Famous Lottery Winner Cursed By Winnings

So they say, “you win some, you lose some.” This could not have been any truer for one of the most famous lottery winners ever, especially after going through so much in such a short span of time. From Jackpot to Jack squat, Jack Whittaker fell from grace hard in this terrible tale.

History Maker

Andrew Jackson Whittaker, better known as Jack Whittaker, hit the jackpot in 2002 when he won a whopping, mind blowing $314.9 million in the Powerball multi-state lottery. At the time, it was the largest single-ticket lottery win in the history of the U.S.

The Opposite Effect

However, this life changing moment for Whittaker would be just the start of an incredible roller coaster ride. After winning such a monumental amount of money, you would think that all of your problems would be fixed in a second. But this could not have been further from the truth and in fact, the lottery win caused a lot of problems for the businessman from West Virginia. But how did it all start?


At The Top

Let’s go back and set the scene. It was 2002 and 55-year old Jack Whittaker was an entrepreneur at the top of his game. The president of a contracting firm by the name of Diversified Enterprises Construction, Whittaker seemed to have everything he needed in life going to plan. He had a thriving business, a happy family, and a respected reputation. Nothing could bring this busy man down.


Already Rich

Here was an established businessman who already had an astounding net worth of $17 million USD. For most people, this would be an absolute dream come true to have this kind of money. But for Jack who had built his worth from the very bottom, he wanted more. Much more…


Spur Of The Moment

So one day, when he had some time on his hands, he decided to do something he rarely did – he bought a lottery ticket. Jack parked at a supermarket in Hurricane, West Virginia and tried his luck at the Quick Pick thinking that there was no way he would win. He was only stopping to put gas his car and buy himself a deli sandwich. However, after seeing a whopping $100 million potential jackpot, he decided to spend $100 on tickets for the hell of it.



Amazingly, and to the surprise of everyone in the store, Jack hit all the right numbers, which directly led him to the huge jackpot. That day, it was $314.9 million USD annuity, or $113,386,407 in cash. So Whittaker took the cash option and the rest was history. His net worth had shot through the roof and now he had the potential to invest in things that he never could have imagined. So what would he do with his new found fortune first?


Wise Investment?

One of Jack’s first investments was for his family, starting with thee absolute apple of his eye, his granddaughter Brandi Bragg. In an interview on ABC News, Jack admitted that he gave Brandi $2000 a week, believing her to be “very responsible with her money.” He also said that he gave her four cars. You may be asking yourself, ‘four cars for a 17-year-old?’ Yes, we’re asking exactly the same thing. And this was just the start of the bizarre spending.


Let’s Get Spiritual

But he did give back. As a proud Christian, the lottery winner saw it as his duty to “pay it forward” and contribute to the church. So Whittaker donated 10% of his winnings to religious charities. This included multiple institutions affiliated with the Church of God based in West Virginia. In fact, one of the churches in Hurricane had a multi-million dollar renovation.


Pay It Forward

The charity work didn’t stop there. Whittaker took $14 million out of his winnings and founded the Jack Whittaker Foundation. The main goal of this non-profit organization was to improve the quality of life of families with a low income in his home state of West Virginia. This was mainly done through the distributing food, warm clothing and shelter. It seemed like this was a lottery winner with a heart of gold. But was it worth it?


Giving Back

Then, Whittaker performed a true act of kindness. He felt that it was important to give back to everyone who had led him to this moment of incredible fortune and he felt incredibly blessed. This included the deli manager who served him his sandwich at the store that he bought the winning ticket in. As a token of appreciation, Jack purchased a house worth $123,000 for the lady, as well as a Jeep Grand Cherokee. He even gave her a further $44,000. But would his luck run out?


A Turn In Fortune

It did not take long before trouble was headed in his direction. Less than a year after winning the lottery, Whittaker left his car parked in the parking lot of a strip club in Cross Lanes, West Virginia. But then, he received a rude awakening when thieves broke into his vehicle and took a suitcase that had $545,000 in cash. You might be thinking why on earth he would’ve carried that much money in his car. His simple answer was, “because I can.”


Saga Continues

“I’m simply a businessman who has seen his share of failures and successes,” Whittaker said. “My personal life is my own and I make no excuses for my actions.” What happened during the incident is that the thieves broke the driver’s side window and took a briefcase and three $100,000 cashier’s checks belonging to Whittaker. According to police “It’s a known fact that Mr. Whittaker does carry a lot of money around with him, because he does frequent not only that club, but several other establishments … and he does gamble,” said Kanawha County Sheriff Dave Tucker.

Drugged And Robbed

Authorities believed the thief had close ties to the Pink Pony strip club. Whittaker told deputies that he was drugged after his return to the Pink Pony.

