Abraham Shakespeare was a barely literate laborer who rode as a truck driver’s assistant in central Florida, owing back child support and living hand to mouth, when he bought a Florida Lotto ticket on a work trip in November 2006. It won a $30 million jackpot, and he took the discounted cash option of roughly $17 million. Almost immediately the money made him a destination: relatives, acquaintances, and total strangers came asking, and Shakespeare — a soft-touch who reportedly found it nearly impossible to say no — gave much of it away.
Into that swirl of need stepped Dorice “Dee Dee” Moore, who approached Shakespeare in October 2008 saying she wanted to write a book about how the lottery had brought him misery and hangers-on. Instead, prosecutors said, she methodically stripped him of what remained. She set up a company, Abraham Shakespeare LLC, took control of his accounts and real estate, and moved his assets and money to herself — prosecutors said she withdrew about $1 million and bought luxury vehicles, and had his home transferred to a company she controlled.
Shakespeare was last seen alive in April 2009. For months Moore told family and investigators he was alive and simply hiding from the people who wanted his money, even sending text messages from his phone and paying others to suggest he was in contact. On January 27, 2010, his body was found buried under several feet of dirt and a newly poured concrete slab behind a home connected to Moore in Plant City, Florida; he had been shot twice in the chest.
Moore was arrested on February 2, 2010, and charged with first-degree murder; on December 10, 2012, a Hillsborough County jury convicted her. She was sentenced to life in prison without the possibility of parole, plus a 25-year minimum for using a firearm in a violent felony. Shakespeare’s case is the starkest entry in this catalogue: not a slow squander or a self-inflicted ruin, but a man killed for a fortune that a predator decided was easier taken than earned.
Urooj Khan was a 46-year-old Chicago dry-cleaning businessman, an immigrant from India who ran Style Dry Cleaners on Devon Avenue on the city’s North Side. In the summer of 2012 he bought two $30 instant scratch-off tickets at a neighborhood 7-Eleven and one of them won $1 million on the Illinois Lottery — a stroke of luck made stranger by reports that he had recently sworn off gambling. He chose the single lump-sum payment, which after federal and state withholding came to roughly $424,000. The Illinois Lottery issued the check on July 19, 2012. The next day, Khan was dead.
He became violently ill at home overnight after a family dinner and was pronounced dead on July 20, 2012. The Cook County Medical Examiner’s office, finding no signs of trauma or foul play, initially certified the death as natural — attributing it to arteriosclerotic cardiovascular disease on the basis of an external examination rather than a full autopsy. That ruling stood only briefly. Khan’s brother, Imtiaz Khan, refused to accept that an apparently healthy man had died overnight and petitioned the medical examiner to look again.
When investigators retested preserved fluid samples, the final toxicology results in late November 2012 showed a lethal level of cyanide in Khan’s blood. The manner of death was reclassified as homicide, and in January 2013 his body was exhumed for a full autopsy to determine how the poison had been administered. By then the remains were too decomposed to retain cyanide, and the autopsy yielded no further clues — but the medical examiner, Dr. Stephen Cina, stood by the homicide ruling based on the original blood samples.
More than a decade later, the case remains open and unsolved. No one has ever been charged in connection with Urooj Khan’s death, and family members who were investigated have denied any involvement. Cursed Jackpot reports only what the medical examiner and investigators established — a death by cyanide poisoning, reclassified as a homicide — and makes no accusation against any living person. What is certain is the chilling sequence at the center of the file: a $1 million ticket, a check issued, and a man dead before he could spend a dollar of it.