This lottery winner won more than $314 million but now says he wishes he never bought the ticket

The lottery. Everyone thinks that they want to win it until it actually happens. There have been countless stories of lottery winners losing all of their money or even worse, their friends and family. While many people believe that money is the key to happiness, the stories of these people are proof that money cannot solve every problem. That being said, one cannot deny the importance of money. Money allows us to live by giving us the ability to feed, shelter and clothe ourselves.

Money can also bring families closer as it can allow loved ones to spend time on vacation together and show each other appreciation through gifts. In addition, many divorces are caused due to financial issues and having money can obviously ease some of the financial burdens that couples face. As much as we know that money is not the bearer of happiness, it is a necessary evil that everyone needs to survive.


This is the reason why so many people are after money and go out of their way to get it. Many people turn to a life of crime in order to make money without having to work for it. For those who want to make a lot of money without going to jail for it, the lottery is a great way to have a chance at becoming a millionaire.

Although the odds of winning are extremely low in most cases, many Americans continue to play the lottery in hopes that they will be able to quit their jobs and live a life of luxury. It does not happen frequently, but every so often a lottery winner shows up in the newspaper holding a huge cheque and smiling from ear to ear.

For one West Virginia man, winning the lottery was never his dream but he was still overjoyed when he found out that he was the owner of the winning ticket. Jack Whittaker won a jackpot of almost $315 million, which, at that point was the biggest jackpot ever to be won in the country. What was different about Jack’s lottery win was that he was already millionaire to begin with!

However, the money did have an immense effect on his life, however, the effect was more negative than positive. Through his lottery experience, Jack Whittaker learned the harsh lesson that family is more important than money. Unfortunately, the West Virginia man had to endure unthinkable tragedies in order to learn this lesson.

Making history

Andrew Jackson Whittaker (who goes by Jack) beat all of the odds in 2002 as he discovered that he was the winner of a lottery jackpot of almost $315 million. In the year that he won it was the largest jackpot ever in American history and Jack was the the lucky winner. However, looking back on his big win, Jack does not feel so lucky. Most people could only dream of winning so much money so why does Jack look back on this event as having negative consequences in his life?

More money more problems

What should have been a monumental moment in Whittaker’s life, turned out to be a big event for all of the wrong reasons. It thrust him into a long ride of emotions and made him regret ever purchasing the ticket. While most of us believe that winning a lottery ticket would solve all of the problems in our lives, it turns out that money cannot buy happiness and it can often cause more harm than good.

Business man

In 2002, Jack Whittaker was a successful businessman from the state of West Virginia. He was the president and owner of a contracting company called ‘Diversified Enterprises Construction’. He was successful and had a thriving career and everything seemed to be going great in his life. He was busy and had a good reputation as a businessman and had everything he needed. He could never have imagined how much his life was about to change.

From rich to richer

What makes Jack different from most lottery winners is that he was already a millionaire to begin with. Whittaker had a very successful business and he already had a net worth of seventeen million dollars. He was living a very comfortable lifestyle and most people might think that if they already had they kind of money, they wouldn’t feel the need to buy lottery tickets. However, Jack had made his fortune from nothing and he was after something much bigger.

Last minute ticket

Jack did not purchase lottery tickets on a regular basis but on one fateful day he decided to do something out of the ordinary and buy a ticket. Whittaker was the in the small and oddly named town of Hurricane, West Virginia when he walked into a supermarket and picked up a Quick Pick ticket on his way out. He was simply stopping to buy a deli sandwich and refuel his car but when he saw that the potential jackpot was $100 million, he bought $100 worth of tickets.

Against all odds

Although Jack bought multiple lottery tickets, the odds were still against him. With such a high jackpot at stake, more people than usual were buying tickets so there was less of a chance for him to win. The jackpot that Whittaker now had in his possession was nearly $315 million. He had the option of getting it paid out in monthly installments or taking a lump sum of over $113 million. His net worth skyrocketed within an instant and he was given the opportunity to grow his business in a way he could never have imagined.


Most lotteries have an option for the winners to remain anonymous, but the vast majority of people seek the fame that their fortune brings them. They will immediately start buying fancy clothes, expensive cars, and start giving money to friends. However, this may lead to the wrong kind of attention. Organized crime syndicates love to extort lottery winners. It is also a well known phenomenon that friends and family may also try to extort you for some cash.

Questionable investments

Although many thought that Jack would invest his fortune or put it in the bank, he chose to invest in his granddaughter named Brandi Bragg. Jack admitted in an interview with ABC news that he was giving his granddaughter an allowance of $2000 per week. He claimed that she was being, “very responsible with her money” but the public was concerned about his spending as he also gave her 4 cars. These presents seemed odd as Brandi was only 17 years-old at the time.