Wrong Place, Wrong Time

It seemed like the lottery winner was a regular at this strip club. And he probably spent a little too much time there as everyone who worked there seemed to know who he was. Of course everyone wanted a piece of this multi-millionaire had. There was one case where the general manager and the dancers’ manager, who were dating at the time, got into legal trouble. The couple were accused of plotting to spike Whittaker’s drink and steal more of his money.


Lightning Strikes Twice

A year later, Whittaker didn’t seem to learn his lesson. He just couldn’t stay away from that little downtown strip club. On January 25, 2004, more thieves broke into his car for the second time. This time, they were able to snatch $200,000 worth of cash from his vehicle. Luckily for the lottery winner, the thieves were caught and the money was eventually returned to him. But Whittaker was playing a dangerous game and was running out of luck…


Things Got Ugly

For the first time in his life since winning the lottery, Whittaker was struck down by family tragedy. The riches seemed to negatively affect other members of his family and on September 16, 2004, the body of Brandi Bragg’s boyfriend, Jesse Tribble, was found in Jack’s home. After the autopsy, it was confirmed that the 18-year-old, who Brandi knew since grade school, had overdosed after consuming a combination of different pills. Sadly for Jack, this would be just the beginning of something terrible…


Lottery Slaves

From the very start, Tribble’s father was completely apprehensive about the couple’s relationship. “I know first hand she bought things for Jesse. I was really upset about it,” he said. “He came in with a Michael Jordan basketball jersey, which was two hundred or something dollars at Sportsmart. He came walking in here, had on a golden necklace and had on a pair of tennis shoes that were probably 180 bucks.”


The Blame Game

There is no denying what Tribble’s father thought about the events that played out. As far as he was concerned, Brandi and Jack were to blame for the death of his beloved son. “I think Jack was trying to shower her with gifts and love and it was almost as if she was destroying herself with it,” he said. “I’m gonna say this with total conviction – I blame her for my son’s death, and I hold her accountable.”


Downward Spiral

With Jesse gone, Brandi felt a sense of guilt and was devastated that his dad thought that she was to blame. She became depressed and dropped out of school. Of course, Jack was distraught to see Brandi likr this. “She said one time, ‘Papa, all I care about is [illicit substances].’ It broke my heart,” he said. “We did everything that we thought was humanly possible to keep her away from the [dealers].” Jack also checked Brandi into three rehabilitation programs. But it would not help.



Then, less than three months later, Brandi was reported missing. Jack and his wife Jule  worked tirelessly to find her. They released a statement on national TV. “Brandi, please come home,” she said. “We need you here with us at Christmas time. We need you in our lives, honey. You’re so dear and precious. Please come home.” Jack was hopeful and was even in touch with Brandi on the phone.


Absolute Tragedy

But after a search that lasted 11 days, Brandi was found dead at one of her friend’s apartments. In the most terrible of circumstances, she was found wrapped in a plastic bag, laying behind a van. Unfortunately, Jack and his family would never get full closure as no one would be charged with murder. Also, the cause of her death was unclear. Despite the millions, Whittaker’s life was turned upside down overnight. No money was going to bring Brandi back.


Autopsy Confirms

His beloved Brandi meant so much to him. She was just 15 years old when Whittaker won the lottery. By 17, she was dead, her body found wrapped in tarp behind a junked van. The autopsy revealed recent cocaine use was in her system. The money used to by the drugs was from the allowance that Jack was giving her.

World Turned Upside Down

This week’s tragedy “doesn’t seem fair,” said his pastor, the Rev. C.T. Mathews, for whom Whittaker is building a $4 million church on a hilltop here. “Jack is devastated. That girl was the apple of his eye. She was his only grandchild.”

Money Took Brandi

“My granddaughters dead, probably because of the money,” he said. “I know I really had my arms around her and protected her before I won the lottery. And once I won the lottery there wasn’t enough of me to get my arms around everything. To hold it and protect it. She was the shining star in my life. She was what it was all about for me.”


Jack’s Rage

Jack was heart broken by the loss of his beloved granddaughter, she was his world. This was evident when, in light of his DUI case, which had started in January 2003, Jack snapped at a local law enforcer. He was so angry by the law’s attention towards him but that they never managed to find the culprits responsible for Brandi’s death. “Go after whoever killed my granddaughter,” the lottery winner said. He followed by saying that the authorities, “are trying to convict me of something I didn’t do.”


