What would you do if you found yourself winning millions upon millions of dollars? It sounds like a dream, but it isn’t always what it’s cracked up to be. When contractor Jack Whittaker purchased $100 worth of lottery tickets from a gas station convenience store near his home in West Virginia, he never expected it to take over his life in the way it did.
The lottery exists so people can live out their fantasies of striking it rich without working on getting there, but Whittaker was already independently wealthy. In fact, he cited his lottery win as why his life later fell apart. The man just never managed to recover from the significant letdown he encountered as a result of hitting the jackpot.
Jack Whittaker was a self-made man before becoming the winner of one of America’s most enormous Powerball lottery pots. Born Andrew Jackson Whittaker Jr. on October 9th, 1947, in Jumping Branch, West Virginia, there was no way that he could have known the fate he would meet later in life.
He met the love of his life as a young child in grade school, and the two were married almost instantly out of high school. He was a man of faith and was committed to serving his church community. He built his own construction company from scratch, raised a family, and had an overall successful life before everything started going downhill.
Whittaker was known for dressing in his sleek country style – he frequently sported all-black outfits, complete with his signature cowboy hat. His style was often compared to that of Johnny Cash, the legendary musician. His look was how many people in his town identified him.
Everyone around town knew who he was – the family man who worked in construction. He lived in a modest home to start, drove a truck, and stopped for sandwiches at his local deli, just like anyone else in town. He was just another resident of their town, resembling the uniform of many men in the Midwest at the time.
He was known for his easygoing demeanor, with the checkout girl at his local C&L Super Serve in Hurricane, West Virginia, describing him as “polite and cheerful, as if trouble were a stranger.” He was well known around town, but little did he know, he would soon be known for so much more.
Just a few days before Christmas in 2002, Whittaker pulled his truck up at his usual time, just before 6:30 am. Brenda Higginbotham, the 39-year-old “biscuit lady,” would see her favorite customer pull in and get his order ready for him. Seeing him always put a smile on her face.
The two joked around like pals who have known each other for years. Every day, he would come in at the same time, fueling up his car and getting his standard breakfast order: two biscuits stuffed with bacon. He ordered it so frequently that whoever was working at the checkout counter at the time knew what he wanted.
The two joked around so frequently that the other store clerks would tease that the two had a type of “rendezvous deal” going on. She would laugh and state, “it ain’t like that!” She said she was just happy to converse with her favorite customer. Despite him being her favorite customer, she didn’t even know his name was Jack!
Just days before Christmas in 2002, Whittaker’s trip to the gas station would change his entire life. In his words, he did not play or buy lottery tickets frequently – only if the jackpot was well over $100,000. He had purchased tickets before and expected very little to come of it.
He only wanted to buy tickets when the jackpot was “worth his while,” (as if anything less than multiple millions would not be worth his while?). His company had earned him a net worth of well over $17 million. Why would Whittaker waste his breath on anything less, especially when he had already built a fortune on his own?
Christmas Day 2002 was a new peak for the sale of lottery ticket purchases. At 3:26 pm, the ticket-buying-madness hit a high note. Convenience stores, gas stations, you name it – they were all selling lottery tickets at warp speed. West Virginia residents were buying as many tickets as possible, averaging at about 15 people buying a ticket per second.
Those purchasing tickets would barely spend more than one dollar in the hopes of making it big. When Whittaker laid out $100 for a bunch of tickets, he didn’t expect much to come of it. It was out of his hands now; his numbers were randomly selected, and he would soon learn what was coming for him.
At around 11 o’clock that Christmas night, Jewell woke her husband to share what she had just learned from Channel 3 out of Charleston, West Virginia. She nudged him until he woke up from his peaceful snooze with some fantastic news: four out of five of his numbers came up as a lottery match!
The Whittaker couple had no clue what the four-number match meant. He knew he must have won at least 100 grand but wasn’t curious enough to get out of bed. The following day, he woke up at 4:30 am in the same routine as usual. He went to his construction job, unsuspecting of his new fate.
The morning of his victory, he showed up to the same job he’s had for years. He began working when he was just a poor 14-year-old living in the hills of West Virginia and went on to build his own construction company, Diversified Enterprises Construction, which earned him a nice chunk of change.
His post as President of the Putnam County company set him up for a financially comfortable life. His net worth before purchasing his winning lottery ticket was already a cool $17 million, so finding out what he’d won only added to his wealth.
The man who employed over 100 people in his business was about to come into a fat chunk of change! Before heading to work, he turned on the television at 5:15 am and learned that the winning Powerball ticket was sold at his local C&L Super Serve. He knew his ticket was a match, but what were the chances?
He didn’t think that it was possible for the little convenience store to be selling multiple winning tickets. What were the chances of that, really? The winning numbers flashed on the television; the numbers the night before were wrong. All five of his numbers had matched the winning set, not just four!
Whittaker had won a whopping $314.9 million! He chose to take a lump sum, taking home a one-time payout of $113,386,407.77, after taxes. At the time, he determined that his life would not change; that he would take the money and comfortably survive while he spent time with his family.
