Two years later, the picture the public is seeing now is a mug shot of a haggard, somber Whittaker.
Whittaker, 57, has been arrested twice for drunken driving in the past year and has been ordered to go into rehab by Jan. 2 for a 28-day stay. He also faces charges he attacked a bar manager, and is accused in two lawsuits of making trouble at a nightclub and a racetrack.
"That's probably the unfortunate situation of maybe having too much money, too much time on his hands," said Steve Zubrzycki, who works for a company that started selling "Where's Jack?" T-shirts after authorities issued an arrest warrant for Whittaker earlier this month.
Although he was already a wealthy contractor, Whittaker became an instant celebrity on Christmas Day 2002 after winning a $314.9 million Powerball jackpot. He took his winnings in a lump sum of $113 million after taxes, and at a news conference in which he came across as a jolly saint, he promised to donate one-tenth to his church and contribute to other causes.
He soon created a charity to help people find jobs, buy food or get an education; he split $7 million among three churches; and he gave money to improve a Little League park and buy playground equipment and coloring books for children.
But in August 2003, a briefcase containing $545,000 in cash and cashier's checks was stolen from Whittaker's sport utility vehicle while it was parked at a strip club, and police disclosed that Whittaker not only frequented strip clubs but was also a high-stakes gambler - which is why he was carrying so much cash.
The break-in was the first of several thefts involving Whittaker's vehicle, his office and his house in Scott Depot, a booming bedroom community of about 8,000 situated between Charleston and Huntington, West Virginia's two biggest cities.
One of the thefts occurred at his home on the same day an 18-year-old friend of Whittaker's granddaughter was found dead there. The death remains under investigation. Whittaker was out of town at the time, but the young man's death made the lottery winner part of yet another front-page story.
Last week, Whittaker reported that his 17-year-old granddaughter was missing. The family had not seen or heard from Brandi Lasha Bragg since Dec. 4. Authorities are investigating.
In May, two men sued Whittaker, claiming they were injured when they were tossed out of a nightclub at his request. In another lawsuit, three female employees of a racetrack claim Whittaker assaulted them last year.
On Monday, Whittaker pleaded no contest to a battery charge and was fined $100 and ordered to begin attending weekly Alcoholics Anonymous meetings within 15 days. He was accused of threatening and assaulting a bar manager in January.
"As if we needed another hit on our image as a backward, hillbilly state, along comes Jack Whittaker to reinforce the comedy cracks like Jay Leno makes," groused Dewey Large of Princeton. "This clown is not capable of handling a $10 bill, much less all those millions. Every time you turn around he's having trouble with the laws of our state. What a waste of all that money."
Whittaker has donated more than $20 million to charity since winning the lottery, said his lawyer, Norm Daniels.
Today, his charitable foundation is closed, according to a secretary at Whittaker's company. The legal troubles have raised questions about whether he will be able to fulfill his many promises to help others.
Whittaker declined comment Monday, and his lawyers did not respond to requests for an interview. He told The Associated Press last year that he had been bombarded with requests for help, and the fame was taking a toll on his family.
"If I had to do it all over, I'd be more secluded about it," he said. "I'd do the same things, but I'd be a little more quiet."
Whittaker's wife, Jewel Whittaker, told the Charleston Gazette she regrets the win that thrust the family into the public spotlight.
"I wish all of this never would have happened," Jewel Whittaker said. "I wish I would have torn the ticket up."
Lottery winners commonly regret being so public about their windfalls, said Susan Bradley, founder of the Sudden Money Institute in Palm Beach Gardens, Fla.
"You're really in an international spotlight," Bradley said. "The expectations of you are just - it never ends. It's exaggerated by anyone who feels they are entitled or have an opportunity to grab a piece of it."
As for Whittaker, "I think it's pretty sad, really," said Jerry Medley of Hurricane. "It just goes to show money can't always buy happiness." He added: "I don't have no bad feelings about the guy. I just hope he gets his life straight. I think he could do some good with the money."
By Kelley Schoonover