Not just any jackpot winner, but Jack Whittaker -- the largest single jackpot in U.S. history. He was the only ticket holder for the Christmas 2002 Powerball, winning $314.9 million. After taxes, and taken as a lump sum, he was handed a check for $113 million. He promised to donate 10% of his winnings to charity. (Oddly, he did not specify at the time how he would frivilously waste the other 90%.)

I don't know the guy, and I haven't read his life story. But recent media reports do not paint a rosy picture.

Last year, poor Jack almost lost $500,000 when his car got broken into in the parking lot of a strip club. The $500K cash was contained in a briefcase in the front seat, while his car was left running for more than 2 hours. Thieves must have got cold feet, though, as the briefcase and the money were found in a dumpster down the street a short time later. But the incident raised questions about (a) what a multi-millionaire was doing inside a strip club, (b) why he had $500,000 in cash on him, (c) why he left it in his car, and (d) why he left his car running for 2.5 hours.

The manager of the strip club and his girlfriend were charged in that case, for both the robbery and druggng poor Mr. Whittaker while the theft was going on. I suppose Jack isn't going back to THAT club any more.

So, maybe the media attention taught him to turn his life around? Rich guys don't need strippers. Rich guys date supermodels. Or, since Jack is married, maybe rich guys like him have supermodel mistresses. He's been quoted as saying, “I'm trying to be the good guy.“

Poor Jack has seen his car, business and home broken into “repeatedly”. In January 2003, his car was broken into an $100,000 was taken. In March 2004, within three days, both his vehicle and business were broken into and lost $2,000.

In the latest break-in, three men broke into his house and stole $15,000 worth of Jack's stuff. They “found” a dead body in the house, and called police after the fact. It turns out the robbery suspects are friends of the deceased, and the deceased was friends of Mr. Whittaker. At least one of the suspects had permission to be in the home, as there was no break in. Police believe the man died of a drug overdose.

Lots of questions are again being raised (by me, primarily): (a) why would Mr. Whittaker's friends rob him, (b) did Mr. Whittaker know his friend did drugs in his home, and (c) where was Mr. Whittaker at the time all this was going on.

Add in the facts that, in the last couple of years, he has been sued for assault by a racetrack employee (where he was gambling with a “female friend“), charged with drunk driving, and charged with threatening to kill the manager of a bar.

It must be strange to be in possession of so much money. Who can you trust? Is someone being friendly because they like you or because they are trying to get at your money? Money changes people, no doubt. Maybe Mr. Whittaker hasn't changed at all - but his friends and associates have. Everyone is trying to rob him. He doesn't seem to mind it though, as he continues to leave large amounts of cash in his car. Maybe winning the lottery is a curse.