‘I regretted winning £235m on Powerball – the dark side turned me into a lunatic’

The Powerball lottery is coming to the UK this week and one previous winner regrets his jackpot after scooping £235m, as family tragedy and personal turmoil left him wishing he had never played

The world’s largest lottery is arriving in the UK this week – and a fortunate Brit could shortly find themselves over £300million wealthier. Powerball is an American lottery game where winners receive enormous prizes distributed across three decades.

Today (July 23) marks the inaugural UK draw with an estimated jackpot exceeding £300m – the biggest prize ever on offer in this country. Allwyn, the National Lottery operator, has made the game accessible to UK participants, who will compete alongside players in the US.

There is one former Powerball millionaire who understands precisely what it feels like to win an astronomical sum of money – yet it turned out to be the most devastating thing that ever befell him.

Andrew ‘Jack’ Whittaker wished he had destroyed the ticket that resulted in tragic family fatalities, a bitter divorce, multiple robberies and a troubling gambling dependency.

Below, we examine the haunting dark side Whittaker endured from his windfall.

Jack Whittaker

On Christmas Eve 2002, Whittaker bought a ticket at a supermarket in his hometown of Hurricane, West Virginia, US, after stopping to fill up his car with petrol.

Despite not being a regular participant, he hit the jackpot, and it was the largest ever single winning ticket in US lottery history – $315m (£235m).

Yet, this was not a rags to riches tale, because Whittaker, an American businessman who operated a thriving construction firm, was already worth a substantial $17m (£12.7m). Despite possessing experience managing considerable wealth, the Powerball jackpot proved too much to handle, and it wasn’t long before his life began to unravel.

Rather than splitting the winnings into multiple instalments over time, he chose a lump sum as his preferred option, and walked away with $113m (£84m) after tax.

He wasn’t greedy with his fortune, and invested $15m constructing two churches, while also establishing the Jack Whittaker Foundation, through which he would send individuals money to help with things like vehicle payments and other costs.

Nevertheless, many viewed him as an unlikeable victor, and Bob Rufus, a divorce accountant, recalled witnessing an argument between Whittaker and his wife’s divorce solicitor.

He remembered: “Jack was ready to start throwing punches. He was very volatile.”

The Powerball victor initially vowed that the winnings would not alter him as an individual – and he told Fox News that he was “doing God’s work with all this money” before adding: “I am helping a lot of people and I plan to help a lot more.”

Yet, following the windfall, he quickly appeared at his local strip club, Pink Pony, where he placed $50,000 (£37,500) in cash behind the bar.

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

He subsequently returned to Pink Pony and reportedly began boasting that he had over a million in cash stashed inside his Lincoln parked outside the establishment.

According to accounts, two individuals then drugged him before breaking into the vehicle to steal the money. Both were prosecuted but avoided jail time and the cash was later discovered beside a rubbish bin.

Remarkably, Whittaker didn’t heed the warning, and $200,000 (£150,000) was nicked from the identical car outside the very same strip club merely five months afterwards.

Whittaker became both celebrated and notorious locally and following the lottery triumph he purchased a Lamborghini and gained a reputation for hurling cash from the window.

Following numerous thefts of substantial amounts of money that he carried about, he was questioned why he persisted in doing so, and he answered: “Because I can.”

Merely two years after striking it rich, Whittaker lost his granddaughter, Brandi Bragg, who was only 17.

Brandi was discovered in a plastic tarpaulin behind a deserted van. Whittaker was reportedly providing his granddaughter with $2,000 (£1.5k) weekly prior to her death while also purchasing her four vehicles.

Divorce accountant Bob Rufus commented: “He gave a crazy stipend to his 17-year-old granddaughter and that attracted some bad characters: nothing good came of it.”

While nothing can match the loss of a beloved family member, Whittaker’s existence continued to collapse. This included facing legal action from Caesars Atlantic City casino after he bounced a cheque for $1.5m (£1.2m) to settle gambling debts.

And in 2008, following 42 years of matrimony, Jewell Whittaker initiated divorce proceedings.

It proved to be a bitter and protracted battle and, in 2011, the Supreme Court determined that his former wife was entitled to rights and access to portions of her ex-husband’s business assets.

Whittaker also suffered the loss of his daughter, 42-year-old Ginger Whittaker Bragg, who was Brandi’s mother, in 2009.

He revealed to ABC News that he harboured significant remorse about his Powerball victory and stated: “I pretty much lost everything I had and held dear in my life.

“Money has never meant anything to me. You have to have money to exist in this world, but money doesn’t rule the world. Money is not what makes people happy.”

Whittaker, whose home was also destroyed by fire in 2016, continued: “My wife said she wished she’d torn the ticket up and I wish I had torn the ticket up too. I just don’t like what I’ve become.”

According to The Washington Post, he once brazenly propositioned a female barmaid with cash for sex, while also offering another woman behind the bar $10,000 (£7,500) to pose in her underwear.

He was also previously accused of sexual assault in a case that was settled before he claimed in 2007 that he was too impoverished to make payment.

Whittaker once revealed to the Associated Press: “I’m only going to be remembered as the lunatic who won the lottery.”

He passed away from natural causes at the age of 72 in June of 2020.