The endless tragedies of Powerball winner Jack Whittaker

When Jack Whittaker looked back at his time on Earth, he probably considered Christmas Day, 2002, to be the worst day of his life. That was the day he won a $313 million Powerball drawing, which at the time was the largest lottery prize in American history.

He initially celebrated his big win as a miracle, but to say that his life took a turn for the worse after collecting his jackpot would be a severe understatement.

While we've seen other winners experience a wide range of tragedies, ranging from prison to murder to kidnappings, few people have ever gone through as much unbroken bad fortune as the West Virginia resident who once thought he was the luckiest man in the world.

This is the true story of the lottery fortune that ruined Jack Whittaker's life.

The builder

Before he became a cautionary tale, Whittaker was someone whom other people looked to as a source of inspiration. He was raised in poverty in West Virginia, telling reporters:

I grew up very, very poor in Jumping Branch, W.Va. We never had a lot of luxuries. We never had a car. We didn't have a TV until later in life.

However, by the time he was 55, Whittaker was the president of Diversified Enterprises Construction, a contracting firm that laid water and sewer pipes throughout West Virginia.

The company generated millions of dollars in business every year, employed over 100 workers, and gave Whittaker a life he could only dream of when his family was too poor even to buy him a winter coat.

Whittaker's family life was also enviable. He married his childhood sweetheart, Jewel, and together they had one daughter, Ginger. Ginger made them grandparents when she gave birth to her daughter, Brandi, and she quickly became the center of Whittaker's life.

Friends say that when he wasn't working, he would always make time for his granddaughter, and they loved to lie in bed together, eating popcorn and watching TV. With a successful business and a loving family, Whittaker seemed like a man who had everything.

And then, on Christmas Eve, 2002, he made a decision that destroyed everything he had spent his entire life building. He bought a lottery ticket.

The winner

Whittaker was a regular at the C&L Super Serve grocery store in Hurricane, West Virginia, where he was known as 'the Cowboy Man' because he always wore a black cowboy hat. He would stop in early every morning on his way to work and buy his usual breakfast of two biscuits and bacon sandwiches.

He wasn't a regular lottery player, but he knew that the Powerball jackpot had grown to over $300 million, and he decided to buy $100 worth of tickets for the Christmas Eve drawing.

That night, he fell asleep before the winning numbers were announced, but when he woke up the next morning, he checked his ticket and realized that he had won the jackpot and that his whole life was about to change. Whittaker told reporters:

I got sick at [sic] my stomach, and I just was [at] a loss for words and advice. You know, I was really searching for advice, and it's, like, Christmas Day.

He chose the one-time cash payout and took home $113 million after taxes. While this is an immense sum of money for everyone, Whittaker was already financially successful, and most people believed he had the experience necessary to manage his new fortune.

The giver

West Virginia is one of the poorest states in America, and Whittaker's first instinct was to use his money for good. He stated:

I wanted to build churches. I wanted to get people food that didn't have food. I wanted to provide clothing for children that [sic] needed clothing.

Whittaker was incredibly generous with his wealth, and some reports indicate that he gave away $50 million to people in need, including $15 million he donated to build two new churches in his community.

So many people asked him for money that he launched a non-profit foundation to manage the requests. Jill, a woman he hired to help run his foundation, said they received more letters requesting help than they could even read. Jill told reporters:

There were so many letters that they wouldn't even deliver the mail. It was nothing for us to sit for 10 hours just opening envelopes.

He was also generous with the people he credited with helping him win, and he bought the store clerk who sold him the ticket a Jeep Grand Cherokee, a new house and gave her a check for $44,000.

The downside of his generosity was that Whittaker felt like he couldn't go anywhere without people begging, demanding and sometimes even threatening him to give them money. He had to change his daily routines and hired off-duty sheriff's deputies to provide security for him and his family.

Party hard

While Whittaker did show substantial generosity, he also decided that after a lifetime of hard work, he was ready to party like a rock star. He purchased a fleet of luxury cars, including a Lamborghini that he would drive through neighborhoods while throwing cash out the window.

He also became a high-rolling gambler and would frequently travel to Atlantic City and local casinos, where he would drink and blow through hundreds of thousands of dollars in a single night.

He became a regular customer at the Pink Pony strip club, and shortly after his win, he walked into the establishment, threw $50,000 in cash on the bar, and said he was there to have a good time.

Whittaker drank heavily following his win, and one time, state troopers found him passed out behind the wheel of a green Cadillac parked on the side of the road. They determined he was impaired and arrested him for driving under the influence.

Friends reported that a man who once prided himself on his appearance was suddenly slovenly, and his once neat clothes were a mess.

His personality changed as well. He had money and wanted everyone to know it. He once offered a bartender $10,000 to model for him in her underwear. He made it clear to everyone that he felt like his wealth entitled him to buy people.