“I just want to thank God for letting me pick the right numbers . . . or letting the machine pick the right numbers,” he told reporters while claiming his prize. He already knew how he would start spending his winnings, and collecting it was just the start. He wasn’t alone, though. His granddaughter, Brandi Bragg, also knew how she wanted to spend the money.
To start things off on the right note, Whittaker ran back to the C&L Super Serve and instantly tipped Brenda, the girl who constantly served him and helped him. He handed her a $100 bill, and she too was shocked to learn that he won the big jackpot. He followed his best impulses to try and use the money for good – to start, at least.
His granddaughter, Brandi, was just 15 years old at the time. The family appeared on a half-hour live broadcast and a series of other morning talk shows. In one of these appearances, Brandi announced she wanted to use her grandfather’s winnings to meet the rap star Nelly and buy a blue Mitsubishi Eclipse.
Brandi would get her dream car and so much more, but that was not part of Whittaker’s first steps after collecting his money. First, he felt the need to pay it forward and help out the woman who served him the winning ticket – who was working for just $6 an hour at her checkout counter.
He went ahead and bought Brenda a house valued at $123,000 in a nice neighborhood nearby. He also bought her a brand new Jeep Cherokee and handed her a check for $45,000. He wouldn’t have won a thing without her selling him the winning ticket!
When reporters asked what he would do with the money as a whole, he was adamant that he intended to invest in his religious community. He pledged 10% of the overall payout to his local churches, primarily associated with the Church of God. They appreciated everything he did for them.
“I want to be a good example. I want to make people proud of what happens with this winning. I want to promote goodwill and help people,” Whittaker stated. He and his wife were avid churchgoers, and he wanted to help the religious community as they had helped him spiritually through the years.
His funding to the church community paid off; they used the money and built a substantial new house of worship in Hurricane, West Virginia. This specific beneficiary congregation constructed a multi-million-dollar church. They would never have to worry about paying for repairs for their facility again!
It’s important to mention that even with the cost of constructing this expensive establishment, they certainly were not running low on funds after. 10% of his winnings was roughly $13 million, a number which would hopefully take years for their community to burn through, even after building their new church.
One of the last “good impulses,” before everything went south, was creating the Jack Whittaker Foundation. The lottery winner donated $14 million to build a foundation in his name to help those in need in rural West Virginia. He wanted to pay it forward as best as he could.
The foundation provided meals and clothing to those suffering from poverty in the area, which already had the 6th highest poverty rate in the country before the COVID pandemic hit the state in 2020. Back in 2002, the state’s percentage of impoverished people was 17.9% compared to 12.4% nationwide. His foundation was going to help a ton of people.
Whittaker started to spend his money at alarming rates. Outside of his charitable donations, he started giving his granddaughter a hefty allowance. She would be given $2,000 a week at the young age of 17. Not only did she receive a ton of money, but she also got some other big toys.
Whittaker bought her not one, but four cars. When he was asked about it on his 20/20 special, his response was truly priceless. “She can only drive one car at a time… I’m proud of the fact that she’s got four cars!” Alright, grandpa… that sounds like too much. Soon, he would learn that she genuinely overindulged – and paid with her life.
Within a few days of his big win, Whittaker started acting on his virtues. He showed up to his local strip club, The Pink Pony, and put a large sum of cash on the table. How large are we talking? He put $50,000 on the table, and the club owners instantly knew that they were in for some bad news.
By “bad news,” they meant that they knew it would attract trouble. No one had come into the club with that kind of cash, and they knew that him flashing that money would come with consequences. Soon, those in Whittaker’s life would point out changes in his personality – he was suddenly more authoritarian and more impulsive.
Those in his life could point out when Whittaker transitioned from a regular run-of-the-mill guy to a guy who expected things because he had money. Not only did he have high expectations, but he brought large sums of cash with him on most of his outings, which often made him an easy target.
Having a strong personality doesn’t necessarily mean that people won’t try to take advantage of you. Whittaker learned this the hard way, as people started coming out of the woodwork to claim that he owed them financial restitution for all of their struggles in life. He was happy to pay up, but that wasn’t the end of it.
When his granddaughter got her hands on a stack of cash, it seemed that all bets were off. She had toys galore, many cars, and really anything else her heart desired. She started using her money on drugs and other substances, which ultimately led to her demise within a couple of years.
Brandi went on a series of spending sprees after her grandfather hit the jackpot. She would spoil her friends, especially her boyfriend, Jesse Tribble. His father knew that having a girlfriend who would spend that much money on him for anything he wanted would be trouble, and his gut feeling was proven right very quickly.
It seemed that anyone who had ever come in contact with Whittaker was popping up and telling him that he owed them. People came to him sharing their various sob stories, ready for a handout from the man who they felt owed them money.
He didn’t necessarily fall victim to Nigerian princes scamming people on the internet, but scammers came as often as they could. He was robbed multiple times, and whenever he spent time at the racetrack, he would find himself running into trouble again. This was one of the many results of his flashiness.
