11 Worst Lottery Winner Horror Stories: Problems With Winning The Lottery

When you think about winning the lottery, quite presumably the last thing you would think about would be anything like these 11 worst lottery winner horror stories: problems with winning the lottery. That’s right—lottery winner horror stories! Most would be inclined to muster up ideas that would be comparable to the stories found on another one of our recent lists of the 5 Most Successful Lottery Winners and Their Good Stories. While many may fantasize about how their lives would change for the better if they could just hit the jackpot, most folks don’t take into consideration that there can be real problems with winning the lottery. You may or may not have noticed, but we are introducing 11 lottery horror stories and previously, only presented 5 success stories. Now, why do you think this is? The answer is simple! More often than not do the problems with winning the lottery outnumber what good some winners can actually get out of it.

One common mistake many lottery winners tend to make time and time again is that they opt for a lump sum payment instead of the annuity checks. Both options do have their pros and cons, however, most lucky lottery winners have never even seen such large amounts of money—let alone, had the opportunity to manage it. They squander away their winnings with nothing to fall back on and are often left in a worse position than they were before they hit it big, selling their belongings and even filing for bankruptcy from all the debt they have accumulated. Not that those who take the annual payments end up any better. A lot of times you will find that they’re spending money they don’t physically have, yet and their checks are spent before they even arrive!

Along with greed, developing bad habits from leading such a luxurious life, being harassed and a target for thieves, some more unlucky lottery winners journey down an even more formidable road to ruins as a result of winning the lottery. Perhaps we should start calling them “lottery losers” because some go through some serious losses including loss of a spouse through a divorce and in a worst case scenario, many have even lost their lives!  One thing’s for sure, you’ll hear a little bit of it all in the 11 worst lottery winner horror stories: problems with winning the lottery.

 

11. Thomas & Denise Rossi

Not going to lie, this first horror story on our list of worst lottery winner horror stories, brought smiles to some of our faces. A story of irony and some dumb broad who got what she deserved! A bit harsh? You be the judges!

Denise Rossi was married to Thomas Rossi for 25 years. According to Thomas, they had a happy and healthy relationship, doing everything together including even sharing the same toothbrush! You can imagine his surprise when Denise had him served with divorce papers while he was at work. Not only was he shocked, but couldn’t understand why she was in such a hurry to have their divorce finalized. Little did he know, she had won $1,336,000 in the California State Lottery just 11 days prior.

Fast forward about two years after the divorce. Thomas’ life and finances were falling apart while Denise had done everything she could to keep her annual installments of $66,800 a secret. She even went so far as to direct the checks to her mother’s house so that he would never find out. But karma was about to catch up to her as Thomas accidentally received a letter for Denise from a company trying to buy her annuity checks in exchange for a lump sum.

Upon piecing together his ex-wife’s deceitful and downright sheisty acts, Thomas was quick to take her back to court and fight for half of her winnings. He was, after all, entitled to it! But much to both Thomas and Denise’s surprise, because of her dishonesty the judge decided to award Thomas with ALL of the winnings! That’s right! Every. Last. Penny! The kicker? The whole reason why Denise was so unhappy in their previous relationship to begin with, was because he was always broke. Now he has everything, and she was left with nothing. Ain’t that about a bitch!

 

10. David Lee Edwards

What happens when a convicted felon is awarded $27 million in lottery winnings? Well, we’re about to tell you the story number 10 on our list of worst lottery winner horror stories!

Much like many lottery winners, David intended for his winnings to not only last him for the rest of his life but provide for his daughter and future generations, as well.  Upon winning the Kentucky Powerball in 2001 he was quick to spend it on multiple cars, houses, and a medieval armor and weapons collection (all of which were reproductions that weren’t really worth anything) among other things. He intended on using his winnings responsibly, but in fact did just the opposite. After only one year of winning the lottery, he had blown through roughly $12 million dollars!

Aside from acquiring useless items such as his $1.9 million jet, $78,000 gold watch, $159,000 ring and a $30,000 plasma screen TV he also contracted hepatitis from repeated drug use. By 2006 all of his money was gone! He didn’t even have so much as a life insurance policy to leave to his daughter.  Now that he was broke, his wife (who had also developed hepatitis) left him. With nothing left he was forced to sell all of his belongings and ended up living in a storage unit surrounded by his own feces. In the end, he died alone and penniless just 12 short years after winning all that cash. No wonder this one is on our list of worst lottery winner horror stories, right?

 

9. William Post III

Why there isn’t already a movie or book about William “Bud” Post, beats us! The story number 9 on our list of worst lottery winner horror stories starts with an orphan who would grow up to be an unsuccessful man. With less than $2.50 in his bank account, Bud pawned off a ring and gave the $40 he got for it to his landlady—with which he was pretty well acquainted (bow-chicka-wow-wow!)—in exchange for an equal amount in lottery tickets. Among those tickets would be one that would turn the indigent man’s life around. That ticket was worth $16.2 million!

