Winning Big
Jack Whittaker became a millionaire overnight as he scooped a $314.9 million jackpot in the Powerball back in 2002. It was a multi-state competition, and the biggest win ever at the time.
Winning Big
A Rollercoaster Ride Of Emotions
It is the dream for just about anybody, to win hundreds of millions of dollars on the lotto. The money that Whittaker, of West Virginia, won would open any doors that he wanted. With so much cash, debt was no longer something Whittaker or his family had to worry about again, they were loaded.
A Rollercoaster Ride Of Emotions
Butterfly Effect
The butterfly effect is the idea of changing one thing in the past, and it then completely changing the course of history. Well, Whittaker didn’t have a time machine, but his future was definitely going to change now that he had won so much money. But why would he regret not tearing up his ticket?
Butterfly Effect
Life Was Good
Before Whittaker even won the cash his life was going pretty well. In 2002 he was 55 years old and the president of Diversified Enterprises Construction, a construction company. He was riding high on life, but some extra cash was always going to be welcome, even if he already had everything in life he wanted.
Life Was Good
Big Net Worth
Whittaker wasn’t in charge of a small company; he was already worth $17 million before winning the jackpot. The businessman always wanted more from life, and with the $314.9 million winnings, the world was his oyster. How could this all go so terribly wrong for a man so in control of his life?
Big Net Worth
Feeling Lucky
Whittaker must have been feeling lucky when he decided to play the lottery, something he rarely did. He was just buying gas and a sandwich when he got the temptation to buy a ticket. That decision changed his life forever as he saw there was a $100 million jackpot, so bought $100 worth of tickets.
Feeling Lucky
Taking The Cash
The businessman picked the right numbers and won $314.9 million in annuity, or he could take the cash option of $113.3 million. Whittaker took the cash option and his net worth skyrocketed. With endless possibilities, what was the first thing Whittaker planned to do with his new fortune?
Taking The Cash
Looking After Family
What is the first thing you’d do if you won the lottery? Whittaker wanted to look after his family, so one of his first investments was in his 17-year-old granddaughter, Brandi Bragg. He thought she was responsible with her money so gave her $2,000 per week and four cars. Yep, four cars.
Looking After Family
Looking Out For Others
As a proud Christian, Whittaker wanted to make sure his local church was given some of his funds too. He even donated 10 percent of his winnings to religious charities, seeing it as his duty to look after the fortunes of others. Whittaker’s donations even helped a multi-million dollar renovation for one church.
Looking Out For Others
The Jack Whittaker Foundation
In total Whittaker gave up $14 million of his winnings. He also created the Jack Whittaker Foundation, aimed at helping low-income families in West Virginia. Whittaker helped others by distributing food, shelter, and clothing, and it seemed as though this lotto winner didn’t have a selfish bone in his body.
The Jack Whittaker Foundation
Helping Those Who Helped Him
Whittaker felt as though it was his duty to help everyone who helped him along the way during his life. He even gave the deli manager, who made his beloved sandwiches, a helping hand. Whittaker bought the deli manager a new house, a Jeep Grand Cherokee, and then handed over $44,000.
Helping Those Who Helped
Taking A Turn For The Worse
Despite his good actions, bad things began happening to Whittaker. He left his car outside an adult dancing club with a briefcase filled with over $500,000 in cash. Thieves smashed into his car and took the briefcase. It was a lot of cash to carry around, but Whittaker did it just because he could.
Taking A Turn For The Worse
Finding A Home
Whittaker seemed to like it down at the dancing club, and he was beginning to spend a lot of his time there. People began to take notice, and the general manager was accused of plotting to spike Whittaker’s drink to take some of his cash. Whittaker was becoming a target for criminals.
Finding A Home
Wanting What He’s Got
It seemed as though Whittaker didn’t learn his lesson after being robbed the first time. Once again, thieves broke into his car and stole a briefcase filled with cash, this time they made off with $200,000. Eventually, the thieves were caught and the money was returned to Whittaker… This time.
