Oh, sure. Winning one billion dollars would be nice.

Actually, it would be totally sweet.

BUT - it could also be the worst thing that ever happened to you.

Case in point: Jack Whittaker.

Getty Images
Getty Images

Jack was 55 years old when he scored one of the largest jackpots in American history, $315 million. When he won, he confidently announced that he planned to live as if nothing had changed.

And, by all accounts, Jack should have been able to do just that.

Thanks to growing a successful business most of his life, Mr. Whittaker was already worth $15 million when he won. This was a guy that knew how to handle wealth. He was certainly no slouch in the managing-of-money department.

Jack took the all-cash option. Practically everyone recognizes this as the smart thing to do. He immediately took possession of $114 million in cash, after $56 million in taxes.

Perfect. He was off to a great start.

But then everything went to Hell.

Whittaker quickly became the target of financial stalkers. Every morning for years, Jack had frequented a small diner in his West Virginia hometown for breakfast. Now, that was impossible.

Each day he was greeted by a mob of people whose daughters had cancer or desperately needed dialysis. Some of them had sure-fire business plans and Power Point presentations. Many didn't even have a story. They just needed a small loan of $500.

When Jack stopped going to the diner, he was branded as cold, heartless and stingy.

But Whittaker wasn't. At all. He tried to do the right thing.

He hired people to sort his mail and a couple of detectives to filter out the con men.

Jack gave to those he felt truly needed his assistance.

A devout Christian, Mr. Whittaker donated 10% of his winnings to churches in southern West Virginia. One of them built a new, multi-million dollar facility thanks to him.

He also shared his winnings with the woman who had sold him the ticket. He gave her $40,000 and bought her a house.  But his generosity only made her a target. She too was stalked and hounded by those looking for a hand out.

Jack offered his city a lump sum of $10,000 in an effort to make the local water park handicap accessible, but that wasn't enough. The press accused him of spending more than that at the local strip club.

Amusingly, this was true.

Whittaker's car was broken into on a number of occasions by trusted acquaintances, all looking for rumored large-sums of cash that he might keep in the glove box.

He couldn't go out anymore. The last time he stopped by his favorite watering hole, someone roofied him.

But, he soldiered on.

Jack reinvested in his business. He tripled the number of people he employed, making him the largest employer in his corner of West Virginia.

Whittaker set up a foundation, eventually handing out more than $14 million to charitable organizations and helping to feed, clothe and house the homeless.

Of course, he took care of his family too.

But, once again, Jack's generosity backfired. His kin were thrust into an odds-defying round of overdoses, emergency room visits and even fatalities.

His granddaughter Brandi, for example, was found dead after having been missing for several weeks. Jack had given her a $2,100 a week allowance and her official cause of death was an O.D. Whittaker cried foul play, however, as her body had been found wrapped in a tarp in the back of a rusted out van.

Nobody seemed to listen. Not even the cops. In fact, Jack was routinely pulled over and ticketed for minor violations (failing to use his turn signal, maladjusted headlights). Despite a spotless record prior to his windfall, in 18 months Jack was ticketed over 250 times.

Before Brandi's death, her 17-year-old boyfriend had died three months prior, also from an overdose, in Whittaker's mountainside vacation home. Some of the kid's friends then robbed the house, stepping over the boy's lifeless body numerous times as they carried out valuables.

Somehow, this was Jack's fault.

The kid's parents sued him, claiming that his loose purse strings contributed to their son's death. Whittaker gave them a settlement, although he didn't really have a choice.  He'd already been found guilty in the court of public opinion.

Thereafter, more lawsuits followed. Jack was accused of ruining several marriages. Why?  His money made other men feel inferior. That was an actual complaint in one of the suits.  Whittaker settled these matters out of court four times. You read right. Four times.

Finally, his wife of 41 years divorced him and, in the process, froze most of his assets. As a result, Caesar's Palace in Atlantic City sued him for $1.5 million in lieu of bounced checks.

His 42-year-old daughter Ginger, the mother of Brandi, was also later found dead. No cause of death was ever determined.

In 2005, Jack was arrested for DUI. In his court appearance, his was a visibly broken man. Trembling and unable to keep his cool any longer, Whittaker took the opportunity to lash out at anyone that would hear him. Still reeling from his personal tragedies, he shouted about law enforcement ignoring the deaths of his family members and instead constantly harassing him.

It didn't matter. Jack was found guilty.

Jack's now ex-wife put it well. Had she known what would befall her family after the jackpot, she says, "I would have torn up that ticket."

Statistically, large jackpot winners face double-digit multiples of probability versus the general population to be a victim of:

1.  Homicide  (20 times more likely)
2.  Drug overdose
3.  Bankruptcy
4.  Kidnapping

And triple digit multiples of probability versus the general population to be:

1.  Convicted of DUI
2.  The victim of homicide at the hands of a family member
3.  A defendant in a civil lawsuit
4.  A defendant in felony criminal proceedings

So, yeah.

Someone is going to win over a billion dollars in the Powerball. Much more than Jack.

Just be glad that it ain't you.

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