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Jack Whittaker: A Victim of the Lottery Curse?

Let’s be honest: Most of us have fantasized about winning the lottery. Surely all that wealth would transform our lives for the better, even if it failed to make us significantly happier? The fact is, for many lottery winners the only outcome is pain and tragedy – hence the supposed “lottery curse.”

The lottery curse has claimed many a victim. So strange and haunting are some of their stories that even the most rational person cannot help but wonder if the winning ticket really is jinxed. Consider, for example, the sad tale of Jack Whittaker.


On December 24, 2002, Whittaker, then aged 55, stopped at a convenience store in the town of Hurricane, West Virginia, to purchase fuel for his vehicle, a couple of sandwiches, and a $1 Powerball lottery ticket. A multimillionaire – he owned a successful contracting firm that employed over 100 people – his decision to purchase the lottery ticked was hardly motivated by financial desperation. When the Powerball results appeared on television that evening, Whittaker was disappointed to hear that he’d lost by one digit. The following day – Christmas – he practically fainted when he heard that the results had been broadcast incorrectly, so that his was in fact the winning ticket.

A day or so later, Whittaker – accompanied by his wife Jewel, his daughter Ginger Whittaker Bragg, and his 15-year-old granddaughter Brandi Bragg (Ginger’s daughter) – was photographed holding a giant cheque for the sum of $314.9 million, a record breaking win at the time. Whittaker had two choices: to receive the money in annual installments over a period of 29 years, or two accept a onetime payout of approximately $113 million. He chose the latter option, ending up, after tax, with around $93 million – still a huge sum, though only a fraction of what he’d been announced as winning. Even from the start, there was something not quite right about the money. “I’ve had to work for everything in my life,” he reflected. “This is the first thing that’s ever been given to me.”

Whittaker gave tens of millions to charity, even setting up a foundation to provide food and clothing for the needy of West Virginia. A dedicated Christian, he also donated a portion of his winnings to the church. Less than a year later, however, things began to turn sour for the man with too much money. In August 2003, during a visit to a strip joint called the Pink Pony, he was robbed more than $500,000 in cash and cashier’s checks, the money and checks stolen from his Hummer parked outside. Several months later, he was arrested after driving his Hummer into a concrete median, the arresting officer claiming that he smelled alcohol on Whittaker’s breath.


No matter how much he tried to enjoy his enormous wealth, Whittaker couldn’t help but attract bad luck. More of his money was stolen by thieves; one woman tried to sue him for sexual assault; he was arrested for further drink driving incidents; he and his wife separated after more than forty years of marriage; the list of misfortunes goes on.

But if Whittaker had become a target for bad luck, so had his family members and acquaintances. In September 2004, Brandi Bragg’s boyfriend, Jessie Joe Tribble, 18, was found dead in Whittaker’s home. He had died of a drug overdose. That December Bragg went missing. A few weeks later her heavily decayed body was found wrapped in a plastic tarp behind a dilapidated truck, her death the result of an accidental overdose. Whittaker – who had basically raised Bragg himself and considered her “the shining star of my life” – was understandably devastated. “I wish I’d torn that ticket up,” he told reporters at the time.

In keeping with the adage “bad luck comes in threes,” Whittaker’s daughter Ginger, 42, was found dead in her luxury home in July 2009. Although foul play was never suspected, the exact cause of her death remains unknown.

Sadly, Whittaker’s troubles haven’t ended; reports have surfaced suggesting that he’s broke.

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  • I don`t believe in “bad luck” but I`ll tell you this, – if I won such an amount of money I`d keep it very secret. Too many jealous people would make your “bad luck” for you.

  • Lyon25

    This doesn’t sound like a curse. $500k in your vehicle outside the strip club? Multiple drunk driving arrests? Not a curse; it’s stupidity.

  • Mar Iséll

    I wonder if it has to do with people not educated and knowing what to do with such a large sum of money in their possession and how to be financial responsible. For example, leaving cash in his vehicle. Also being known by the public as one of the largest lottery winners at the time – which made him a target by unscrupulous people.

  • Candiruphobe

    Keep it as secret as possible + move away.

  • Jim

    Indeed. Winning this much money is a great responsibility, and the biggest is to live your life with a little intelligence and caution. Sounds like the whole family was lacking those qualities.

  • Aimee

    Strip clubs? Sexual harassment? He drove a Hummer and carried 500k to that aforementioned strip club? Maybe this isn’t a case of a lotto curse, but in fact a douche bag getting what was coming to him?