Wanting What He’s Got
A Downward Spiral
Things would not get any better for Whittaker, and in 2004 the body of Brandi’s boyfriend, Jesse Tribble, was found in his home. The 18-year-old man was confirmed to have suffered from an overdose of narcotics. This terrible incident would only be the beginning of a long and hard road for Whittaker.
A Downward Spiral
Disapproving Father
Jesse Tribble’s father did not approve of the free-spending ways of Brandi. He was upset whenever Whittaker’s granddaughter would buy things for his son, including an expensive Michael Jordan basketball jersey. The money made Tribble’s father completely apprehensive of the entire situation, and the perceived power Brandi had over Jesse.
Disapproving Father
Blaming Brandi
Jesse’s father blamed Brandi for losing his son. He thought that Whittaker had been showering his granddaughter with gifts and she was destroying herself with it. No parent wants to bury their child, and it seemed as though Jesse’s father was pointing the finger at Brandi and her grandpa for their role in Jesse’s passing.
Blaming Brandi
More Lost Than Ever
Brandi confessed to her grandfather that since Jesse’s passing she was even more lost. Whittaker tried to stop her from contacting the dealers who were giving her the illegal substances and even checked her into three different rehabs. Nothing would work, and it left Whittaker feeling heartbroken because of his granddaughter’s constant suffering.
More Lost Than Ever
Brandi Went Missing
As if Whittaker and his family were not worried enough about Brandi, she went missing three months after Jesse’s passing. Jack and his wife Julie did everything they could to find their precious granddaughter, including making an appeal for her to come home on TV. Jack spoke to Brandi on the phone, but she stayed away.
Brandi Went Missing
Finding Their Granddaughter
After 11 days of searching, Brandi was finally discovered at a friend’s house. She was wrapped in a plastic bag and had sadly passed away. The circumstances surrounding her passing were unclear and whoever was responsible for Brandi losing her life was never discovered. Despite his almost endless supply of cash, Whittaker couldn’t bring Brandi back.
Finding Their Granddaughter
Jack’s Shining Star
Whittaker admitted that before winning the lotto he was always there for Brandi, but once the money came along he was distracted. He says her passing is “probably because of the money” and makes a trip to visit her grave every week. Whittaker said Brandi was the “shining star in his life.”
Jack’s Shining Star
Unwanted Attention
Whittaker was receiving a lot of attention from the police, and he lost it with one of the officers. The loss of his granddaughter had left him shaken, and he was angry at the law’s failure to discover who had caused Brandi to be taken so soon. He also thought the police were wrongly pursuing him.
Unwanted Attention
Gambling Debts
Whittaker wasn’t just having troubles with the law. He racked up serious gambling debts, and Caesars Atlantic City wanted him to cough up what he owed them. Whittaker had run up debts with the gambling establishment of $1.5 million, and they had no more patience. It was time to pay.
Gambling Debts
No, You Owe Me Money
Although Caesars claimed Whittaker owed them money, he was convinced they were wrong. Whittaker had provided them with a slot machine and claimed that that should have been more than enough to pay his debt. The casino sued Whittaker, and he sued them right back. It was a very sticky situation to be in.
No, You Owe Me Money
More Financial Woes
By September 2006 Whittaker found himself in hot water once again. This time a group of 12 people came along and wiped out his entire fortune. One week before he was robbed, Whittaker was in trouble for not paying a woman who had tried to sue him. Trouble seemed to follow Whittaker wherever he went.
More Financial Woes
Another Family Tragedy
In 2009 there was yet more tragedy, and Whitaker had to say goodbye to his daughter Ginger Whittaker Bragg. She passed away, but there was never a confirmation about how it happened. The only thing that Whittaker knew for sure was this money had been nothing but a curse for him and his family.