Money problems

They say with money, easy come, easy go, and with Whittaker, the money went fast, whether he meant it to or not.

On a night out at the Pink Pony, he loudly bragged that he had over half a million dollars in cash in a briefcase in his Cadillac Escalade parked outside. An hour later, two club employees allegedly drugged him, broke into his car, and stole the money.

He was fortunate to recover the money, but he never seemed to learn the lesson about not keeping cash in his vehicle because just a few months later, he was at another strip club when thieves again broke into his SUV and stole $200,000 in cash.

In a separate incident, thieves broke into his car when it was parked outside his house and stole another $100,000 in cash.

His business also suffered as news of his win spread. While his company had a reputation for doing high-quality work, he faced an onslaught of lawsuits from disgruntled clients shortly after his win.

Rob Dunlap, an attorney for his business, stated that he had to spend at least $3 million fighting legal claims against him. Whittaker said that the lawsuits had nothing to do with the quality of his work and that people were simply trying to take advantage of his wealth.

"I've had over 400 legal claims made on me or one of my companies since I've won the lottery, " he said. He was also sued by Caesar's Casino in Atlantic City for writing a bad check to cover gambling losses of $1.5 million.

His biggest financial disaster occurred when Whittaker claimed that a group of criminals stole his checkbook and wrote out different checks for several hundred thousand dollars. The group then went to different banks on the same day and cashed the checks simultaneously, draining their bank accounts in a single day.

It wasn't just Whittaker who was a target of thieves. More than once, people whom he gave large sums of money to reported being robbed shortly afterwards. It was as if the money was cursed, and something bad happened to everyone who received it.

Death

Perhaps the person who suffered most from Whittaker's big win was his beloved granddaughter Brandi. She was fifteen when Whittaker pulled her out of school for her safety.

The money became like a barrier between Brandi and her old social circle, and she quickly lost most of her friends. Lonely and without school to give her life structure, she would sleep all day and drive around for hours at night in the new Mitsubishi Eclipse with a custom blue paint job that Whittaker gifted her.

As part of his generosity, he gave her a credit card and thousands of dollars in cash a month, but was so busy with his own drinking and partying that he barely gave her any adult supervision.

Lonely and with more money than she knew what to do with, Brandi quickly attracted the wrong type of people in her life, who were more interested in what she could buy them than who she was.

She became a drug addict, starting with pills and marijuana, but quickly graduating to crack and finally injectable drugs. Friends said her new car was always full of junk food wrappers and loose cash leftover from her endless shopping sprees.

Her family sent her to rehab several times, but she would always come home and relapse because Whittaker kept giving her money, and no one would watch over her. Other teenagers would spend time with her just because she would buy them drugs.

She briefly dated a local boy named Jessie Joe Tribble. They would frequently do drugs together, which she bought for him. He tried to break away from his drug habit by taking a job in his dad's shop and even considered joining the military, but ultimately, the power of his addictions was too much to overcome.

One day, he didn't come back after a lunch break, and his family couldn't find him. Authorities discovered him dead of an overdose in a bed in a house owned by Whittaker, where Brandi would frequently invite friends over to party. An autopsy revealed a cocktail of drugs in his system, including Oxycodone, methadone, meperidine, and cocaine.

Jessie's friends blamed Brandi for his death, and they wouldn't let her into the funeral home when she tried to attend Jessie's wake.

Following Jessie's death, Brandi was even more isolated and spiraled deeper into drug addiction. In the winter of 2004, her family reported her missing. Police searched for her until they discovered her dead body wrapped in a plastic sheet that was hidden behind an abandoned van. While her cause of death was never fully determined, it was likely that she also died of a drug overdose.

Brandi was buried on Christmas Eve 2004, two years to the date after Whittaker bought his winning Powerball ticket.

The end

The death of his beloved granddaughter was not the end of Whittaker's troubles. Jewel finally had enough of his drinking, partying, and arrogance, and she divorced him in 2008, ending their 42-year marriage.

The legal cost of the divorce and financial settlement drained most of his remaining wealth and contributed to his bouncing a $1.5 million check to Caesar's Casino.

In 2009, his daughter Ginger passed away from cancer at the age of 42. While her death had nothing to do with his lottery win, it was yet another tragedy he had to endure, this time without his wife by his side.

In 2016, a mansion he owned caught on fire while Jewel was inside. She managed to escape, but firefighters were unable to save the home, and it was declared a total loss. Whittaker died on June 27, 2020, after a long illness. He was 72 years old. He had few friends and very little money at the time of his passing.

Reflecting on his misfortunes a few years before his death, he told reporters:

I'm only going to be remembered as the lunatic who won the lottery. Since I won the lottery, I think there is no control for [sic] greed. I think if you have something, there's always someone else that [sic] wants it. I wish I'd torn that ticket up.