Giving back

Although Jack was making some odd spending choices, he also donated a large portion of his winnings to his local community. Jack, a religious Christian, donated 10% of his millions to various religious charities. He felt that it was his duty now that he had so much money. Many of the charities that received donations from Jack were associated with his church in West Virginia. He even gave the Church of God millions of dollars, which they used to renovate the building.

Foundation donation

Whittaker continued to be generous with his earnings and even started his own charity with 14 million dollars. It was called the ‘Jack Whittaker Foundation’ and the main goal of the charity was to improve the living situation of families living in poverty in West Virginia. They did this through giving people shelter, clothing and food. It seemed that Jack was being extremely generous with his winnings but did he think it was worth it?

Going overboard

Jack was being generous with his millions but was he being too generous? He felt that he needed to return the favor to every person that had helped him earn his fortune including the supermarket owner who sold him the ticket. Jack went above and beyond to give back to the owner by gifting her a Jeep and a house that was worth more than $120,000. He did not stop there, He gave her an additional $44,000! But had he gone too far?

What to do?

After winning so much money in such a small amount of time, most people are at a loss of what to do and they start spending without stopping. Instead, the smartest thing you can do is get a lawyer as well as a financial planner to make sure that you do not spend all your money in one go. They will help you to make wise choices with your money, protect your new windfall, and perhaps even invest it to get you even more money!

A change of luck

Up until this point, Jack was living a happy life with his newfound fortune but he could never have expected his luck would change and troubles were around the corner. Not even a year after Jack won the lottery, he parked his car next to a gentleman’s club in West Virginia. Jack had left a suitcase filled with over $540,000 in his car but it was stolen when robbers broke in. Many people were stunned that Jack had so much money on him and when asked why he did it, he simply responded, “Because I can.”

Plots against him

When this story broke, it was discovered that Whittaker was a frequent patron of the gentleman’s club. All of the employees there knew who he was and they new that he was a millionaire. They all wanted a piece of his fortune and there was even an alleged plot against him. One of the dancers at the club was dating her manager and the two were accused of reportedly planning to spike Jack’s drink in order to steal his money off of him.

Lessons not learned

Although Whittaker should have known better than to go back to the club, he did not learn his lesson and as a result, history repeated itself. This time, Whittaker had left $200,000 in his car, which was inevitably stolen when he took a trip to the gentleman’s club. However, Jack got lucky this time and the police were able to recover the stolen cash. However, Whittaker was about the run into a lot more bad luck.

Family tragedy

Losing money is one thing but losing a loved one is a whole different story. Since his lottery win, Jack had run into financial troubles but his family was about to experience a major loss. In 2004, Jesse Tribble, Brandi Bragg’s boyfriend, was found dead in Jack’s home. It was later confirmed that Jack, who was 18, had died after he took illicit substances. This was a devastating loss for Brandi and it was the beginning of bigger troubles for Jack.

Buying love

When Tribble’s father heard the news of his son’s death he was understandably heartbroken and explained that he was never happy about Jesse dating Brandi. He knew that Brandi was using her grandfather’s money to buy Jesse items and Jesse’s father was upset about it. He said that his son began coming home with new, flashy items such as basketball jerseys and a gold necklace. He stated that, “had on a pair of tennis shoes that were probably 180 bucks.”

Who is to blame?

If Jesse’s untimely death was not enough, things were about to get even more dramatic in the Whittaker’s life as Jesse’s father blamed Jack and Brandi for the death of his beloved son. “I think Jack was trying to shower her with gifts and love” he continued. Jesse’s dad put full responsibility on Jack and Brandi for his son’s death and blamed them and them alone. This was a shock for Brandi to hear and it greatly affected the teenager’s life.

Heading downhill

The loss of her boyfriend turned Brandi’s life upside down and left her feeling completely lost. She dropped out of high school due to depression and Jack became distraught at what was happening to his granddaughter. Jack claimed that his heart was broken when Brandi came to him and said that all she cared about in life was illegal substances. Jack tried to keep her away from a life of crime and even sent Brandi to multiple rehab programs but to no avail.

Brandi went missing

Only three months after Jesse passed away, Brandi went missing. Jack and his family worked tirelessly to locate her and they even put out a statement on national television. His wife made a statement on the news saying, “Brandi, please come home. “We need you here with us at Christmas time.” She went onto say that Brandi was so important to their family and that she should come home. The family was hopeful that Brandi would return and Jack was even able to get in touch with her over the phone.

Tragedy strikes again

The search to find Brandi continued for 11 days and ended when she was found dead in a house where her friend lived. Brandi’s body was discovered behind a van and she was in a plastic bag. Even worse, Jack and his family never received closure as Brandi’s killer was never brought to justice. The Whittakers has gone through so many traumatic events and their lives were turned upside down. All the money in the world could not bring Jack’s granddaughter back.

