30 Lottery Winner Stories (That Don’t Always Have Happy Endings)



Winning the lottery might sound like the best thing that could ever happen to you — but that is not always the case. There are lottery winner stories that will make you jealous and others that will make you happy you’ve had to work hard for your money.

Lottery Winner Stories — 20 People On Reddit Share Their Experiences

Winning the lottery is not always a blessing. Sometimes it causes tension within families. Sometimes it leads to a lifetime of debt. Here are a few lottery winner stories that have happy endings — and some others that didn’t turn out so well. 

1. Everyone begged for her money: A lady who worked at the same company as me won just under $100 Million. They said the number of sob story letters and requests for money was simply unbelievable, even a year later. People claiming to be veterans, or asking for them to pay for surgeries, and more. They simply stopped opening their own mail. I don’t know if that’s something I could handle, but dang. Funny part of her story, she still went to work for about 3 days before realizing that she didn’t need to work anymore, and quit. Her husband and her both had worked at that company for about 25-30 years.

2. She went broke within three years: A friend of a friend won a $17m jackpot back in the mid-1990’s. Within 3 years, she was completely broke. Her family still hounds her for money constantly and refuses to believe she doesn’t have any. She couldn’t say “no” to her family, they bled her dry, and now that she hasn’t got anything left to give, they won’t speak to her because they think she’s holding out on them.

3. She sued the lottery company for selling her a ticket: There was a person who won the EuroMillions £1m raffle and became stressed from suddenly having a large sum of money and had her relationships with her friends were affected. Despite not going broke, she claims to have felt meaningless with her wealth. She decided to sue Camelot (the company that runs lottery games in the UK) for negligence in providing good advise to someone at her age (17 at the time) and also claimed that it was irresponsible to allow under 18 years olds to buy lottery tickets.

4. He lost his closest friends: My grandfather won 30,000 in Australia in 1977, not long after lotto was introduced. It bought him a truck to run his own business and a house in a nice suburb which he and my grandmother lived in until they passed away. It also brought out people looking for handouts which ultimately drove my grandfather away from close friends and turned him in to a reclusive semi alcoholic.

5. He was already rich before the lottery win: A person I knew won one of the first lottery’s in Florida he won 7 million before taxes it did not change him, he was already rich, (money goes to money) he won another big jackpot a few years later.

6. They are in even more debt now: Ex girlfriend’s aunt and uncle have won three times. Odds say that if you are within two degrees of knowing someone who won it, your chances are pretty beat. These guys won three times. 1$ million, $50k, $1.2 million. All in the span of four or five years. Bought a brand new Suburban, Mercedes and Dodge ram. Remodel the house, finish the basement, do a lot of nice work. Didn’t pay off any debts, didn’t pay off their house or cars. They are currently in more debt than they were before the lottery. People can be stupid.

7. He wasted all the money: I know a guy. He’s an Indian and won a lottery with a prize money of $700,000. He was a poor guy who did a day job. We were all happy for the guy. But few years later, we heard that the guy lost all of the money and is now back into doing day jobs. Lessons learnt: You won’t value anything if you earn it for free.

8. He couldn’t claim the money: My dad won $5000 recently but couldn’t claim it due to being in debt. So he gave me the ticket and had me cash it in for him. He gave me $1000, not bad for a quick trip to the lottery office. My life isn’t much different now, I’m broke till payday.

9. He finally followed his dreams: I knew an attorney that won a Publisher’s Clearinghouse for 10 million, probably 20 years ago. He resigned his associate position and opened his own office doing law that interested him, not law that necessarily paid the bills or padded the pockets of the partners. Good for him.

10. The money completely ruined his life: I met a guy who won over 5 million. I worked in a courthouse at the time and was in the courtroom when he entered his guilty plea for possession of drugs and guns. As I recall, he got a 10 year mandatory minimum sentence. He said that winning the lottery ruined his life.

11. He opened a bed and breakfast: The Bed and Breakfast my husband and I like going to is owned by a guy who won the lottery. The B&B is open randomly, you literally cannot book more than two weeks ahead of your visit, in case he’s traveling. He travels a lot. His house is basically a museum. He seems to particularly enjoy traveling to nomadic regions. The first time we stayed there, we were trying to figure out what he does for a living, then we saw a small frame by the door, and in it was a copy of his winning lotto ticket. I don’t remember how much he won, but he’s made it work.

12. They started smoking cocaine: I had an uncle who won and his whole family got really into cocaine and now they are broke as expected.

