Mount Hope, W.Va. – In his darkest moments, Jack Whittaker has sometimes wondered whether winning the nearly $315 million Powerball game was really worth it.
The jackpot that was the stuff of dreams turned into a nightmare: His wife left him, and his drug-addicted granddaughter – his protégé and heir – died. He endured constant requests for money.
Almost five years later, Whittaker is left with things money can’t cure: His daughter’s cancer, a long list of indiscretions documented in newspapers and court records, and an inability to trust others.
“I don’t have any friends,” he said in lengthy interview. “Every friend that I’ve had, practically, has wanted to borrow money or something and, of course, once they borrow money from you, you can’t be friends anymore.”
Whittaker was a self-made millionaire long before he became a lottery winner, having built a pipeline business worth $17 million. Then he hit the Powerball in December 2002. It was then the largest-single jackpot ever.
The prize was worth $314.9 million. Whittaker opted for the lump-sum payout of $170 million – $93 million after taxes.
He still has plenty of money. And instead of retiring, the 59-year-old starts his day at 5 a.m., juggling ventures in construction, real estate, used cars, even movies. Work is the last remnant of his old life.
“Nothing else is normal,” he said, sounding simultaneously gruff and sad.
His family has always been well-off. But winning the Powerball brought instant celebrity status.
Whittaker’s struggles with drinking, gambling and philandering became public, and tales of his transgressions were retold with relish.
His home and car were repeatedly burglarized. At a strip club, thieves broke into his Lincoln Navigator and stole a briefcase stuffed with $245,000 in $100 bills and three $100,000 cashiers checks. The briefcase was later found, with the money.
Whittaker was charged twice with driving while under the influence and sued repeatedly, once by three female casino employees who accused him of assault.
In all, Whittaker says, he has been involved in 460 legal actions since winning. He recently settled a lawsuit that alleged his bank failed to catch $50,000 in counterfeit checks cashed from his accounts.
He believes he has been unfairly demonized by the media, which he says exaggerated his problems and helped drive his wife away.
“I don’t know any normal person who could have a marriage with everything that’s been written about me that’s not true,” he said.
The couple’s daughter, Ginger McMahan, has battled cancer for years. The disease is in remission, though she remains in poor health.
His granddaughter, Brandi Bragg, was to inherit his businesses when she turned 21. She died of a drug overdose at 17. Whittaker blames her problems on a kidnapping threat, which led to home schooling, and her decision to run with an older crowd.
Before Powerball, Whittaker and his wife went to church. These days, he seldom does.
“It’s just aggravating, you know. People come up and ask you for money all the time, tell you some kind of a sob story.”
Whittaker says he hasn’t been stingy. The Jack Whittaker Foundation has spent $23 million building two churches. His family donates food, clothing and college scholarships to local students.
But Whittaker has little doubt as to his own legacy.
“I’m only going to be remembered as the lunatic who won the lottery,” he said. “I’m not proud of that. I wanted to be remembered as someone who helped a lot of people.”
