The Story of Jack Whittaker: The Man Who Won the Largest Jackpot Ever and Lost Everything (6 photos)

There are countless stories of lottery winners whose massive windfalls turned into curses. Typically, instant millionaires are undone by vanity, a taste for luxury, and reckless spending. But the story of American Andrew "Jack" Whittaker is different. He hit the largest jackpot in history, only to fall victim to his own generosity.





Lucky Mr. Whittaker

Andrew "Jack" Whittaker was born and raised in a small town in West Virginia. His family was dirt poor—his parents couldn't afford a car, let alone a TV set. As a boy, Jack swore he would break out of poverty and build a respectable life. He succeeded, becoming a self-made millionaire by age 55. He had everything a man could want: a thriving construction business, a magnificent home, a loving wife, a daughter, and a granddaughter.



It all started to fall apart on Christmas morning in 2002. Jack discovered that a Powerball ticket he bought with spare change at a gas station had won $314,900,000. What could possibly go wrong, you might ask? Even for a millionaire, a third of a billion dollars is a life-changing fortune. Whittaker thought so too, completely unaware of how the dream would turn into a nightmare.

“I remember my stomach hurt, and I honestly didn’t know what to do next or who to talk to.”

Powerball officials stepped in to help him navigate his new reality. The following morning, Jack was posing for the press with a giant lottery check and giving interviews. Overwhelmed and bewildered, the lucky winner stammered through reporters' questions about how he would spend the money, rambling about charity and buying gifts for his daughter and granddaughter.





Jack Whittaker with his wife and granddaughter

Whittaker was true to his word. As soon as he received the payout, he funded the construction of two churches in West Virginia. He also established the Jack Whittaker Foundation to assist those in need. There was no shortage of people seeking financial help; they came in an endless stream, each carrying a heartbreaking sob story.

People begged, pleaded, persuaded, and even demanded money from Jack. Whittaker found it baffling how many acted as if he were somehow responsible for their poverty. Still, he kept handing out cash, eventually giving away roughly $50 million. When the philanthropist began to rein in his generosity and become more selective, the lawsuits started pouring in. It wasn't just the foundation—shrewd lawyers targeted every invoice and business transaction made by Whittaker's company.



The Cursed Millions

Things were spiraling at home, too. Relatives resented what they saw as a waste of money, firmly believing Jack should look after his own family before helping strangers off the street. Even though he took care of them, many felt it wasn't enough and accused Whittaker of being stingy.

Jack gave his granddaughter an allowance of $2,000 a week. Flushed with cash and no limits, the young girl developed a severe drug addiction. Meanwhile, Whittaker suffered from loneliness and boredom. Endless litigation forced him to shut down his business and ruined his relationships with business partners. He didn't even have anyone to grab a drink with at a bar—everyone had turned their backs on him. Jack began drinking alone.



At first he frequented neighborhood bars, but soon he was spotted in casinos and strip clubs. Jack fell down a slippery slope and was rarely seen sober. He racked up multiple DUI arrests and paid steep fines. A year after the ill-fated win, Whittaker walked into a police station to report that a briefcase containing half a million dollars in cash had been stolen from his car. Naturally, officers asked why he was driving around with that kind of money. Jack simply replied, "Because I can."

It was clear his life was unraveling, but the worst was yet to come. On December 9, 2004, his granddaughter went missing. Ten days later, her body—wrapped in plastic—was discovered in a supermarket parking lot. An autopsy revealed she had died of a drug overdose. A few years later, Whittaker lost his daughter, who died under mysterious circumstances. Then, in 2016, a fire gutted his home, leaving virtually nothing behind.



Today, Jack Whittaker shuns the media, and little is known about his current life. No one even knows if anything remains of those ill-fated millions. In his final interview, he admitted he wished he had torn up that cursed lottery ticket and thrown it away—the ticket that cost him everything.