He won $315 million in Powerball. He said it was the worst thing that ever happened to him

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.

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.

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.