You know what they say, “you win some, then 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.
Andrew Jackson Whittaker, better known as Jack Whittaker, hit the jackpot in 2002 when he won a staggering $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 monumental moment for Whittaker would be just the start of a roller coaster ride of a life. After winning such a hefty cash prize, you would think that all of your problems would be sorted in the blink of an eye. But this could not have been further from the truth and in fact, the lottery win caused what seemed to be a butterfly effect of problems for the businessman from West Virginia. But how did it all start?
At The Top
Let’s go back to the start of the story and set the scene. It was 2002 and 55-year old Jack Whittaker was an entrepreneur at the peak of his powers. The president of a contracting firm by the name of Diversified Enterprises Construction, Whittaker seemed to have everything he needed in life. This was a man with a thriving business, a happy family, and a respectful reputation. Nothing appeared to be able to bring this busy man down.
To make things even clearer just how settled Whittaker already was, let’s break it down into numbers. Here was an established businessman who already had an incredible net worth of $17 million USD. For most people, this would be an absolute dream come true if they were worth this much. But for someone like Jack who had built his worth from the very bottom, he was on a road that he couldn’t pump the breaks on. He wanted more. Much more…
Spur Of The Moment
So one day, when he had some time on his hands, Whittaker decided to do something he rarely did beforehand – he bought a lottery ticket. Jack parked at a supermarket in Hurricane, West Virginia and tried his luck at the Quick Pick. He was literally just stopping to refill his car with some fuel and buy himself a deli breakfast sandwich. However, after seeing a whopping $100 million potential jackpot, he decided to spend $100 on tickets.
Amazingly, 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 and grow in ways that he never could’ve dreamed of. For Jack, the possibilities were endless. So what would he do with his new found fortune first?
One of Jack’s first investments was for his family, starting with his pride and joy, 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 let’s take a step back and focus on one of the high points of Whittaker’s spending. As a proud Christian, the lottery winner saw it as his duty to “pay it forward” and contribute to the church in some shape or form. 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 the 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 distribution of food, clothing and shelter. It seemed like, on the whole, this was a lottery winner with a heart of gold. But was it worth it?
Then, Whittaker performed the ultimate act of kindness. He felt like it was completely necessary to give back to everyone who had led him to this moment of fortune. 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 was this going one step too far?
A Turn In Fortune
It wouldn’t take long before trouble started coming his way. 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 may be wondering why on earth he would’ve carried that much money in his car. His simple answer was, “because I can.”
Everybody Wanted A Piece
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. As a result, everyone wanted a piece of this multi-millionaire. 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, a couple of 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 came and was running out of luck…
Things Got Ugly
For the first time in his life since winning the lottery, Whittaker was plagued 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 illicit substances. Sadly for Jack, this would be just the beginning of something terrible…
From the very start, Tribble’s father was completely apprehensive about the couple’s relationship, especially after Jack’s lottery triumph. He didn’t like how free they were to spend money. “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 transpired. 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.”
With Jesse out of the picture, Brandi felt more lost than ever. She became depressed and dropped out of school. Of course, Jack was distraught to see Brandi in this situation. “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. And it wasn’t just Jack who was fighting to save her and locate her whereabouts. His wife Jule also worked tirelessly, releasing 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.
But after a search that lasted 11 days, Brandi was found dead at one of her friend’s residences. 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.
Money Took Brandi
Now, Jack makes a haunting, weekly visit to Brandi’s grave. “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.”
Lost and unsure who to turn to, Jack was naturally shaken by the loss of his granddaughter. 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 enraged by the law’s attention towards him but their failure 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.”
Away from Whittaker’s personal life 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
A couple more years passed and Whittaker was in the thick of 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.
Just before Jack thought that things couldn’t get any worse, tragedy once again turned 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. But one silver lining came out of the fire. 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.
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.” As harsh as the reality is, it should be no surprise that so many years of loss and misfortune would have a considerable impact on Jack’s attitude and beliefs.
But there is no denying that the tragedy that has plagued Jack since winning the lottery has taught him some truly 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.” And the fact that Jack is still here to say that is the ultimate triumph.