Jul 25, 2026
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Add us on GoogleJack Whittaker thought he had gotten the best present ever from Santa when he woke up on Christmas morning in 2002 and realized he had won the Powerball jackpot, which totaled $315 million.
But five years later, he told ABC, “I wish I’d torn that ticket up.” He died of natural causes in 2020.
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Whittaker’s tale is not rare. However, it is a stark warning about the trappings and hazards of a sudden influx of wealth — something that many families will face in the coming years as part of the great wealth transfer, where boomers will leave anywhere from $36 trillion to more than $100 trillion to their heirs.
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As for Whittaker’s sudden wealth, he tried to do good with it and share it, since he grew up poor. In the end, though, he ended up alienating some people, losing others, along with most things he held dear.
Celebrating the win
The immediate period after the lottery win was a good one for Whittaker. He donated $15 million for the construction of two churches and set up the Jack Whittaker Foundation to focus on the tsunami of requests he got from strangers for help, hiring the clerk who sold him his winning ticket to help go through the voluminous mail.
Ultimately, he gave away over $50 million worth of houses, cars, cash and more. And he was known for driving around his hometown in a Lamborghini throwing cash out of the window.
But within a year, things took a bad turn.
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Lawsuits and tragedy
While the lottery win brought Whittaker a tremendous influx of wealth, he wasn’t exactly hurting before he won. His startup had turned into a thriving construction business before he bought the ticket and he was already worth $17 million.
Within a year of his win, he and his company were inundated by a flood of lawsuits. Whittaker would spend millions defending himself. Those lawsuits impugned the reputation of the company he had worked hard to build and Whittaker began drinking heavily.
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“I just got to the point that I just couldn’t tolerate what was happening to me anymore,” he told ABC News. “I would fly off the handle and if somebody wanted to fight me, I’d fight them. I just didn’t care.”
Two years after his victory, his granddaughter, to whom he reportedly gave $2,000 per week, was found dead of a drug overdose. Later he would bounce a check for $1.5 million to Caesars Atlantic City, which was meant to cover gambling debts.
In 2008, his wife of 42 years filed for divorce, which led to a prolonged legal battle. And in 2016, his house burned to the ground.
“Since I won the lottery, I think there is no control for greed,” he said in 2007. “I think if you have something, there’s always someone else that wants it.”
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Chris Morris is a veteran journalist with more than 35 years of experience at many of the internet's biggest news outlets. In addition to his activities as a writer, reporter and editor, Chris is also a frequent panel moderator and speaker at major conferences, including CES and South by Southwest.