And boy, oh BOY did that ticket change his life! It took his already troublesome existence and turned it upside down! Within three months of receiving his first annual installment of just under $498,000, he had accumulated $500,000 in debt. His irresponsible spending spiraled out of control from there and led him back to where he started on disability only receiving $450 a month.

But that’s not all! Aside from losing it all, he was arrested for shooting at his sixth ex-wife AND a bill collector, the landlady who got him the tickets sued him for half of his winnings [and won], and to top it all off—his own brother hires a hitman to try to kill him!

The movie would have everything from the unfortunate character who gets lucky, to the woman (or women!—the dude did end up with six failed marriages and one successful one), and even a bit of action! The only thing one of the worst lottery winner horror stories is missing is a “happy ending”.

8. Gerald Muswagon

We are continuing our list of worst lottery winner horror stories with the story number 8 – this Canadian man got lucky and won $10 million (about 7.5 million US dollars) off of a $2 Super 7 ticket. While his family thought that this was his big break, he managed to spend every last cent of the money in a short amount of time.

Making one bad decision after another, Gerald blew the money on cars and was known to hand out big screen TVs to his friends left and right. He even bought a house for the sole purpose of partying in. He would throw nightly parties with an abundance of drugs and alcohol. With what he had left after spending so much on useless crap and parties he tried to open up his own lumber business that turned out to just hemorrhage even more of his money.

After getting a taste of the high-life, Gerald’s poor spending habits would leave him flat broke and forced to get back to work in order to support his wife and family. At his wit’s end, he was later found at the end of a rope in his parent’s garage.

 

7. Jack Whittaker

Whatever it was that prompted Andrew Jackson Whittaker, an already wealthy man, to try his luck at the lottery turned out to be one of the worst ideas of his life which ranks 7th on our list of worst lottery winner horror stories! Jack was the prosperous owner of a construction company when he hit the Powerball for $315 million. Worth millions already, he donated about 10% of his money to charities including his own Jack Whittaker Foundation. He was even nice enough to reward the convenient store clerk who sold him his winning ticket with a house, new vehicle and $50,000 cash!

So, where did he go wrong? With all that money his bad habits began to consume him, spending large amounts of money at strip clubs on a regular basis. He was robbed on multiple occasions while at these clubs, and some of the strippers who knew of his wealth even plotted to steal from him, as well (as if he wasn’t already handing over enough of his money to them).

But that’s not the worst of it! His granddaughter, who he loved dearly developed a drug problem that would not only cost her her life, but the life of a boyfriend whom she negatively influenced, also. Jack truly believes that if it weren’t for the money he had won, that she and her young lover would still be alive. You see, after cashing in, he began handing over $2,000 a week to his granddaughter in hopes that the money would help her. Instead, he was feeding her drug habit and only adding fuel to the fire.

While his granddaughter’s death was a direct cause of his big win, his wife and daughter died a few short years thereafter, and Jack was convinced that his winning ticket was actually a curse.

 

6. Michael Linskey

This just so happens to be one of our favorite of the 11 worst lottery winner horror stories (#11 being the obvious fave, as the only person who got hurt deserved what she got!). Not because it has a happy ending—we’ve already established all these stories end badly—but because at least one of the men tied to the story has a pretty well-known reputation. You may even recognize the South Boston mobster played by Jack Nicholson in the movie The Departed who went by the name of Whitey Bulger. Not the kinda guy you wanna mess with—that’s for sure!

You can imagine how Michael Linksey felt back in ’91 when he purchased a Mass Millions lottery ticket from a liquor store controlled by none other than Whitey Bulger, himself. When it was found out that the ticket was worth $14.3 million, it didn’t take long for Whitey to pay his new, rich friend a personal visit. Basically, Michael had one of two choices: Split the money with the feared mob boss, or die! Obviously, he split the money 50/50, but it couldn’t have been easy to just hand over millions of dollars that he had won fair and square.

 

5. Ibi Roncaioli

Despite the $5 million that Ibi won playing the lottery, her death didn’t seem fishy in the slightest bit. Her and her husband, Joseph, had been married for 30 years, and he was already making a respectable living of over $200,000 a year as a gynecologist. The money she had won was just the icing on the cake.

Already in control of the couple’s finances, Ibi began to frivolously spend the cash she had won, and—before she knew it—all the money was gone! Shortly thereafter, she was found dead on the couch. Since she already had a bit of an alcohol and pill-popping problem, her death was assumed to be linked to one of those causes. However, when the autopsy came back that despite her addictions her major organs were all in good shape, experts started to dig a little deeper. They found track marks all over her legs and feet and questioned her husband as he had access to medical supplies. He admitted that he had been running tests on her, and gave her some pain medication, but his story just didn’t seem to add up, and he was charged with manslaughter. It is believed that her irresponsible spending drove her husband to end it once and for all. It didn’t help that their own son confessed in court that they had a rocky marriage, and didn’t even share the same bed at night. And now, let’s see the top 4 on our list of worst lottery winner horror stories.

