Cops See Foul Play in Lotto Winner's Disappearance

Sheriff says Abraham Shakespeare's $11M windfall may have led to downfall.

January 25, 2010, 11:11 AM

Jan. 25, 2009 — -- The lure of the lottery is simple: A couple dollars buy a shot, however long, at millions upon millions. The unspoken promise, of getting rich quick, is older than the republic.

A penniless day laborer in Central Florida named Abraham Shakespeare was seduced by the promise in November 2006. When the delivery truck on which he was working stopped at a mini-mart in the tiny town of Frostproof, Shakespeare bought a couple Quick Pick Lotto tickets.

Shakespeare's numbers -- 6, 12 , 13, 34, 42 and 52 -- won the $30 million jackpot. He settled for a lump-sum payment of $16.9 million. After taxes, he was left with $11 million. Not bad for the son of a citrus picker who had made his living working garbage trucks and washing dishes, and who had served time in jail for a series of petty crimes.

But now, three years later, most of the money is gone, and so is Abraham Shakespeare.

"We have no idea where Abraham Shakespeare is," Polk County Sheriff Grady Judd said. "And we need to know that very badly."

Shakespeare, who would be 43 years of age, has not been seen since April 2009, Judd said. The Sheriff's Department wasn't told about his disappearance until November.

"In the beginning, we thought he was missing, that he was hiding away," Judd said.

"As the investigation continues, the evidence mounts that he could have died because of sinister means."

Somebody might have wanted that money, Judd said. And murder might have been their means to get it.

Indeed, a lot of people wanted Shakespeare's money. A man who had spent 40 years living on the margins was suddenly besieged with requests.

Shakespeare's mother, Elizabeth Walker, now a cafeteria worker, remembers what it was like in the months after her son became a millionaire.

"If someone asked him for help, he was always trying to help them," Walker said. "I had been with him in his car. They called him on his phone, and he trying to drive and trying to talk to them and they asking him for money.

"He said his phone would be constantly ringing. Even when I called him, he'll say -- he'll talk a few minutes and then he'll say, 'Hold on, I got a call. I'll call you back.' And sometimes, he wouldn't call back. And he said he was just getting phone calls, one right after another one. People just asking for money."

'Abraham Was Good-Hearted'

Shakespeare couldn't -- or wouldn't -- say no. He gave his stepfather $1 million, his three stepsisters $250,000 each. He paid off a friend's mortgage for $185,000. He paid off mortgages of $60,000 and $53,000 for two men he didn't know. He gave his brother's son's best friend $40,000.

"I would just like to say, I can't see how anybody being a human themselves that could take advantage of somebody else the way I see somebody done take advantage of my son, Abraham," Walker said. "Abraham was good-hearted. He paid for other people's funerals and he paid people's electric bills for them. He paid people's rent."

Then there was the court case. The man who was driving the delivery truck that stopped where Shakespeare bought the ticket insisted it was really his ticket. After a drawn-out trial, the jury sided with Shakespeare. But he was beginning to realize that money was not always a blessing.

"I really would like my old life back, where I could walk the streets like a normal person, without people coming and asking for money," Shakespeare said after the trial.

It's an all-too-common story for lottery winners. Months after Kenneth and Connie Parker, who lived in New York state at the time, won a $25-million jackpot, their marriage disintegrated. After Jeffrey Dampier won $20 million in the Illinois State Lottery, he was kidnapped and murdered by his own sister-in-law. And then there's West Virginian Jack Whittaker, who, in 2002, he won $314 million, the largest individual payout in Lotto history.

"I can take the money, I can take this much money and do a lot of good with this much money right now," Whittaker said at the time.

Not quite. Whittaker started out with good intentions, building churches, helping people in need, but the demands for money never stopped.

"It certainly had been a curse to me," Whittaker said. "Before I won the lottery, I thought you could probably control it. Since I won the lottery, I think, there is no control for greed. I think if you have something, there's always someone else that wants it."

Whittaker's marriage fell apart. His granddaughter died of a drug overdose. His daughter died from what is believed to have been a drug overdose.

"If I knew what was going to transpire, honestly, I would have torn the ticket up," said Jewell Whittaker, the lottery winner's ex-wife.

