In 2002, West Virginia building contractor Andrew Jackson Whittaker Jr. walked away with $114 million after taxes on a $315 million multistate Powerball draw.

That was just about his last stroke of good fortune.

Thieves ran off with $545,000 Whittaker stashed in his car. Later on, he was sued by Caesar's Atlantic City for allegedly bouncing $1.5 million in checks.

Within four years, his fortune was gone.