Florida Lotto · United States · 15 November 2006
Riding in a truck with driver Michael Ford on a delivery run, Shakespeare handed over $2 from a wallet holding $5 for two Florida Lotto tickets bought at a convenience store in Frostproof, Florida.
Advertised prize
$30,000,000
Cash value $17,000,000
Ticket
Not documented
Outcome
Ended in tragedy
The win was followed by a death or a violent crime.
Abraham Lee Shakespeare was a 43-year-old labourer and truck driver's helper with a criminal record and, by the accounts of those who knew him, barely able to read. On 15 November 2006, on a delivery run with driver Michael Ford, he put in $2 from a wallet holding $5 for two Florida Lotto tickets bought at a convenience store in Frostproof. One matched all six numbers for a $30 million jackpot. Shakespeare took the lump sum of about $17 million rather than annual payments of roughly $1.5 million. Ford sued, claiming Shakespeare had taken the ticket from his wallet; on 19 October 2007 a jury rejected the claim after little more than an hour. Shakespeare gave and lent money away steadily, including six-figure sums to relatives, a $1 million gift to his stepfather and mortgage payoffs for friends, and within two years most of it had gone. In 2008 Dorice "Dee Dee" Moore approached him through his realtor, saying she wanted to write a book about him, and took control of his finances through a company set up in his name. He was last seen in April 2009 and reported missing on 9 November 2009. On 26 January 2010 his body was found under a concrete slab behind a Plant City property linked to Moore, shot twice in the chest.
Moore was arrested in February 2010, convicted of first-degree murder in December 2012 and sentenced to life without parole plus a 25-year minimum for using a firearm in the felony. Interviewed by ABC News from prison in April 2025, she still maintained her innocence; three appeals had failed, the most recent in 2023 (2025).
One detail worth keeping
The trial judge, Emmett Battles, called Moore "cold, calculating and cruel" and the most manipulative person he had encountered on the bench.
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