A￼ndrew ‘Jack’ Whittaker was a larger than life character.
A real-life cowboy who dressed all in black like Johnny Cash, Jack, 55, was cheerful and polite.
He came from a poor family and started work in construction at the age of 14 to help put food on the table.
After years of back-breaking work, he had the experience and drive to start his own water and sewer pipe business, going on to employ more than 100 people. Through sheer determination, Jack had achieved financial stability.
With his beloved wife of 40 years, Jewell, their daughter, Ginger, and granddaughter, Brandi, by his side, Jack was a contented man.
Then just before Christmas in 2002, Jack walked into his local service station.
Brenda Higginbotham, the cashier, greeted him with a smile and good-natured teasing like she did every morning when Jack arrived to get breakfast before work.
But this day, Jack noticed there was a Powerball jackpot up for grabs, so he bought a ticket as well. That decision would change his life forever…
On Christmas Day, Jack won $440 million – the largest undivided lottery jackpot in history.
Within days, Jack’s charisma, frequent media appearances and pledge to dedicate millions towards building a new church and supporting underprivileged locals catapulted him into celebrity status.
Jack loudly and proudly declared the win wouldn’t change him and he’d keep his feet firmly planted on the ground.
‘I want to be a good example. I want to promote good will and help people,’ Jack told reporters.
But just a week later, the manager of a local strip club said Jack slapped $70,000 in cash on the bar and saw in the New Year through a haze of booze and women.
He did make good on his promise to help people, creating the Jack Whittaker Foundation and sharing almost $10 million between three churches.
He also built sports fields and playgrounds, and even bought Brenda, the cashier, a new house and car.
Crowds of people began seeking Jack out, all with a sad story to tell and begging for a hand-out.
‘A lot of them, they had cancer or their child was dying,’ Brenda said.
After being continually harassed Jack stopped going in for breakfast. His commitment to remain humble and use his windfall to spend more time with his family was soon forgotten.
Instead, he spent more and more time hanging out with his new party-hard friends at casinos and bars.
Accusations of sexual harassment and public belligerence emerged, followed by car accidents, drink driving charges and multiple lawsuits.
Jewell, a quiet, God-fearing woman, was devastated.
Showered with money, Jack’s adored and doted-on granddaughter Brandi, 16, lost friends, went off the rails and turned to drugs.
‘Before the lottery, she was normal,’ said Tim Cobb, one of Brandi’s friends. ‘She let the money go to her head.’
Brandi’s money attracted a new crowd and she became distrustful, never sure if the people were genuine or just there for the gifts and drugs she could buy.
‘They want her for her money and not for her good personality,’ Jack said. ‘She’s the most bitter 16-year-old I know.’
Then, Brandi’s boyfriend Jessie died from an overdose, in Jack’s house.
Just as suddenly as Jack’s star had risen, community opinion of their hero cowboy darkened and Jack became the topic of rumour and gossip. People felt that Jack thought his money made him better than everyone else.
Unable to handle Jack’s descent into debauchery, the final straw for Jewell came in November 2004 when Jack crashed his car into a concrete median strip and was again charged with driving under the influence.
Jewell kicked him out and changed the locks, telling reporters she wished they’d torn up that lottery ticket.
Then, Brandi stopped showing up at Jack’s office to collect her daily cheque.
Concerned, Jack reported his granddaughter missing and 11 days later, just shy of two years since Jack’s win, Brandi’s body was found.
Although it was never confirmed, it’s suspected she had also overdosed.
‘My granddaughter is dead because of the money,’ Jack said during an interview with ABC News. ‘She was the shining star of my life, and she was what it was all about for me.’
By 2007, Jack was broke and unable to pay the numerous lawsuits that had been filed against him.
In 2009, his daughter Ginger, Brandi’s mother, was found dead at her home, aged 42, but her cause of death is still unconfirmed.
Then in 2016, Jack’s house burned down and he wasn’t insured.
Since then, it appears Jack hasn’t given any interviews.
‘At first I didn’t think anything would change, but everything has changed,’ Jack said previously. ‘My wife said she wished that she had torn the ticket up. Well, I wish that we tore the ticket up too.’
Read more in this week's issue of that's life, on sale now.
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