Powerball · United States · 25 December 2002
He bought a Powerball quick pick on Christmas Eve 2002 at the a supermarket in Hurricane, West Virginia in Hurricane, West Virginia, a store he visited most mornings for a deli breakfast sandwich and fuel.
Advertised prize
$314,900,000
Cash value $170,500,000
Ticket
Quick pick
Outcome
Ended in tragedy
The win was followed by a death or a violent crime.
Andrew Jackson 'Jack' Whittaker Jr., a 55-year-old West Virginia construction contractor, bought a Powerball quick pick on Christmas Eve 2002 at the a supermarket in Hurricane in Hurricane, West Virginia, where he stopped most mornings for a deli breakfast and fuel. The Christmas Day drawing left his as the only winning ticket for an advertised $314.9 million, at the time the largest jackpot won by a single ticket in US history. He took the cash option, about $170.5 million before tax and $113,386,407 after withholding. Whittaker was already wealthy; the Associated Press reported his construction business was worth roughly $17 million. He pledged a tenth of the prize to Christian charities, funded a foundation in his name that built churches and distributed food, clothing and scholarships in rural West Virginia, and gave the store's deli manager a $123,000 house, a Jeep and a $44,000 cheque. Losses followed. In August 2003 thieves took a briefcase holding $545,000 — $245,000 in cash and three $100,000 cashier's cheques — from a suitcase at a strip club in Cross Lanes, West Virginia, although the briefcase and its contents were later recovered intact from his vehicle outside a strip club; his home and cars were burgled repeatedly. His 17-year-old granddaughter Brandi Bragg was found dead in December 2004 with cocaine and methadone in her system, cause undetermined. His daughter Ginger died in 2009, aged 42. In December 2016 fire destroyed his uninsured Virginia home.
Whittaker died on 27 June 2020, aged 72, of natural causes; the Ronald Meadows Funeral Parlor in Hinton, West Virginia confirmed his death on 30 June 2020 and the family held a private funeral. He had told the Associated Press years earlier: "I'm only going to be remembered as the lunatic who won the lottery. I'm not proud of that."
One detail worth keeping
He was already a millionaire before he played: the Associated Press put his West Virginia construction business at about $17 million when he bought the ticket.
Cheng 'Charlie' Saephan
Ended in tragedyPowerball · United States · 2024
$1,326,000,000
Laiza Chao joked to the Saephans before the draw that they were already "billionaires"; her $100 stake in a 20-ticket batch made it true.
Theodorus Struyck
Stayed privatePowerball · United States · 2023
$1,765,000,000
He bought the second-largest winning ticket in Powerball history about 500 yards from his own front door, at a cabin he had paid $90,000 for in 2010.
Edwin Castro
Went wellPowerball · United States · 2022
$2,040,000,000
The draw ran a day late: Minnesota's sales-verification system held up all 48 lotteries, so the $2.04bn numbers were drawn at 8:57 a.m. ET on 8 November 2022.
Manuel Franco
Stayed privatePowerball · United States · 2019
$768,400,000
He told reporters he had under $1,000 in his bank account when he spent $10 on the quick picks that won $768.4 million.
Cheng 'Charlie' Saephan
Ended in tragedyPowerball · United States · 2024
$1,326,000,000
Laiza Chao joked to the Saephans before the draw that they were already "billionaires"; her $100 stake in a 20-ticket batch made it true.
Theodorus Struyck
Stayed privatePowerball · United States · 2023
$1,765,000,000
He bought the second-largest winning ticket in Powerball history about 500 yards from his own front door, at a cabin he had paid $90,000 for in 2010.
Saltines Holdings, LLC (Miami, Florida)
Stayed privateMega Millions · United States · 2023
$1,602,000,000
The biggest Mega Millions winner in history is a company: Saltines Holdings, LLC of Miami. The Publix that sold the $2 Quick Pick collected a $100,000 retailer bonus.
Edwin Castro
Went wellPowerball · United States · 2022
$2,040,000,000
The draw ran a day late: Minnesota's sales-verification system held up all 48 lotteries, so the $2.04bn numbers were drawn at 8:57 a.m. ET on 8 November 2022.
Every figure and quotation above comes from these.
Last verified: 2026-09-13