Shakespeare vanished months ago. His mother hopes he is somewhere in the Caribbean, lying on a beach and enjoying the good life away from all the hangers-on who were constantly hitting him up for money.
The sheriff has a more ominous theory: Shakespeare was killed.
"There are a lot of odd and bizarre circumstances in this case," Sheriff Grady Judd said. "We fear and are preparing for the worst. We're working this case as if it were a homicide."
Polk County Sheriff's Office / AP
Abraham Shakespeare, 43, won $30 million in the Florida lottery in 2006. He disappeared months ago, and authorities fear he may have been killed.
Shakespeare, 43, won the big jackpot after buying a lottery ticket at a convenience store in a town called Frostproof, claiming later that he gave the last $3 in his pocket to a homeless man just before the winning numbers were announced.
Shakespeare - who had a criminal record that included arrests and prison time for burglary, battery and not paying child support - took a lump-sum payment of $16.9 million instead of annual installments.
He bought a Nissan Altima, a Rolex from a pawn shop, a $1 million home in a gated community. He talked about starting a foundation for the poor and insisted the money wouldn't change him.
"I'm not a material person," he said in 2007. "I don't let material things run me. I'm on a tight budget."
The money quickly caused him problems.
A former co-worker sued him in 2007, accusing Shakespeare of stealing the winning ticket from him. Six months later, a jury ruled the ticket was Shakespeare's.
Then there were the people constantly asking him for a piece of his fortune.
"They didn't wait. They just came right after they found out he won this money," his mother, Elizabeth Walker, said recently.
She said her son was generous, paying for funerals, lending money to friends starting businesses and even giving a million dollars to a guy known only as "Big Man."
Not long after he bought the million-dollar home in early 2007, he was approached by a woman named Dee Dee Moore, said family and officials.
Moore - who could not be reached by The Associated Press - said she was interested in writing a book about Shakespeare's life. She became something of a financial adviser to Shakespeare, who never graduated high school.
Property records show that Moore's company, American Medical Professionals, bought Shakespeare's home for $655,000 last January. His mother said the last time she saw him was shortly afterward, around her birthday in February.
The sheriff said the last time anyone saw Shakespeare was in April - but it wasn't until Nov. 9 that he was reported missing, by a police informant.
And the story gets more bizarre.
According to The Ledger of Lakeland, the 37-year-old Moore contacted reporters at the newspaper in April, saying Shakespeare was "laying low" because people tried to suck money out of him.
That made sense to Shakespeare's mother - sort of. "I remember once, talking with me over the phone, he said he might go to Jamaica," she said.
On Dec. 5, a sobbing Moore told The Ledger that she helped Shakespeare disappear, but now wants him to return because detectives were searching her home and car and looking for blood on her belongings.
One reason he wanted to leave, she said, was a child support case for a child he allegedly fathered after winning the lottery. "Abraham sold me his mess to get a better life," she told the paper.
She even gave the paper a video that she said she took of Abraham. In the video, he says he is tired of people asking him for money. "They don't take no for an answer," he says.
"So where you wanna go to?" Moore asks in the video.
"It don't matter to me. I'm not a picky person," Shakespeare replies.
Moore told the paper that she took the video to "protect herself."
Moore said she filed paperwork to take over five mortgages totaling about $370,000 that had been owed to Shakespeare. She said she sold the loans at a loss to another person. She added that many of the people who borrowed from Shakespeare have refused to pay, and she feels threatened by some of them.
Moore's past includes a year of probation after she was charged with falsely reporting that she was carjacked and raped in 2001. Officials said she concocted the scheme so her insurance company would reimburse her for the SUV, which she claimed had been stolen.
The woman did not answer several calls placed to a number listed for her in public records. During a recent visit to the home she bought from Shakespeare, a security box rang to a phone number that had been disconnected.
Sheriff's officials won't comment on Moore's involvement in Shakespeare's life.
The sheriff said that Shakespeare spent the bulk of his lottery winnings. The fact that he didn't call his mother on Christmas reinforces the theory that Shakespeare is not just hiding, Judd said.
"I hope so much that he is alive somewhere," said his mother. "And I want people to know, if they ever win the lottery, I hope they know how to handle the people that come after them. They can be dangerous."
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