He Won $314 Million on Christmas Day. It Destroyed His Life.
“Jack Whittaker of West Virginia won the largest undivided Powerball jackpot in history on Christmas 2002. Within five years, his granddaughter was dead, his wife left him, and his fortune was gone.”
Andrew 'Jack' Whittaker was already a wealthy man on Christmas Eve 2002. As president of Diversified Enterprises Construction, a contracting firm based in Putnam County, West Virginia, his company employed over 100 workers and generated millions in annual revenue. His net worth was estimated at $17 million. He was happily married to his childhood sweetheart, Jewel, for 42 years. His 15-year-old granddaughter Brandi Bragg was the center of his world — friends said they spent their evenings eating popcorn and watching TV together in bed.
That morning, Whittaker stopped at the C&L Super Serve grocery store in Hurricane, West Virginia — a place where the regulars called him 'the Cowboy Man' because he always wore a black cowboy hat. He ordered his usual: two biscuits and bacon sandwiches. He wasn't a regular lottery player, but he knew the Powerball jackpot had climbed past $300 million, so he bought $100 in tickets. He fell asleep before the drawing that night. When he woke up on Christmas morning and checked his numbers, he felt sick to his stomach. The jackpot was $314.9 million — the largest single-ticket prize in American history at the time. He chose the lump sum: $113,386,407.77 after taxes.
Whittaker started by doing nearly everything right. He pledged 10% to Christian charities and donated $14 million to establish the Jack Whittaker Foundation, a nonprofit providing food, clothing, and assistance to low-income families in rural West Virginia. He funded the construction of a multimillion-dollar Church of God sanctuary in Hurricane. He bought the deli attendant who sold him the winning ticket a house, a car, and wrote her a check for $44,000. He set up trust funds for Brandi's education and gave her a weekly allowance of $2,100. He told reporters: 'I just want to thank God for letting me pick the right numbers.'
The unraveling began less than eight months later. On August 5, 2003, thieves broke into his car while it was parked at a strip club in Cross Lanes, West Virginia, and stole $545,000 in cash he kept in a suitcase. When reporters asked why he carried that much money around, his answer became infamous: 'Because I can.' Two club employees — the general manager and a dancer — were later arrested for plotting to drug his drinks and rob him. On January 25, 2004, another $200,000 was stolen from his car at the same club, though this time the money was recovered.
Then came the tragedies that would define his story. On September 16, 2004, Jesse Tribble, 18, Brandi's on-and-off boyfriend, was found dead in Whittaker's home in Teays Valley from a drug overdose. Just three months later, Brandi herself was reported missing on December 9. On December 20, 2004, her body was found wrapped in a plastic tarpaulin behind a junked van on a friend's property in Putnam County. She was 17 years old. Cocaine and methadone were found in her system. The cause of death was listed as 'undetermined.' No one was ever charged. Brandi was buried on Christmas Eve 2004 — exactly two years to the day after Whittaker bought his winning ticket.
The destruction continued relentlessly. Jewel filed for divorce in 2008, ending their 42-year marriage. The legal proceedings dragged on until 2011, when the West Virginia Supreme Court had to intervene. Whittaker was sued by Caesars Atlantic City for bouncing $1.5 million in checks to cover gambling losses. In July 2009, his daughter Ginger — Brandi's mother — was found dead at her home in Daniels, West Virginia, at age 42. In December 2016, his home in Bland County, Virginia, burned to the ground. His wife, who was inside at the time, barely escaped. The house was not insured.
In what may be the most-quoted statement by any lottery winner, Whittaker told ABC News near the end: 'I pretty much lost everything I held dear in my life. I don't like the hard heart I've got. I just don't like what I've become.' He said he wished he had 'torn that ticket up.' Jack Whittaker died on June 27, 2020, at age 72 — quietly, without scandal, without fortune, and without the family that had once made his life complete. His story remains the most frequently cited cautionary tale in American lottery history. Statistics suggest roughly 70% of major lottery winners lose their money within a few years.