'Person of Interest'

Back in Lakeland, Fla., sheriff's investigators have been tracking Shakespeare's millions. They now believe that he burned through almost $10 million in three years.

Judd said less than $2 million of Shakespeare's money remains. He needed help in managing his newfound fortune, the sheriff said.

"The help -- the person that he thought was ultimately going to help him, the person that convinced him that she was there for his best interests, is Dee Dee," Judd said.

"Dee Dee" is Dee Dee Moore, 37. She befriended Shakespeare a year ago, when his millions were dwindling. She has not been charged with anything in connection with the case but Judd is not shy about saying she is the focus of the investigation of Shakespeare's disappearance and a "person of intense interest."

"Between January of 2009 and April of 2009, she was able to convince him to put all of his known assets, at least to us, in an LLC that she had the ability to cash checks on," Judd said. "The next thing we know, that money disappears from the joint LLC, after she redid the paperwork so he couldn't even cash checks on his own company.

"And she moved that money to her personal accounts and to her nursing staffing agency or medical staffing agency. ... That's what our investigation shows us at this point. And you know what she says? 'Abraham gave it to me as a gift for all the help that I gave him.' Almost $1 million."

Moore's credibility is not helped by a 2001 conviction for insurance fraud and falsely reporting a crime after she falsely accused three Hispanic men of raping her and stealing her car.

Moore now lives in and owns the $1 million home that Shakespeare bought in a gated community on the outskirts of Lakeland.

A call by "Nightline" from an intercom at the gate failed to connect.

But a neighbor who described her house and identified himself only as Justin said, "[There's] a lot of security around the house, lots of cameras."

'They Keep on and Keep on Asking'

In a home video posted on YouTube a year ago, Moore coaxes answers from a beleaguered Shakespeare.

"Do you get tired of people asking you for money all the time, Abe? Give me your opinion on that," Moore says in the video.

After some cross talk, Shakespeare replied: "They don't take no for an answer so ... and they keep on and keep on asking."

"So where you want to go to?" Moore asked.

"It don't matter to me," Shakespeare said. "I'm not a picky person."

"California? ... You want a foreign country? Cozumel? ... Hm? ... Well how about ... you going to miss your home?"

"Yup," Shakespeare said, "I miss it, but life goes on."

Moore's story is that Shakespeare wanted to disappear and she helped him. But now, she said, she can't find him either.

Sheriff Judd says he isn't buying it.

"We hope he has successfully hidden himself," said Judd. "But how many people do you know walking around just give you a million dollars? How many people do you know that create this illusion? ... She was texting from Abraham's cell phone to her cell phone and to other people's cell phone, giving the illusion that it was Abraham."

Moore told police she had Shakespeare's cell phone and sent the texts, Judd said, "because she was creating the illusion for him to stay hidden."

In the only interview she has given, Moore told the Lakeland Ledger she believes Shakespeare is still alive.

"I think that he'll pop up if he realizes how the extent, of what level this investigation is going to," she said.

She then cried as she complained about police searches of her home and car. "I'm done," she said. "What else can they do to me? They've turned my life inside out."

Moore's lawyer, Rusty Franklin, said his client has nothing to do with Shakespeare's disappearance. "Absolutely not true," he said, adding that it's inappropriate for the sheriff to comment publicly on an ongoing investigation.

Shakespeare's mother just wants to know what really happened to her son.

"I feel that something wrong," Walker said. "I really do. Because Abraham would have done called me. Even if he was leaving town, I believe he would have called me and said, 'Mom, I'm fixing to leave.'"

When he spoke with "Nightline," Sheriff Judd aired an appeal.

"If Abraham's alive," he said, "Abraham, just tell us where you are. We'll keep it a secret. We'll announce through our media outlets that, hey, we know where you are. You're alive, you're safe.

"You've proven that to us. And we'll leave you alone. You're an adult. You have a right to go where you want and be where you want."

There has been no response from Abraham Shakespeare.

Today, a Lakeland police officer was arrested for allegedly providing confidential police information to Moore in exchange for cash. Sheriff's investigators say Officer Troy McKay Young accepted cash from Moore in exchange for information he gave her from law enforcement data bases.

Young could not immediately be reached for comment.