Andrew Jackson "Jack" Whittaker Jr. of Putnam County won what was then the largest single lottery jackpot in history. The contractor, already wealthy from his businesses, won $314.9 million in the Powerball lottery on Christmas Day 2002. Whittaker, who was born October 9, 1947 at Jumping Branch in Summers County, chose to take the cash option and netted $113,386,407.77.

Whittaker gave substantially to charity from his lottery winnings, benefiting Church of God congregations in Putnam and Summers counties, among other groups. He established the Jack Whittaker Foundation to manage his charitable giving.

Following his winning of the Powerball jackpot, Whitaker received much unwanted attention, and personal troubles culminated in the death of his granddaughter. In 2003, he was temporarily robbed of $545,000 outside a Charleston-area dance club. The theft was the first of several involving Whittaker's vehicles, office, and house in Scott Depot. Problems afflicted Whittaker, including legal charges and arrests. He was the target of lawsuits. His granddaughter died in 2004. Her mother, Whittaker’s daughter, died in 2009. Whittaker was divorced in 2011. He moved to Virginia, where his house burned in 2016. He died June 27, 2020. He was 73.

On several occasions, Whittaker said he wished he had “tore up” the Powerball ticket. He told ABC News in 2007 "I pretty much lost everything I held dear in my life."