  • sal paradise

    I don’t think Lotto Jack is broke. His original business has been hurt a bit by the recession and lawsuits (he seems to have been sued continuously since he won, especially by his ex wife and organizing unions) but doing ok. He has invested heavily, in fact some say he ‘shot his wad’, buying various operations from racing tracks, to restaurants, to payday loan joints to used car lots (he finances). No bankruptcy filings have been made in his name either, which suggests his being out of cash isn’t true. If anything, Lotto Jack’s luck with business is holding true and he’s more than likely raking it in.
    Locals in his hometown say he still gets around town, but not as much. The deaths and his divorce, plus old age and health concerns have slowed him down somewhat. He still runs his business operations but is not as active in his original company.
    Lotto Jack has had some bad breaks. He’s lost family, drove stone drunk and has grabbed and chased women in topless joints, bars, casinos, you name it. But all of that was years ago. I imagine he’s had his fill of the fast lane.
    However, he is still way ahead of fellow winner from down the road, David Edwards. Edwards took home $27,000,000 in 2001. By 2005 he was broke and a year later was living, with his wife, in a storage garage in Florida (where else you can wonder). Edwards lifetime of drug abuse finally got the better of him and he was rushed home to Ashville, Kentucky near death from a hepatitis infection. Although rumored to be Edwards is not currently dead and is probably living in the Ashville area, where he is from. Unlike Lotto Jack, Edwards seemed to thrive in bringing attention on himself, appearing on lottery winner cable programs at least twice, and often in local media doing interviews about donations and other ventures.
    Edwards story is sad. He literally lost everything he won in the lottery. That must be a real bummer. He must be having constant reverse lottery dreams, this time dreaming of actually spending his winnings less and following advise from his financial people. No matter how much you say something like ‘it was a great ride’ losing the money still has to sting a bit.
    Mr. Edwards health has been said to be pretty bad. Back in 2007 his world came down on him. Kicked out of his storage house for non payment, his expensive mansion repossessed, his hepatitis and his wife strung out from serious drug addiction and with warrants for he arrest for failing to make child support payments, Edwards was probably glad to get the heck out of the great state of Florida and go back to the east Kentucky hill country. Broke but still alive.
    Lotto Jack is on easy street compared to Edwards. Financially at least from all accounts known to the public. Neither is a sympathetic character to the public, especially Edwards and his story. Edwards had promised at his winners press conference that he would be wise with his money and save for the future. He would not let the cash change him. That he would never forget where he came from. You can have fun with those points until your fingers get tired on the keyboard. Bottom line is that Edwards violated everything he said he wouldn’t. Lotto Jack at least stuck to his word and donated an awful pile of cash to help the needy. He eventually was overwhelmed by the negative forces out there who demanded he pay them for whatever ailments they had. They all wanted his money. Nothing he did seemed to please any of those evil frauds and fakes who took him for an easy mark.
    Edwards donated a few bucks here and there. One report estimated he gave out about $50,000 total. Most of it to a boys club back home. Lotto Jack had much more to give but still left Edwards in the dust. Edwards literally blew his dough: on Vegas weekends, on airplanes, on bogus telecomm businesses, on many cars, on a big house in Florida (and another one in Palm Springs, CA) not to mention on mass quantities of drugs, enough to make Elvis blush. Plus several rehabs for the wife.
    Let’s hope both Lotto Jack and Edwards make it past the hard times they have known and pass on to the other side to have a happy life. They’ve served their time, both of them reacting poorly to their winnings. They paid the price for that. Maybe now they can move on.

  • David

    I read another article where a psychologist commented that when you suddenly gain financial wealth without counselling for your new fortune – then it is very possible for whatever self control you have for such things as drinking, drugs, etc. to become extremely difficult to remain in control of. For example, If you like to have a drink “every once in a while”, then, with loads of money, every once in a while easily becomes “all the time”. This is most likely what happened to this individual.

  • 18235

    better to have a lousy life of a millionaire than the good life of a pauper.

  • What the hell? You keep tabs on the mans life? What business is it of yours? Oh, that’s right, none.
    You’re probably one of them leeches that want some. You freak.

  • J.Griffin

    You obviously live a blind,sheltered life.

  • It_is_I

    Sounds like the “curse” is alcohol, not his winning the jackpot. Although I have known (personally) at least one million-dollar jackpot winner and it did cause more problems than joys, as far as I could see.

  • NBAFan123

    ““I wish I’d torn that ticket up,” he told reporters at the time.” – He still spends $2400 a month on lottery tickets. I guess his love for money did not decrease even with humongous amounts of money on hand…