April 6, 2007 — -- 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.
"I've had over 400 legal claims made on me or one of my companies since I've won the lottery, " said Whittaker.
When asked why that might happen, Whittaker said it's because "everybody wants something for nothing."
As his company's reputation was challenged by lawsuits, Whittaker began drinking heavily to console himself. At night, he made the rounds of the local bars throwing money around everywhere he went.
"I just got to the point that I just couldn't tolerate what was happening to me anymore," he said. "I would fly off the handle and if somebody wanted to fight me, I'd fight them. I just didn't care."
Whittaker alienated just about everyone in town, and things came to a head when he left his car running in front of the Pink Pony strip club and more than $2,000 in cash was stolen.
"I parked my car in the middle of the driveway, I went in to get me a drink to go, and I was drugged and my briefcase was stolen," Whittaker said.
The money was recovered, but the luckiest man in West Virginia was left friendless and lonely. It seemed as if everyone still wanted a piece of his winnings, but the one person Whittaker was determined to share every moment of his good fortune with was his granddaughter.
"What I really enjoyed the most was … watching Brandi enjoy it," he said.
Whittaker bought and decorated an elaborate home for Bragg and her mother that included a perfect recreation of the bottle from the 1960's TV sitcom "I Dream of Jeannie." He also gave Brandi about $2,000 a week and bought her four new cars. Whittaker said while Bragg was only 17 years old at the time, she was very responsible with her money.
"To a young kid cars mean a lot," Whittaker said. "She had four cars and I'm very proud that she had four cars."
According to her friends, Bragg's cars and cash began to attract the attention of some "bad people," including drug dealers.
Whittaker said, "She was bitter because she had lost some of her friends, I mean the drug dealers, just ganged up on her because of me."
Bragg started to use illegal drugs. Whittaker repeatedly tried to get her help and sent her to several treatment programs, but she couldn't stay clean.
"She doesn't want to be in charge of the money; she doesn't want to inherit the money; she just looks for her next drugs," Whittaker said. "She said, 'Pawpaw, all I care about is drugs.' It broke my heart."
Bragg's friend Jessie Tribble was a drug user too. In September 2003, Tribble was found dead of a drug overdose in a house owned by Whittaker. Tribble's father believes that his son might be alive today if he hadn't had access to Bragg and her weekly allowance.
"I'm going to say this with total conviction. I blame her for my son's death. I hold her accountable," he said.
Whittaker doesn't feel responsible for Tribble's death.
"The house was closed down," he said. "They didn't have permission to be in my house."
Almost two years after Whittaker hit the jackpot, Bragg disappeared. After a frantic two-week search, on Dec. 20, 2004, she was found dead, wrapped in a plastic sheet, dumped behind a junked van. The cause of death was listed as unknown. Whittaker believes that the Powerball win had become a curse upon his family.
"My granddaughter is dead because of the money," he said.
"She was the shining star of my life, and she was what it was all about for me," he said. "From the day she was born, it was all about providing, and protecting, and taking care of her. You know, my wife had said she wished that she had torn the ticket up. Well, I wish that we had torn the ticket up too."
Whittaker believes that money isn't what makes people happy -- family is.
"Family is what is dear," he said. "I don't know where it'll end. But you know, I just don't like Jack Whittaker. I don't like the hard heart I've got. I don't like what I've become."