 

4. Billie Bob Harrell Jr.

Much like many, Billie Bob Harrell Jr., the number 4 on our list of worst lottery winner horror stories, was struggling to make ends meat before he hit the Texas Lotto Jackpot for $31 million. And like many who win such large amounts of money, he began to attract the unwanted attention of complete strangers asking for handouts.

While Billie was pretty generous with his winnings—donating large sums to churches and charities, and even nearly 500 turkeys which he donated to the poor—the attention began to get the better of him. Trying to lead a normal life, he was forced to change his number repeatedly. Yet people would still call.

Less than one year after his win, he and his wife separated. Although it is not certain why she left, it may have been that it was the only way she could think of to escape all that unwanted harassment. This only made Billie even more miserable. Only two years after he had cashed in, his son found him dead with a self-inflicted gunshot wound. Shortly before his death, he had claimed that winning the lottery was the worst thing that had ever happened to him.

 

3. Jeffrey Dampier

The details of Jeffrey Dampier’s death following his Illinois state lottery win of 20 million big ones actually made it on an episode of ‘Killer Couples’, a show that airs on Oxygen. It’s quite fitting because the story behind his murder is much like a movie you would find on Lifetime.

His stroke of luck should have been the end of his troublesome life, but instead brought it to an end and unveiled a slew of family secrets along the way. Aside from opening his own gourmet popcorn business, he began to shower his mistress, who was also his sister-in-law, with expensive gifts. His mistress, Victoria, was also cheating on her boyfriend with Jeffrey who ranks 3rd on our list of worst lottery winner horror stories. Unable to explain her costly new items, she had to come clean to her boyfriend. Enraged, he plotted to kill Jeffrey and forced Victoria to do the dirty work.

With a gun pointed at him, Jeffrey begged for his life and offered to give the angry couple whatever they wanted. Of course, they wanted his money, but revenge may have played a small role, as well. Victoria’s boyfriend ordered her to shoot Jeffrey and threatened that it was his life, or hers. Technically speaking, her life ended, too that day, for she is now facing life in prison.

 

2. Urooj Khan

You ever hear the Alanis Morissette song… You know the one that goes, “he won the lottery and died the next day”? Pretty much the same thing happened to Urooj Khan after he won a million dollar jackpot. Only, this was no accident!

Apparently, upon winning his wife decided to cook him a celebratory meal. Some lamb, a little bit of curry, and oh!—don’t forget the cyanide! At first, officials claimed that it was an unfortunate natural death. But his brother had his suspicions. He insisted Urooj had a proper autopsy (which would be ignored until his wife quickly tried to cash in his check). They had found traces of cyanide in his system! To think, his wife must have been one greedy woman to want all that money to herself. And now, let’s see the number one on our list of worst lottery winner horror stories.

 

1. Abraham Shakespear

Although many unlucky lottery winners ended up losing their lives after cashing in, Abraham Shakespear happens to be the worst of the worst lottery winner horror stories. His unduly kind-hearted nature and generosity only make his case that much more terrifying. It was actually most likely because of how giving he was that he ended up buried under a slab of concrete.

Unable to say ‘no’ Abraham was known to hand out money left and right. He would lend money that would never be repaid, give large sums to those in need and he even opened up the doors to his $1 million home to complete strangers who needed a place to stay for the night. His charitableness attracted the attention of Dorice “Dee Dee” Moore, who he befriended and trusted enough to let her manage his finances after she offered to ‘help’ him regulate what he had left.

Long story short, Abraham went missing, and his new friend would tell his friends and family members that he went on vacation or was just trying to get away for a little while. Abraham’s best friend and former employer, Greg (who Abe had lent about $60,000 to), became suspicious of this Dee Dee, and when police labeled him a suspect in Abe’s case, he agreed to help them find out the real story. He felt it was the least he could do to repay the friend who had lent him money and got him out of a hard time. You could say that he set Dee Dee up, but her own stupidity got the best of her. She sent text messages from Abraham’s phone to Greg and other family members. Now, that doesn’t seem all that suspicious, but little did she know Abraham was illiterate and her text messages only sent red flags to everyone who actually knew him.

Although Greg never got Dee Dee to confess, he got more than enough evidence to pin the death of his beloved best friend on her, including the burial site (which was located on her property, by the way) AND murder weapon! Yet she STILL claims she’s innocent! But justice was served, nonetheless. Dee Dee now faces life in prison, and the remaining lottery winnings she had killed him for was divvied up amongst his children. What gets us is that he was such a sweetie—he probably would have just given Dee Dee the money, had she just asked him for it!