5 Sad Winning Lottery Stories To Make Powerball Losers Feel Better

You’re probably feeling a little down right now because the lottery ticket you’ve ripped to shreds and set on fire didn’t contain any of the winning numbers…or they did and you’re trying to find a way to tape the smoldering ashes back together.

Don’t fret, my friend. The chances weren’t in your favor in the first place. The odds of winning the grand prize stood at 1 in 175,223,510, according to the Multi-State Lottery Association. Besides, money doesn’t automatically equal happiness. Some of the biggest lottery winners of all time were plagued by mankind’s greed and suffered huge financial losses, endless legal battles with friends and family members, death and (worst of all) a visit from the IRS.

So if you’re one of the 175,223,510 statistical people who didn’t win the Powerball jackpot, you can always take solace in the misery of those who did and lost it all. If you did win, I’d like to speak to you about an investment opportunity that you won’t want to miss.

1. Jack Whittaker


This West Virginian won $315 million in the Powerball lottery and was so moved by his family’s supreme luck that he vowed to use the money for good. Unfortunately, every other human being on the planet smelled an opportunity and pounced on the poor guy until his wallet started coughing up blood.

He began getting tons of letters asking for donations or investments for projects and “charitable” causes such as new entertainment centers and Hummers. The mail deluge was so large that he had to form a foundation and hire a staff just to go through it all. He also started his own construction company that saw some years of success but as soon as some of his clients learned he was a million dollar winner, they slapped him with a lawsuit that ended up costing more than $3 million in legal fees for over 400 claims. The fact that he had to give the money to lawyers is sad enough, but the story gets worse from here.

Whittaker turned to booze to ease the pain of constantly being asked for money. He ran out of friends and pretty soon, his granddaughter’s drug habit attracted some people who didn’t ask for money as politely as most total strangers. She eventually turned up dead herself in an abandoned van. Whittaker said in an interview with ABC’s “20/20” that he wished he and his wife “had torn the ticket up.”

2. Jeffrey Dampier


This Florida lottery winner spread his new-found fortune to the people who he loved most: his family. And how did they pay him back? One of them hatched a scheme to kidnap and kill him so she could get her greedy paws on the rest of his money. Would you expect anything less from an in-law?

Dampier won $20 million in the Illinois Lotto and spent a good portion of his winnings on his extensive family. His nine brothers and sisters all got free houses and cars. He took 38 members of his family on a very lavish, week-long Caribbean cruise as a Christmas present. And somehow, his sister-in-law and her boyfriend who had also gotten a free apartment out of the deal actually thought to themselves that he wasn’t being generous enough.

She and her boyfriend lured Dampier into their apartment, tied him up with his shoelaces and kidnapped him at gunpoint. They loaded him into a van and shot him point blank in the back of his head. Both received life sentences.

3. William Post III


If you’re anything like me (first of all, you have my deepest sympathy and I urge you to seek counseling immediately), you probably have a long “To Do” list in your head for when you win the lottery. You’ve probably imagined buying a house so big that it makes Mitt Romney’s summer home look like his butlers’ quarters. You’ve got tickets to Las Vegas and a four class presidential suite filled with champagne and strippers already booked in your mind. Hell, you’ve probably even thought about using the money to buy an elephant because… why the hell not?

No matter what your lottery dreams have cooked up, they pale in comparison to how this Pennsylvania lottery winner actually spent his winnings. He took home a huge check for $16.2 million at a time in his life when he literally had $2.46 to his name. So he did what any normal human being in that situation would do: he spent a buttload of money. The first two weeks after he won saw purchases for a restaurant, a used-car business, a huge mansion and a twin-engine plane, which was a gutsy purchase for a guy who doesn’t know how to fly a plane.

Three months later, he found himself in the red to the tune of $500,000. His brother tried to hire someone to have him killed. A lawsuit from his former landlady and ex-wife ordered him to pay a third of his initial winnings after she claimed he agreed to split it with her. Since he couldn’t pay, the court ordered the lottery commission to freeze his payments. After a massive liquidation of his assets and a prison term for assaulting a debt collection agent, he spent his final days living off disability payments of $450 a month.

4. Dionie Reyes


Even if you’re not smart enough to recognize that your most grounded spending fantasies won’t work in reality, you can still avoid learning a very hard lesson about crushing financial debt and math by turning to this Philippine money typhoon.

Reyes hit the jackpot in 2008 by winning more than 14 million pesos in the nation’s 6/42 lotto draw, an amount that roughly translates to around $300,000. He wasted no time putting the money to good personal and charitable uses such as a 4 million peso home with a gas guzzling SUV in the driveway and large donations to his close family and friends. He also “donated” a lot of money to casinos, bars and hookers.

Reyes ran through his entire lump sum in three months, spending all 14 million pesos on everything his heart and other parts of his anatomy desired. He also came out of the three month money binge with 500,000 pesos of debt hanging over his head. He was so broke at the end of his hooker and tequila shopping spree that he had to take a charitable donation to get lifesaving heart surgery. The worst part is that he doesn’t regret the money he wasted on himself, even though he has an 11-year-old adopted son. That’s going to be an awkward Fathers’ Day. What do you get for the man who has everything… and then gives it all away to bartenders and prostitutes?

5. Evelyn Adams


Of course, no defeat or loss is more crushing than the one that happens the second time around. The first one was full of mistakes and pitfalls that you couldn’t have seen coming but the second one hurts more because you often make the same mistakes you thought you learned the first time. I can’t imagine how many times it would take for this lottery winner to win and lose everything all over again before she takes a hint or maybe I just don’t want to imagine it.

This New Jersey native actually hit the state’s lottery jackpot twice in 1985 and 1986. Her extremely good luck netted her $5.4 million in winnings and somehow, she took every dollar bill she was given and not only flushed it down the toilet but saw that it was backing up and decided to “jiggle the handle.”

Her winnings are now floating somewhere through the labyrinth of bank accounts and change counters in Atlantic City’s network of casinos. She didn’t lose it by making a massive, million dollar bet. What she didn’t spend on gambling went to a lot of her “friends” who didn’t stop asking her for handouts because they knew she wouldn’t say no. She also whittled away a big part of her fortune just by playing slot machines in practically every casino in the city. She spent the rest of her days living in a trailer unless she tried to pawn it and convert the money into nickels for another run at the casinos.



    1. bobbyd3 says:

      Dampier's story sounds like a Denzel Washington movie in the making.

    2. Jeremy Johnson says:

      Very well-written and entertaining article!

      1. Laszlo says:

        The money will never stay with those who don't have the proper mindset…
        Usually lotto /casino winners are not those peoples…
        They had the luck but they were "not ready" for it…
        And as this story shows money also surface the real nature of many "friends and family"…

        Sad story…

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