Illinois Lottery jackpot (game not named in sources) · United States · 1996
Dampier was working as a security guard on Chicago's West Side when he and his then-wife won the Illinois Lottery jackpot in 1996 on a ticket held jointly. Sources do not record the draw date, the specific game or how the numbers were chosen.
Advertised prize
$20,000,000
Ticket
Not documented
Outcome
Ended in tragedy
The win was followed by a death or a violent crime.
Jeffrey Dampier Jr., born 24 March 1966 and raised on Chicago's West Side, was working as a security guard when he and his then-wife won an Illinois Lottery jackpot in 1996. ABC News put the prize at an estimated $20 million. The couple later divorced and split the money 50/50. Dampier then married Crystal Jackson, and about two years later the pair moved to the Tampa Bay area of Florida, where he invested in Kassie's Gourmet Popcorn in Tampa's Channelside entertainment district. He supported members of his wife's family, bringing her sisters Victoria and Terri Jackson to Tampa, and was having an affair with Victoria. On 26 July 2005 Victoria Jackson called Dampier to her apartment saying she had car trouble. Her boyfriend Nathaniel Jackson bound Dampier's hands and feet and forced him into a van at gunpoint, and Dampier was shot once in the back of the head. ABC News reported the pair were arrested three days after his body was found in Nathaniel Jackson's van. In September 2006 a Hillsborough County jury convicted Victoria Jackson of first-degree murder, armed kidnapping and armed carjacking, and she was given three life terms. Nathaniel Jackson faced the same charges and was also convicted.
Deceased since 26 July 2005. Victoria Jackson was convicted and sentenced to three life terms in September 2006 and Nathaniel Jackson was convicted of the same charges; a USA Today Network retrospective published in September 2025 still recorded both as sentenced to life in prison. No change is documented as of 2026.
One detail worth keeping
He put part of the winnings into Kassie's Gourmet Popcorn, a shop in Tampa's Channelside entertainment district, and was running it when he was killed.
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