Somehow it’s hard to feel bad for this guy.

CNN.com has an article up on Jack Whittaker who won a $315 million Powerball lottery some five years ago and is now wondering if it was worth it:

The jackpot that was the stuff of dreams turned into a nightmare: His wife left him and his drug-addicted granddaughter—his protege and heir—died. He endured constant requests for money.

Almost five years later, Whittaker is left with things money can’t cure: His daughter’s cancer, a long list of indiscretions documented in newspapers and court records, and an inability to trust others.

“I don’t have any friends,” he said in lengthy interview with The Associated Press. “Every friend that I’ve had, practically, has wanted to borrow money or something and of course, once they borrow money from you, you can’t be friends anymore.”

It sounds like he’s had a rough time, but the more you read the more you have to wonder how many of his problems are so much the result of winning the lottery or just bad decisions on his part. To begin with I’m not sure why you can’t still be friends after loaning one of them some money. I still technically owe my friend Bob for the Amiga 3000 I bought off of him over a decade ago, but I digress.

This isn’t a rag to riches story by any stretch of the imagination, though, as Whittaker was already a successful businessman with a pipeline business worth $17 million at the time he won. His family wasn’t exactly hurting for cash and he admits they lived what some folks would consider a lavish lifestyle. What changed with the lottery wasn’t so much the extra money, he opted to take a lump sum of $170 million which after taxes ended up more along the lines of $93 million, but the celebrity that came along with the prize. That’s when he says his problems really started:

Whittaker’s struggles with drinking, gambling and philandering became public, and tales of his transgressions were retold with relish.

His home and car were repeatedly burglarized. At a strip club, thieves broke into his Lincoln Navigator and stole a briefcase stuffed with $245,000 in $100 bills and three $100,000 cashiers checks. The briefcase was later found, with the money.

Whittaker was charged twice with driving while under the influence and sued repeatedly, once by three female casino employees who accused him of assault.

In all, Whittaker says, he’s been involved in 460 legal actions since winning. He recently settled a lawsuit that alleged his bank failed to catch $50,000 in counterfeit checks cashed from his accounts.

Whittaker believes he has been unfairly demonized by the media, which he says exaggerated his problems and helped drive his wife away.

As I said, sounds more like a lot of bad decisions more than anything else. Who leaves a briefcase with $245,000 in their car when they’re at a strip club? Fuck, who leaves $245,000 in their car anywhere? Granted, having his home broken into probably wasn’t his fault, but driving under the influence? Given his philandering it’s not hard to imagine him possibly assaulting casino workers. Initially I’m inclined to assume the identity theft wasn’t his fault until I remember he was dumb enough to leave over a quarter million in cash and checks in his car at a strip club and then I’m not so sure it wasn’t his own bad decision making that led to the ID theft.

The man has tried to do some good as well. He has a foundation he’s set up that doles out money to needy people and he is probably badgered quite a bit as a result of his notoriety celebrity. His company is said to provide with 200 people or so with well paying jobs. Like most folks he has his good side and his bad side.

But it still seems like he’s whining a bit too much in this article. That may be the fault of the reporter, but it’s hard to feel bad for a guy who has enough money that it’s the last thing he has to worry about when he has to confront the problems life presents him with. He can afford the lawyers and the medical treatment for the problems that come along. It’s also possible that it only seems that way to me because I don’t have the same kind of problems or the money that brings them about and perhaps it’s naive of me to think I have the maturity to handle the problems that would come from winning a lot of money, but I can’t help but think I could.

I won’t ask Mr. Whittaker for any of his money as it’s clear he’s tired of being asked, but I wouldn’t mind if one of the tickets I purchase in the near future gave me a chance to put my confidence to the test. At least I’d have the money to deal with whatever problems come along.

Sent along by Bog Brother.