Last updated on

Look Who’s Screwed Up: The Unluckiest Lottery Winners You’ve Ever Heard of!

Lottery winners

Unlucky Lottery Winners – They Won to Lose

No truer words have ever been spoken (rapped?) about than those written by Notorious BIG in his song, Mo Money, Mo Problems.

I don’t know what, they want from me
It’s like the more money we come across
The more problems we see

Whenever we think of winning the lottery, we rarely ever consider of the problems that could come of it. We instantly think of how we can spend our cash. Sometimes we think of how we can make sure our money lasts us well into our later years or how we can make sure the winnings will take care of our families after we are gone. What we don’t think about are the people who come up out of the wood work looking for handouts. The sad truth is there are some very shady people out there and their true colors are revealed perfectly after winning the lottery.

The lottery can change people’s lives, both for the better and the worse. Unfortunately, these stories don’t have happy endings. Some of the protagonists end up broke, some have had family members turn against them and some have even lost their lives. Use these stories as cautionary tales when you play the lottery and know that things can always get screwed up.

Mark Gardiner – Betrayed by His Closest Ones

Mark Gardiner shared his story with the Daily Mail on May 2009. The Hastings man won half of £22.6 million and once people started to learn about the winnings, he got a rude awakening. His adoptive mother turned on him and sold a falsified story in order to cash in. Two weeks prior to winning the lotto, Mark’s mother said that he ”was no son of hers”. Mark then got unwanted press attention when someone who knew Paul, the other winner, phoned the media. The newspapers were plied with stories where Mark was being called a “lottery rat” and a “wife beater”. On top of that, when Mark and his then girlfriend, to-be wife, Brenda, went away for a week, the secretary of his glazing company called him and told Mark there was bags full of letters begging for handouts and marriage proposals. The friends he bought homes began to take advantage of him. In 2004, Mark and Brenda divorced because she couldn’t handle the pressure.

Mark Gardiner, lottery winner

William ‘Bud’ Post – Living on Food Stamps

William Post won the Pennsylvania lottery jackpot worth $16.2 million in 1988. The day that he won the lottery, he presumably had only $2.46 in his bank account. With such a large turnaround in financial status, Post spent his first of 26 annual lottery payments of $497,953 at a restaurant, a used car lot, and on the purchase of an airplane. He spent roughly $300,000. Not long after he won, he was sued by his landlady/girlfriend, Ann Karpik, for 1/3 of the winnings because the money that was used to purchase the ticket came from a ring that Karpik gave to Post to sell. After three years of legal battles, the judge ruled that Post was to give Karpik 1/3 of the winnings. By the time the ruling came in, Post was already in debt. In 1992, he refused to hand over the annual payment to comply with the judgment. This resulted in his lottery payments being frozen until the matter was settled. On top of the legal issues, there was a murder attempt targeting Post and his sixth wife. Post’s estranged brother hired a hitman to carry out the deed. Luckily, it was unsuccessful and the brother was arrested. Post eventually died in 2006. At the time of his death, he had racked up $1 million in debt and he was living on food stamps and a $450 a month stipend.

William ‘Bud’ Post, lottery winner

Jeffrey Dampier and Shakespeare’s Passions

The story of Jeffrey Dampier’s murder is the ultimate misfortune that lottery winnings could bring. In 1996, Dampier won the Illinois State Lottery to the tune of $20 million. He moved to Tampa, Florida and opened up a gourmet popcorn shop. He married a lady called Crystal Jackson. It wasn’t before long that Dampier began to have an affair with his sister-in-law, Victoria Jackson. The affair went on for seven years. Reports state that Dampier was taking care of Victoria and paying for an apartment that she was living in during the affair. It is also said that Victoria was abused by Dampier, who had “put himself in charge of every aspect of [her] life”. Victoria soon began to see someone else called Nathaniel Jackson and moved him into his apartment. The Jackson’s planned to rob Dampier because “the money wasn’t coming in fast enough”. When the pair abducted Dampier, Nathaniel ordered Victoria to shoot her former love. Otherwise, he threatened to shoot her. Victoria shot Dampier in the back of the head. She now serves three consecutive life sentences.

Jeffrey Dampier, lottery winner

Jack Whittaker: The Cursed Good Samaritan

The story of Jack Whittaker is a true story of good intentions gone wrong. In 2002, the businessman and devoted Christian won the biggest Powerball jackpot at the time – 315 million dollars. Just like any good Christian would do, Jack donated seven million dollars to the construction of churches, 10 percent of the sum to his parish and 100,000 dollars to the person that sold him the lucky ticket. It all seemed good at the time and many predicted that Jack be one of the people to escape the dreaded curse of the lottery millionaire. Little did these people know that Jack’s life was to get screwed up royally. Soon after news of his winning became public, Jack found himself being sued by numerous people. At one time the lawsuit count reached 460! As things went south, Jack began losing control. He was arrested multiple times for driving under the influence and he was also spotted multiple times at local casinos. It didn’t end there, however. Jack was robbed twice. One time he lost 545,000 dollars and the second time people took away 100,000 dollars from him. Unfortunately, Jack was to experience something even worse. He was planning on leaving all of his money to his granddaughter. The girl, however, became addicted to drugs and she was found dead before turning 18. Shortly after getting divorced, Jack also lost his only daughter.

Jack Whittaker