Another Family Tragedy
Recent Troubles
Whittaker has yet to be freed of the curse, and in 2016 his house caught fire. Despite the best efforts of the local fire department, Whittaker’s home could not be saved, and everything was destroyed. Luckily the fire didn’t claim the lives of any more of Whittaker’s family, but the damage had already been done.
Recent Troubles
Turning Back Time
The losses of both his daughter and granddaughter hit Whittaker hard, and he believes winning the money was the reason for their passing. He regrets winning the cash and wishes he could go back in time. Whittaker believes he would tear up the winning ticket if he could go back.
Turning Back Time
Losing Everything
Whittaker says he has “pretty much lost everything he held dear in his life.” He has had to become hard-hearted because of the tragedies and pain he suffered. So many years of misfortune have changed Whittaker, and he is no longer the warm person he once was before the money.
Losing Everything
Family Matters
After losing his close family, Whittaker believes he has learned some harsh lessons in life. He said “family is what is dear” and that “money has never meant anything” to him. Whittaker believes money is essential for people to survive in this world, but family is what makes folks truly happy.
Family Matters
Not The Only Sad Story
It turns out that Jack Whittaker wasn’t the only lotto winner who ended up down on his luck. British winner Michael Carroll scooped $12,858,654 in 2002 when he was just 19 years old. He worked in garbage collection but soon began living out the life he could previously have only fantasized about.
Not The Only Sad Story
Living Life To The Fullest
Carroll made sure he enjoyed every second his lottery winnings brought him. He bought himself a fancy mansion in the British countryside, annoying the neighbors by racing cars in his garden. The young lottery winner also invested money in his favorite soccer team, Glasgow Rangers, and generally lived a lavish lifestyle.
Living Life To The Fullest
Not Seeing The Warning Signs
All of this money was new to Carroll, and it felt as though he had an unlimited amount of cash. There wasn’t a lot of money in his family, so now Carroll was having as much fun as possible. No one could begrudge him having his fun, but he became a villain in the UK.
Not Seeing The Warning Signs
Making Himself An Enemy
The British press were out for blood when it came to Michael Carroll. Here was a man who was enjoying himself so much he didn’t care who he upset, all that mattered was his happiness. He started acting like an overgrown child, and soon reports began to emerge that described some of his bad behavior.
Making Himself An Enemy
Trouble With The Law
Carroll felt invincible and started acting out against society. He took a trip in his Mercedes smashing the windows of shops and cars in his hometown using ball bearings. Carroll was found to have consumed a lot of drink and was forced to stay away from the town or face prison time.
Trouble With The Law
Losing It All
By 2006 Carroll basically lost every cent of the $12.8 million he had won on the lottery. It was a good run for Carroll, but just four years after having riches beyond his wildest dreams he was basically broke. The BBC reported he had lost it all by partying, buying cars, and illegal narcotics.
Losing It All
Coming Full Circle
In 2010 Michael Carroll’s life had come back to where it all began. In 2002 he was working in garbage collection, and in 2010 he applied for his old job back after admitting all of his cash was gone. Despite losing it all, unlike Whittaker, Carroll said he had no regrets about losing his money.
Coming Full Circle
A Record Loss
Another lottery winner, Bud Post had made a fortune by buying himself a ticket. He took home $16.2 million in the Pennsylvania lottery back in 1988, but just one year later he lost it all. In fact, not only had he squandered the entire $16.2 million, he was actually $1 million in debt.
A Record Loss
Wishing It Never Happened
Post admitted that winning the lottery never happened for him as his ex-girlfriend sued him for a third of his winnings. She managed to win her case and almost immediately Post had to kiss goodbye to over $5 million. That was not the worst part about Post’s story however, it would go further downhill.
Wishing It Never Happened
A Hit Was Taken Out
You’re supposed to be able to rely on your family for anything but Bud couldn’t. After Bud won his cash his brother was arrested for reportedly hiring a hitman to take him out. It seemed Bud’s brother thought he would inherit the money with Bud’s passing. Bud claimed he was “happier when I was broke.”
A Hit Was Taken Out