13. He kept his exact same job: There was a guy in the town I grew up in who won around £3-4 million. He bought a nice house for his family and some new cars, I’m sure he’s done other things with the money but those I know for certain. The best part? He his still doing the same job as he was doing before, which was being our local postman. Sometimes in the winter he will deliver the mail in his shiny new Audi Q7

14. She wasted her money on cars: A former neighbor won one million dollars three, maybe four years ago by getting the five white balls on Powerball. She took the lump sum and ended up with roughly $550,000 after taxes and fees. She promptly started buying cars and giving people money like she had won $550 million and not $550,000. She didn’t get a new roof or siding on her house like she needed to. About 10 months into it the cars were gone and replaced with a 5 year old Honda. The roof and siding still needed repaired. Thankfully she sold and the new owners really fixed the house up.

15. They traveled the world: My parents won the Readers Digest sweepstakes about 20 years ago ($5 million over 30 years, so about $160,000 a year). It’s been wonderful for them. They were both teachers, so they were able to retire in their 50s, pay off their house and our college debts, travel all over the world, come visit us frequently (particularly after we produced a grandchild), buy a house in the town where they grew up for their retirement, and generally live a good, quiet life in their old age. They’ve helped us out around the edges, too, but generally the money hasn’t caused any family problems–it’s been an absolute blessing.

16. He gave the money to charity: My dad won $15,000 and got back about $10K. we had recently bought our first house, already paid in full, so he just bought really nice hand stitched lather sofas. cost: about $6000. the rest, he gave to charity.

17. They put a downpayment on a house: A couple I know won about $60,000 after taxes. They put a downpayment on a house, and that’s it, no toys, not even a fancy night out. It couldn’t have happened to people who deserve it more, imo.

18. They gave the money to their kids: My friends parents won about $100k, they (entire family) went on a month long vacation, bought a boat (they’re really into sailing) and saved the rest for the kids. Nothing special, and nothing audacious.

19. He used the money to help others: My friend Earl won 100K on a scratch off ticket. He decided that he was going to try and help out the people that he’d hurt in his past.

20. She retired early: A lady I worked with won $1,000,000 on a $20 scratch ticket. The most common question I heard around the office was “Who drops $20 on a scratcher?” Great deal for her. She was all set to retire in a year or two so she just took off a bit early and bought a new car.

21. He quit his job and then got a new one: An ex-coworker of mine won 24,000. He immediately quit his job and came back for another one a week later. He obviously didn’t get his old job back.

22. He moved to another state: My friends uncle won about 40 million in the lottery around 5 years ago. He had no hesitation to move to Florida (we live in Canada), and rarely has contact with the family.

23. They never claimed the money: Someone in the next town over won $80,000 last February, and they still haven’t claimed it. There’s only a couple weeks left to collect the money… I hope they’re just waiting till the last week to do so.

24. The family sued each other: The Lavigueur family is a Quebec family who made headlines in Canada in the 1980s after winning a lottery jackpot of $7,650,267 in 1986, then the largest prize ever given by Loto-Québec. The trials and troubles of the Lavigueur family have since become entrenched in Quebec popular culture for various reasons: the fact that a poor family became multimillionaires overnight; the intervention of a stranger who found the lottery ticket lost by the family’s father; the judicial saga of one of the family’s daughters, the only member of the family to not have participated in the purchase of the winning ticket, suing her father for a fraction of the jackpot; the subsequent family disputes that tore apart the family which dissipated its fortune, all of which received wide coverage in the mainstream media of Quebec.

25. They saved their money for their futures: My parents won a million dollars a few weeks ago. They haven’t received it yet, but they’re going to give each kid about 20k, get officially married, and put the rest in a high yield savings account. When they’re ready to retire in a few years, they’ll buy a little house in upstate New York and live off of the interest and social security.

26. He started his own business: My dad won $250k Australian dollars 4 years ago, he left his job and started his own business with it as starting capital, has around $1.8mill in assets now.

27. He quit his job because of harassment: A high school teacher of my younger siblings had won (about a year after my two siblings who are twins had already graduated). He won 21 million Canadian, didn’t know he had a winning ticket for something like 4 months and found out after he got back from a trip to Asia or something. Had to leave his job teaching (which he loved) because students and fellow teachers were harassing him for money. The school faculty apparently got upset because after he won, he only gave the entire staff $100 gift cards to Starbucks and felt they were entitled to more.

28. He spent the money on his family: My dad won 40,000 in the lottery. He sent half to Jamaica and the other half was split among other different things. The money went super fast and I really don’t think anyone who got a piece bought anything meaningful.

29. He drank himself to death: My father won a big lottery in the 1960s, quit his job and drank himself to death in a couple of years. Only the best scotch would do, a bottle a day…

30. We took a trip to Hawaii: My family won $10,000 from the lottery. We used it to go on a pretty awesome trip to Hawaii. TC mark



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