Blaming the lottery

Jack believes that Brandi died because of the money she was given. He stated, “My granddaughters dead, probably because of the money.” He went onto say that before he won the lottery, he was able to protect her but due to her access to large amounts of money, he was not able to get control of everything that she was doing. Brandi was the light of Jack’s life and he could not imagine living without her. He now makes a weekly visiting to her resting place.

Seeking justice

Jack was absolutely devastated at the unexpected loss of his granddaughter. He wanted her killer to be caught and punished, which led him to lash out at a local police officer. Law enforcement was paying more attention to Jack’s DUI case that had started in 2003 and he felt they should be focusing on Brandi’s death. He stated, “Go after whoever killed my granddaughter.” The lottery winner continued by telling the police that they were trying to convict him of something that he claims he never did.

Gambling problems

On top of Whittaker’s personal struggles and legal battles, he also got involved in a fight with Caesars hotel in Atlantic City. Jack had gambled much of his money away at the casino and he owed them around $1.5 million. When the cheques that Jack gave the casino bounced, they filed a lawsuit against him. However, Whittaker retaliated and countersued Caesars and claimed that the losses should have been covered by the slot machine he had given them.

Stolen fortune

As the years went on, Jack was losing more of his money and getting into more trouble. In 2006, the remainder of his money was stolen and the thieves reportedly cashed in twelve cheques at twelve separate bank branches. One week prior to this incident, Jack got in legal trouble for refusing to pay a woman who won a lawsuit against him. Jack was not able to run away from his legal troubles and he was on both sides of the law as both the culprit and the victim.

The curse of the lottery

It seemed that Jack’s life could not get any worse but as it turns out, it did. The Whittaker family faced another huge loss when Brandi’s mother, Ginger Whittaker Bragg, was discovered dead in July of 2009. Until today, the cause of her death has never been confirmed but it seems that Jack and his family had a curse on their heads. Jack was losing everything that mattered to him and his life was spiraling downhill.

House fire

Jack had lost family members and his fortune, but in 2016 he lost his all of possessions. Whittaker’s home caught fire and by the time firefighters arrived on the scene, everything was already destroyed. His house and all of his possessions inside were burned and it that was not bad enough, Jack had not insured his home. There was one silver lining, however, as neither Jack or his wife were injured in the blaze.

Regretting everything

Jack had lost his daughter, his granddaughter and his fortune over the course of a decade. His losses were so great that he regretted ever buying the lottery ticket in the first place. He was certain that the money was the reason for all of his problems. Jack stated, “You know, my wife said she wishes she’d torn the ticket up.” Jack went onto say that he wishes he would have torn it up too. He wished that he could have gone back in time and stayed far away from the supermarket where he purchased the ticket.

A heavy heart

Looking back on the last decade of his life, Jack realizes that the fact that he won the lottery was a big contributing factor to his heartbreaking situation. “I pretty much lost everything I held dear in my life,” he stated.” In addition, Jack realized that they lottery changed him as a person and he said, “I just don’t like what I’ve become.” Jack has realized that reality is harsh and his many losses over the years have shaped his worldview.

Money isn’t everything

It is impossible to ignore the tragedy that Jack’s lottery win has brought upon his life. While Jack was once excited about his future with his millions, he now wishes he never won the lottery. He never believed that money was important in his life and that, “Money is not what makes people happy. Family is what is dear.” Unfortunately, Jack had to learn this lesson for himself. Jack cannot bring his family back and is devastated that all of this occurred due to his lottery win.

Most important strategy

Lots of people claim to have different strategies when they are playing the lottery or a scratch off game, but there is one thing that they all agree on – have a budget and stick to it. If you have just bought your original lottery budget’s worth of tickets, you should stop. Buying one more will not greatly impact your chances of winning, and it is not worth breaking the bank for it. It is better to walk out and keep the rest of your money.


This is the part that makes sure that the lottery ticket that you have is yours. You HAVE TO SIGN THE TICKET. If you do not put your signature on the ticket then anyone can come in and claim that it is their ticket and that you stole it. Even if what they are saying is a lie, you won’t be able to prove it until after a lengthy and expensive court case. Money does strange things to people, and you never know who will try to steal from you.

Why it happens

There is such a small chance of winning the lottery that it is hard for people who do not play to understand what the big draw is. That is why so many psychologists have decided to research the phenomenon, and what they discovered is actually pretty predictable. It turns out that those who play the lottery are tricking themselves into thinking that they have enough luck to win, and because of that, they think that they have a higher chance of winning.