Whittaker would often carry around ridiculous amounts of money with him. Robbers broke into his truck and stole a briefcase containing $545,000 from the passenger seat. While it seems relatively obvious why you shouldn’t carry that much cash around, his answer for why he did it was simple: “because I can.”
In another incident, two strip club employees, a general manager and a dancer-manager plotted to take him for all he was worth. The two were romantically linked and wanted to drug Whittaker and rob him. Another instance lost him $200,000 to people who just wanted to take advantage of him.
Brandi become super dependent on the drugs she was abusing. She was spending everything she could on drugs like cocaine, methadone, and oxycodone. She was also supplying substances to the people in her life, like her boyfriend, Jesse.
The two did many drugs together, and she would frequently bankroll his addiction. If their relationship was a pharmacy, she was the prescription pad that would ultimately lead to his demise. Whittaker checked his granddaughter into three different rehab and treatment centers, though nothing seemed to work for her.
Whittaker found himself at the center of many scandals, and one stood out specifically. He spent some time playing at the Caesar’s Hotel and Casino in Atlantic City, New Jersey. He ended up bouncing $1.5 million in bad checks to cover his gambling losses!
Caesar’s Atlantic City sued Whittaker, though he ended up countersuing the hotel right back. He claimed that his losses were meant to be credited back due to a slot machine that he developed. He believed that THEY owed HIM money. It seemed he really couldn’t blame himself.
Brandi’s boyfriend, Jesse, suffered from addiction, much like his girlfriend. The couple briefly broke up, and Jesse returned to his family. The two didn’t take long before they got back together… This would be the end of the young man, who was just 18 years old.
He was found dead of an overdose in an empty house owned by Whittaker in Teays Valley, West Virginia. He was lying face down on a mattress, and coroners determined he died from a lethal combination of oxycodone, methadone, meperidine, and cocaine.
Whittaker’s pride and joy was his granddaughter. He loved her more than anyone in the world. Naturally, Brandi was broken up over the death of her boyfriend. She would find herself meeting a similar fate, but not before sharing something troubling with the most important man in her life.
She told her grandfather, “You really can’t help me. I don’t want help; I just want to keep on taking drugs. That’s all I want.” Those words broke Whittaker, who continued to blame his lottery win for the death of his beloved Brandi. After Jesse died, she went into a spiral that would not be fixed for a while.
Not long after the passing of her boyfriend, Brandi disappeared. She dropped out of high school not long before graduation, took copious amounts of drugs, and was hanging out with whoever she could that would help her get the next buzz. Her grandfather would typically not go a day without her calling, but now, it had been weeks.
She was reported missing with the authorities, and her grandmother, Jewell Whittaker, even went on television to beg her granddaughter to come home. Unfortunately, she was found about 11 days after she was reported missing. She was dead, wrapped in a plastic tarp, and dumped behind a van. She was found with drugs in her system, though her cause of death is “undetermined.” She was found on a friend’s property, and no one has been charged.
Jewell was not a fan of what winning the lottery had done to the couple. Her husband had changed, and she was not going to stick around and see what happened to him. She had often said that she wished he had just ripped up the ticket because nothing good came of it.
She filed for divorce in 2005,. She is described as quiet, religious, and not very outgoing – she felt that she had watched their blessing turn into a plague. They ended their 42-plus years of marriage in a contentious divorce, and there is not much public information available on the matter.
Ginger Whittaker-Bragg, his daughter, passed away after battling cancer for years. She outlived her daughter Brandi by a few years and unfortunately died far too young, at the age of 42. Despite battling an illness, she did everything she could to honor her late daughter’s memory.
Before Brandi’s passing, she worked alongside her mother to form the Brandi Bragg Foundation, aimed at helping troubled youth. Losing her daughter was not Ginger’s first heartache; she and her daughter’s deaths were preceded by her first husband, Gary Wayne Bragg, who died on August 18th, 1991.
Whittaker had spent much of his fortune on new homes, even if many remained empty. While his new wife was at their home in Bland County, Virginia, the house burst into flames. Fortunately, she was able to get out safely. Firefighters declared the scene a total loss the following day.
This was one of the last pieces in a string of terrible luck after becoming the “luckiest” man around, having won a jackpot people could only fantasize about. Whittaker disclosed that the home was not insured, which only adds fuel to the fire!
His life was made rich with money that would end up making him poor in every other aspect. Jack Whittaker’s story has become a cautionary tale, proving that money does not buy happiness. He passed away at age 72 of natural causes. The Ronald Meadows Funeral Parlor in Hinton, West Virginia, confirmed these details.
He nearly went broke after years of struggling with alcohol, robberies, scams, and just about anything that could happen to someone. “I’m only going to be remembered as the lunatic who won the lottery,” Whittaker told the Associated Press in 2007. “I’m not proud of that. I wanted to be remembered as someone who helped a lot of people.”