper. And, as part of his probation, he was instructed to stay out of trouble: no leaving the state, no drug use, no gambling, the standard stuff.

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Nothing but sitting in a chair all day long, super depressed.

But then his luck took a turn for the better when he purchased another state lotto ticket the legit way in November 2007 and won a million bucks. Finally! See, persistence pays off, kids.

Oh, wait -- remember the list of stuff he was supposed to avoid while on probation? And how "gambling" was on there? Yeah, as it turns out, paying a dollar or whatever for a scratch ticket is still considered gambling, if you want to get technical about it. So when Elliott cashed in his $1 million winning ticket, a picture of him went in the papers. Somebody saw the (actually pretty awesome) photo ...

Massachusetts State Lottery
That's a mug shot we wouldn't be ashamed of.

... and realized that it was none other than that Timothy Elliott. He was arraigned less than 48 hours after his big day, facing not only a return to jail, but also the forfeiture of his million-dollar dream.

Fortunately, this story has a relatively happy ending. Elliott is still an ex-con, but the courts overturned the probation violation and ended up giving him his winnings, with the provision that he pay a modest restitution. We say "relatively" happy ending, because if you have learned nothing else from this article, it's that winning that much cash appears to be a goddamned curse.


Will Millar would like to thank his parents, Charlie and Ellen, for giving him the inspiration for this article. He'd also love it if you checked out his book, Infernal Machines.

Related Reading: People have actually gotten super rich through methods even less effective than the lottery. One chef for Google made $26 million when the company went public. If you do manage to wind up wealthy, these luxury spa treatments are a great way to waste your new-found wealth. Why WOULDN'T you pay to be massaged by snakes? Now that you're really enjoying the fruits of your fantastic fortune, take a minute to learn the things you need to stop saying.

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