Wherefore art thou, Mr. Shakespeare?
A truck driver's assistant who won $16.9 million in the Florida lottery in 2006 is feared dead after not being seen by friends or relatives since April. Abraham Lee Shakespeare, 43, was reported missing by a police informant in November.
"There are a lot of odd and bizarre circumstances in this case," Polk County Sheriff Grady Judd said. "We fear and are preparing for the worst. We're working this case as if it were a homicide."
Donna Wood, public information officer for the Polk County Sheriff's Office, said authorities are particularly concerned about Shakespeare since he did not contact relatives during the holiday season.
"No one has been able to confirm his well-being," Wood told FoxNews.com. "We continue to be quite concerned."
Wood declined to discuss information pertaining to when Shakespeare last spent any of the millions he won three years ago. A $5,000 cash reward continues to be offered for information on his whereabouts.
Elizabeth Walker, Shakespeare's mother, said she hopes her son — a tall, slender man who wears his hair in dreadlocks — is somewhere in the Caribbean, soaking up the sun on white sandy beaches and away from the hangers-on who were consistently asking him for money.
"I feel like running away somewhere," Walker told FoxNews.com. "I don't know what happened to my son but I can hardly concentrate on anything else."
Walker, 68, said she expected to hear from Shakespeare during the holidays. Now, she wishes her son had never struck it rich.
"I'm so sick and confused over not knowing where Abraham is," Walker continued. "It was just yesterday I was thinking to myself that I would've rather him worked on the garbage truck that came by Monday."
Shakespeare won a $30 million jackpot but chose to receive a lump-sum payment of $16.9 million instead of a million dollars a year for 30 years. He bought a Nissan Altima, a Rolex watch and a $1 million home in a gated community — and he spoke about establishing a foundation for the poor.
"I'm not a material person," Shakespeare said in 2007. "I don't let material things run me. I'm on a tight budget."
But the financial windfall quickly caused problems for Shakespeare. He was sued in 2007 by a co-worker who claimed he had given money toward the winning ticket. A jury later ruled that the ticket was purchased solely by Shakespeare.
"I liked Abraham," attorney Jim Valenti, who represented Shakespeare in the lawsuit, told FoxNews.com. "I thought he had a lot of guts, he could've settled that suit for just a fraction of what the guy was asking for."
Instead, Valenti said, Shakespeare insisted he owed no one.
"He was absolutely right," Valenti said. "He stuck to what he believed in and won."
Valenti described Shakespeare as a friendly man despite his criminal record, which includes multiple arrests and prison time for burglary, battery and not paying child support. But he said Shakespeare frequently traveled with a large entourage.
"He was very generous from what I could tell, but he was surrounded by some folks who did not have his best interest at heart," he said. "When Abraham understood something, he made good choices in what direction to go. But I think a lot of people were whispering in his ear and I think he was taken advantage of."
Valenti said he last spoke to Shakespeare two years ago and is not surprised that he hasn't been seen lately.
"He seemed to be kind of a private person and didn't want people to know what was going on," he said. "He wasn't a talker, he wasn't loquacious."
He said Shakespeare appeared to be someone who could protect himself if necessary.
"If you met Abraham out at a Publix or whatever, you would think he was someone to take seriously," he said. "He was not threatening, but you'd want to take him seriously."
Shakespeare's mother could not be reached for comment on Wednesday, but she has said that people constantly asked her son for money after he won the jackpot.
"They didn't wait," she said. "They just came right after they found out he won this money."
Walker said her son paid for funerals, lent money to friends starting businesses and even gave a million dollars to a person known only as "Big Man."
Shortly after buying his home in early 2007, Shakespeare was approached by a woman named Dee Dee Moore, who said she was interested in writing a book about him and began serving as his financial adviser of sorts, according to relatives and officials.
Property records indicate that Moore's company, American Medical Professional, bought the home for $655,000 last January. Walker said she saw her son for the last time shortly afterward.
According to The Ledger of Lakeland, Fla., Moore, 37, contacted reporters at the paper in April and said Shakespeare was "laying low" because people had tried to pilfer money from him. Then, on Dec. 5, Moore told the newspaper she helped Shakespeare disappear, but now wanted him to return since detectives had been searching her home and car looking for evidence.
Judd told Fox News on Wednesday that Moore, who could not be reached for comment, is a "person of interest" in the case.
The Associated Press contributed to this report.