On Christmas morning in 2002, Jack Whittaker woke up to perhaps the biggest gift imaginable. Whittaker had won the Powerball lottery jackpot -- a whopping $315 million.
"I got sick at my stomach, and I just was [at] a loss for words and advice," Whittaker said. "You know, I was really searching for advice, and it's, like, Christmas Day."
It was a made-for-TV Christmas story, and Whittaker's hardworking family became celebrities overnight. Whittaker's wife, Jewel, and their granddaughter Brandi Bragg would appear on no fewer than eight television shows. But as Whittaker celebrated his good fortune, he had no way of knowing that he was embarking on a journey that would lead to tragedy and the loss of everything he held dear.
Whittaker now says that he regrets winning the lottery.
"Since I won the lottery, I think there is no control for greed," he said. "I think if you have something, there's always someone else that wants it. I wish I'd torn that ticket up."
Whittaker had the very best of intentions: He truly wanted to share his good fortune and help people.
"I wanted to build churches," he said. "I wanted to get people food that didn't have food. I wanted to provide clothing for children that needed clothing."
Within months, Whittaker was making good on his promise. He handed over $15 million for the construction of two churches alone.
The initial blitz of publicity meant that everyone knew about Whittaker's record-breaking win, and he was besieged by requests for help. In order to deal with these requests, he formed the Jack Whittaker Foundation. Jill, the clerk who sold him his winning ticket, went to work for him in the mailroom.
"There were so many letters that they wouldn't even deliver the mail. It was nothing for us to sit for 10 hours just opening envelopes," said Jill, who asked that her last name be kept private.
Jill says the foundation received all kinds of requests, such as, "people wanting new carpet, people wanting entertainment systems, people wanting Hummers, people wanting houses -- just absolutely bizarre things."
Whittaker gave away at least $50 million worth of houses, cars and cash. Suddenly, the man who won a fortune at Christmas had become everybody's Santa Claus.
"Any place that I would go they would come up," he said. "I mean, we went to a ballgame, a basketball game … and we must have had 150 people come up to us … and it would be going right back to asking for money."
For a man who didn't start out with much, the experience was a bit overwhelming. "I grew up very, very poor in Jumping Branch, W.Va.," said Whittaker. "We never had a lot of luxuries. We never had a car. We didn't have a TV until later in life."
At the age of 14, Whittaker met the woman who would become his wife, and started his own construction company. Whittaker said it was the birth of his granddaughter that finally changed his obsession with work.
"I was with my daughter going to her doctor's visits," he said. "And Brandi waved at me on the first sonogram, so I was hooked then."
By the time Whittaker won the lottery, he said, he was doing $16 million to $17 million worth of work. He enjoyed years of success with few complaints, but less than a year after winning the lottery things began to change.
Rob Dunlap, one of Whittaker's many attorneys, said Whittaker has spent at least $3 million dollars fending off lawsuits.