Lifestyle

Inside expensive downward spiral of the $315 million Powerball winner

Luck was the last thing that Jack Whittaker needed.

In fact, it was so-called good fortune that set off the decimation of Whittaker, who died June 27 at the age of 72.

The problems began on the night of Christmas 2002, when the Putnam County, W. Va., construction entrepreneur won a record-setting Powerball jackpot. Rather than breaking up his $315 million prize into dozens of payments, he took $113 million — after taxes — in a single, lump sum.

Whittaker, 55 at the time, was already worth $17 million. But in the years following his Powerball hit, his life took a seemingly cursed turn: He had hundreds of thousands of dollars stolen from him, endured multiple family tragedies — including the horrific death of his granddaughter, had people try to drug him, saw his home burn down, and turned into a first-class jerk.

He once complained to the Associated Press that, “I’m only going to be remembered as the lunatic who won the lottery.” But really, Whittaker, who died of natural causes, might be remembered as Powerball’s unluckiest winner.

He did nothing to make things easier for himself.

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Whittaker with his check after winning Powerball lottery.
Whittaker with his check after winning Powerball lottery.REUTERS/John Sommers II
Whittaker with his wife Jewell and their granddaughter Brandi Bragg.
Whittaker with his wife Jewell and their granddaughter Brandi Bragg.AP Photo /Stuart Ramson
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“Jack Whittaker was a complete wacko,” Bob Rufus told The Post. A retired forensic accountant, Rufus investigated and worked with the lotto winner during a contentious divorce from his wife, Jewell. (Jack filed for the split in 2005.) “I remember him being in a heated dispute with Jewell’s lawyer, who said to Jack: ‘You confused your IQ with the amount of your lottery winning.’”

At that, Rufus remembered, “Jack was ready to start throwing punches. He was very volatile.”

After winning, Whittaker vowed that the prize would not change him. A week later, he showed up at the Pink Pony, a strip club near his home, and slammed $50,000 in cash on the bar.

“My worst nightmare was waking up in the morning and reading in the paper that Jack Whittaker got rolled at the Pink Pony,” the bar’s manager told the Washington Post. “I said, ‘Please put that money away . . . ’”

Whitaker became more brazen. On another visit to the club, months later, he bragged about having $545,000 stashed in his Lincoln out in the parking lot. Two employees allegedly slipped a mickey into his drink, broke into the vehicle and stole the cash. (They were charged but never indicted.) Whittaker got a bit of good luck when the cash was found near a dumpster.

But five months later, $200,000 was taken from the same car in the same parking lot. Flash forward to 2018, when $100,000 was heisted out of his auto while it was parked in front of his house.

Around the county, Whittaker became known for newly caddish ways. According to the Washington Post, while boozing it up at a local bar, he loudly offered one female bartender money for sex. He later proffered $10,000 to another bartender if she would pose for him in her underwear. (Both women turned him down.)

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Whittaker in the parking lot of The Pink Pony after somebody broke into his car.
Whittaker in the parking lot of The Pink Pony after somebody broke into his car.AP Photo/The Charleston Daily Mail, Chips Ellis
Kanawha County police officers with Whittaker's recovered money.AP Photo/Charleston Daily Mail, Chip Ellis
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Meanwhile, things were not going well at home. In 2004, a friend of his teenage granddaughter, Brandi, was found lifeless from a drug overdose in Whittaker’s house. Later that year, Brandi, who was said to be the apple of Whittaker’s eye, was discovered dead — her body wrapped in a plastic tarp behind a derelict van — from undisclosed causes.

“He gave a crazy stipend to his 17-year-old granddaughter and that attracted some bad characters; nothing good came of it,” said Rufus of the girl who, according to the West Virginia Gazette, received $2,000 per week and was gifted four cars by her grandfather.

Whittaker loved gambling — and that, too, proved disastrous when Caesars Atlantic City sued him for bouncing a $1.5 million check written to cover his losses.

Following another casino imbroglio, he settled with a woman who accused him of sexually assaulting her at Tri-State Racetrack and Gaming Center in Charleston, W. Va. Then, in 2007, Whittaker said he could not pay because he was broke. He insisted that, according to CBS News, a “team of crooks” cashed fraudulent checks “and got all my money.” He and the bank where it supposedly happened settled their differences later that year.

Things seemed to quiet down for Whittaker for a few years — until his home burned down in 2016.

“All of the stories are true,” said Rufus of Whittaker, who ended up dying of natural causes.

“What happened to Jack would be humiliating to a normal person. But he felt like he was above it all as a result of financial worth. I think his reflection would be that he was a victim of the lottery. It certainly wrecked his life.”