23 December 2023 , 07:00
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A man who won a whopping $315million (£250m) on the lottery made one mistake which led to 17 years of tragedy and ultimately his death.
Jack Whittaker, a former construction engineer from Putnam County, West Virginia, won the Powerball jackpot on Christmas 2002.
From there on, his
saw family tragedies - including the terrible death of his granddaughter - hundreds of thousands of dollars stolen, a fire which destroyed his home, and people attempting to spike him.
He made a number of mistakes but the one that led to the most tragedy was that he would flash the cash wherever he went. And with that he and his family became a target.
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He vowed the prize would never change him but a week after the win he turned up at Pink Pony, his local strip club, and stuck $50,000 (£40,000) on the bar in cash.
Andrew Jackson aka Jack Whittaker waves as he gets into his rented limousine during a visit to New York City after winning the $314.9million Powerball jackpot (NY Daily News via Getty Images)The bar manager told the Washington Post at the time: “My worst nightmare was waking up in the morning and reading in the paper that Jack Whittaker got rolled [robbed] at the Pink Pony,” the bar’s manager told the Washington Post. “I said, ‘Please put that money away . . .’”
It wasn’t long before the manager’s fears turned to reality. Months later, he returned to the Pink Pony and bragged of the $545,000 (£430,000) he had stashed in his Lincoln outside. Two employees are alleged to have spiked him, broken into the vehicle and stolen the cash - despite being charged they never saw prison. The cash was later found near a dumpster, a rare stroke of post-win luck for Whittaker.
Jack Whittaker later said he wished he had ripped up the ticket (AP Photo)Whittaker never went long without being the talk of the town. Five months later, $200,000 was taken from the same car, again in the Pink Pony parking lot. In 2018, another $100,000 was stolen when his car was parked outside his house.
His first mistake was failing to break up his prize winnings into multiple payments over time - and he instead took an after-tax single lump sum of $113 million home.
He became notorious in the area for brash spending, gambling, bar fights, and unwanted sexual propositions. Whittaker, who passed away on June 27 2020 aged 72, may be one of the Powerball’s unluckiest - and unpopular - winners.
Jack with daughter Ginger McMahan, granddaughter Brandi Bragg, 15, and wife Jewell (NY Daily News via Getty Images)Whittaker became a local celebrity - perhaps more infamous than famous - and became known for his newfound boisterous arrogance. The Washington Post reported Whittaker loudly offering one female bartender money for sex, and offering $10,000 to another bartender if she posed for him in her underwear. He was, of course, rejected by both.
But things at home were not quite the flashy story of money, sex, clubs and cars. In fact, in 2004 it took a tragic turn, with the devastating death of Whittaker’s teenage granddaughter Brandi - believed to be the apple of his eye.
Earlier in the year, Brandi’s friend was found dead from a drug overdose in Whittaker’s house. And later that year, Brandi was discovered dead, her body wrapped in plastic tarpaulin behind an abandoned van.
Rufus recalled that Whittaker gave huge sums of money to his granddaughter - which he believes may have been related to the tragedy. “He gave a crazy stipend to his 17-year-old granddaughter and that attracted some bad characters; nothing good came of it,” he said. According to the West Virginia Gazette, Brandi received $2,000 per week and was gifted four cars by Whittaker.
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Jack with Brandi in happier times (Getty Images)Over the next years he continued to enjoy gambling, which saw him embroiled in a legal battle with Caesars Atlantic City for bouncing a check for $1.5 million - which he didn’t have. He was also accused of sexual assault in a casino - he settled the case, before saying in 2007 he could not pay as he was broke. His life appeared to have settled down after that - until his house burned down in 2016.
Whittaker and his wife once said that if they could travel back in time, they would tear the ticket up. Whittaker felt he would only be remembered as the “lunatic who won the lottery”.
Whittaker did not throw all of his money away, and donated a fair chunk of it to charitable causes. As a religious man, he donated $15million to build two churches. He also created the Jack Whittaker Foundation, sending cheques to cover people’s house and car payments along with other expenses. To receive a cheque, people only had to ask.