Caesar’s Court

This was not the end, and along came more legal troubles. This time, the lottery winner had an altercation with Caesars Atlantic City. After accumulating a hefty sum of gambling losses, Jack tried to pay the $1.5 million he owed the casino. However, the checks bounced and they sued him. But Whittaker wasn’t going down without a fight, and also sued Caesars, claiming that the slot machine he founded for the casino should have covered the losses. In fact, he accused Caesars of owing him money.


Grand Theft Fortune

Whittaker still mourned for his granddaughter’s loss two years later, and yet he faced even more legal trouble. On September 11, 2006, a group of people stole all of his remaining fortunes. The thieves in question reportedly cashed 12 checks at 12 different branches of City National Bank. Just a week before this incident, Jack was in trouble for not paying a woman who had sued him. It seemed like Jack was unable to avoid either end of the law. He was constantly either the victim or the culprit.


Neverending Curse

Jack thought that things couldn’t get any worse,  but yet again tragedy struck and reared its ugly head. On July 5, 2009. Ginger Whittaker Bragg was found dead. She was Jack’s daughter and also the mother of Brandi. It has never been confirmed what the cause of her death was. But one thing is for sure, this lottery winner was living under a curse that didn’t seem to be going away. And Jack was losing everyone who he held close to his heart.


The Great Fire

It wasn’t just people that Jack lost along the way. On December 2, 2016, Whittaker’s Virginia home caught fire. Although firefighters quickly arrived on the scene, it was already too late. The house was completely destroyed and to make matters even worse, it was not insured.  Although Jack’s wife was in the house when it caught ablaze, she quickly made it out to safety. Fortunately, the fire didn’t claim any lives.


Fire Fire Everywhere

The fire did however, burn the whole house down, it was considered a write off and a lot of money that was stashed in the house, was burnt to tiny cinders, with nothing left but ashes, just like his life. Everything around him was crumbling, and he now had no money, no home, no daughter or grand-daughter and his wife was ready to leave him. What had he done to deserve this he thought to himself. How would he ever get through this tragedy?

A Lotto Regret

After losing his granddaughter Brandi and his daughter Ginger, Jack was overwhelmed with regret after winning the lottery just a few years beforehand. He firmly believed that winning all that money was the catalyst for all the pain that came his way. “You know, my wife said she wishes she’d torn the ticket up,” he said. “Well, I wish I would’ve torn the ticket up too.” Jack believed that if he could turn back time, he would’ve done things differently.


A Hard Heart

Looking back on all the pain and suffering he has experienced, Jack knows that the experience has fundamentally changed him. “I pretty much lost everything I held dear in my life,” he said. “I don’t like the hard heart I’ve got. I just don’t like what I’ve become.” This harsh reality and series of horrible events deeply impacted Jack’s attitude to life and his belief in religion.


Life Lessons

Since winning the lottery, Jack has learnt some valuable lessons. It has also enhanced his outlook on the world. “Money has never meant anything to me,” he said. “You have to have money to exist in this world. But money doesn’t rule the world. Money is not what makes people happy. Family is what is dear.”  He has been trying to turn his life around ever since and really focus on what matters to him most.

West Virginia Lottery winner Andrew "Jack" Whittaker talks with members of the media about winning $314.9 Million dollards in the Power Ball Jackpot drawing Christmas night at lottery headquarters in Charlston, West Virginia, December 26, 2002. Photo by John Sommers II

What Now?

Jack spends his spare time now giving back to society, as his way of righting all of his wrong doings. He believes that by volunteering and doing what he can for the church, this will let the memory of his daughter and grand daughter live on in a positive way. As for money, he had to go back to square one and start again from the bottom.

Good Intentions

Whittaker bought that ticket for $1 at the convenience store. He had won the biggest undivided lottery pot in American history. When Whittaker flew to New York City for TV appearances a few days later, he brought Brandi came along. She had blond hair, hazel eyes and the same big smile as Grandpa. “This little girl means the world to me,” Whittaker said. When Brandi said she was afraid of flying, Whittaker replied, “I’ll hold your hand.” Whittaker said he didn’t want or need the money himself but was looking forward to seeing it enjoyed by his wife, daughter and granddaughter. It is so sad that he really had a good heart and good intentions at the beginning of his endeavors.


Let’s reflect on the good things he did do with his money. He formed a foundation that launched a campaign to eventually feed and clothe poor people in each of West Virginia’s 55 counties. He also gave a total of $7 million to three preachers and began to build two churches. Whittaker has given about $20 million to charity, according to his lawyer.

Biggest Lottery Winner In Us History

Jack Whittaker is the biggest lottery winner in U.S history. But after this long, and mind blowing reversal of fortune, few of his neighbors would call him lucky. It just shows, that it is so easy to think that if you win a lot of money, that all your problems are solved, yet this story proved the total opposite. A lesson for us all.