[2] Before his lottery win, Whittaker had been the president of Diversified Enterprises Construction, a contracting firm in Putnam County, West Virginia, for 12 years.
[4] On Christmas Eve 2002, Whittaker purchased the winning Quick Pick ticket at a supermarket in Hurricane, West Virginia, where he had stopped for a deli breakfast sandwich and to get fuel for his vehicle.
He also donated $14 million to establish the Jack Whittaker Foundation, a non-profit organization that provides food and clothing to low-income families in rural West Virginia.
[6][8] On August 5, 2003, less than a year after Whittaker won the lottery, thieves broke into his car while it was parked at a strip club in Cross Lanes, West Virginia.
In another incident, two employees at the club, the general manager and a dancer-manager who were romantically linked, were arrested and charged with a plot to put drugs in Whittaker's drinks and then rob him.
[8] On October 11, 2005, at a hearing related to his January 2003 DUI, a visibly shaken Whittaker lashed out at local law enforcement agencies for focusing on his troubles while failing to arrest anyone in relation to his granddaughter's death, saying, "Go after whoever killed my granddaughter with as much zealous [sic] as these butt holes are trying to convict me of something I didn't do.
"[13] Whittaker was later sued by Caesars Atlantic City casino for bouncing $1.5 million worth of checks to cover gambling losses.
He countersued, claiming that his losses were supposed to be credited due to a slot machine he developed and that they, in fact, owed him money.