Illinois Lottery jackpot (game not named in sources) · United States · 1996

Jeffrey Dampier Jr.

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.

What happened

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.

Where they are now

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.

The numbers behind this win

Keep reading

Sources

Every figure and quotation above comes from these.

Last verified: 2026-09-13