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.
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