Unlucky numbers: Florida man swindled, killed over lottery money

Abraham Shakespeare, 43, worked odd jobs at Greg Smith's barber shop in Lakeland, Florida, about 40 miles east of Tampa.

"He was the cleanup guy in my barber shop, he would do little miscellaneous things, clean up the outside, clean up the inside, mop the floors, clean the restrooms," said Smith.

Until one day in 2006 Abraham stopped coming to work.

"A couple of weeks passed and I didn't see him, I'm like 'Where is Abraham at?' So I called him and was like, 'Are you coming in to clean the bathrooms, you ain't cleaned outside yet.' He said 'I hit the lottery,'" said Smith.

Smith thinks Abraham is merely being theatrical. But it's true: He is the lucky winner of a whopping $30 million.

"I was standing in front of the barber shop cutting hair and I could see right out my door," said Smith. "I seen this black BMW pull up. I'm like, 'Who in the devil is that?' I'm looking out the window and he gets out of the car. I said, 'Man, you need to take car back man, whoever's car you're washing you need to take it back.' He was like, 'Man, I hit the lottery.'"

Abraham takes one lump sum of $17 million instead of yearly payments on the winnings. He buys a $1.1-million home in a gated community near Lakeland, and buys some new cars.

"He did it out of the goodness of his heart," said Smith. "A whole lot of them took advantage of it, but you know what, he gave to them, they didn't take it. He gave it to them."

Abraham even insists on helping out his old boss, Greg Smith, loaning him $63,000 after his mother's house goes into default.

"I didn't want to borrow no money from Abraham," said Smith. "I had gone to the bank and gotten a loan. He actually left first and went and got a cashier's check with my name on it. I said 'But before I do that I need to get with my accountant and we draw some papers up so we do it official. 'Cause I'm gonna do you the same way I was gonna do the bank.'"

But Abraham Shakespeare is ill-equipped to handle his newfound wealth. He cannot read or write, and knows nothing about investing.

Eleven months after winning the lottery, Abraham meets a woman named Dee Dee Moore. She runs a successful nurse-staffing agency near Lakeland and also tells Abraham she wants to write a book about him, and help him manage his money.

The book is never written. But within six months of meeting him, Moore has managed to transfer ownership of Abraham's home and control of his bank accounts to her company before giving herself a nice vacation.

Of the total $570,000 loaned out by Abraham to various people, more than two-thirds of it is owed by Dee Dee Moore's company. She also starts going after the money owed him by all his debtors.

About that time Abraham's friends realize they haven't seen him in a while. Moore tells them that he's laying low and wants to get away from the constant pressure of people looking for money.

"'He's on vacation, he's in Miami.' 'He's in Texas,' 'He's on a cruise, he's over helping the people in Haiti. He can't get back across because of the earthquake,'" said Smith, describing Moore's explanations.

A cousin of Abraham's becomes suspicious. He files a missing-persons report with the sheriff's office. Moore is now on police radar. And they want to talk to her.

Hillsborough County Sheriff's Detective Greg Thomas knows the case well.

"Polk County Sheriff's Office began a pretty long-term investigation. Over a couple of months they basically were able to determine through cellphone work and just surveillance that obviously Dee Dee Moore had something to do with the disappearance of Abraham Shakespeare," said Thomas. "It was not known if he was just missing or if he was dead."

Moore turns to Abraham's good old friend Greg Smith for help.

"She's crying, I'm like 'What's wrong with you?' She's like 'Everybody thinks I did something to Abraham,' and this and that," said Smith. "And I said 'Well listen, did you?' 'No, Abraham is on his way back.'"

And then she makes such an incredible request that, to this day, Smith wonders how he could have gone along with it. But he does.

"She says 'Listen: I need you to do me a favor to buy me some time till Abraham come back. Can you tell Abraham's mother that 'I'm OK'? I say 'I'm OK?' 'I want you to pretend to be Abraham.' I said, 'Man, I don't know,'" said Smith. "She said, 'I tell you what. I'll give you $300 to make the phone call.' I say 'OK. Three hundred dollars I'll make a phone call and say you OK.'"

"She chose to take Abraham Shakespeare's mother to a restaurant where it would be loud," said Thomas. "As they were sitting there at the table, the phone rings and Dee Dee tells Abraham's mother 'That could be your son, why don't you go ahead and answer it, it could be Abraham calling.'"

"She said 'Hello,' and I pretended to be Abraham, I was like 'Hello, what's up mama?' And she was like 'Who is this?' and I said 'This is Abraham. I just got a little cold and I'm kind of frustrated.' She say 'OK baby,' she said 'When you coming home?' I said 'I'll be home real soon and you can tell the police that I'm OK.'"

Up to this point, Smith has given Moore the benefit of the doubt on her Abraham Shakespeare story.

"I'm not thinking something's wrong with him," said Smith. "At worst, worse he done and went and hid from Dee Dee, that's what I'm thinking that 'Abraham is tired of you, he went and hid from you.'"

But he's getting more suspicious by the day.

"I called Abraham, 'Hey man, call me,'" said Smith. "He never called me back, and then I got this text, 'I'll call you in a little while,' so I'm looking at the text and I'm like, something ain't right. He don't even know how to spell."

And now it looks like Greg Smith is on the cops' radar too. They catch up with him after they observe Dee Dee Moore handing him $300 for making that phone call to Abraham's mother.

But the cops have an incredible request of their own.

"At that point the investigators told Greg Smith that Abraham had been reported as a missing individual and he had the option of assisting them in their investigation," said Det. Thomas.

"They say 'We got suspicions that this woman had did something to Abraham. We need some help,'" said Smith.

In a matter of months Greg Smith goes from cutting hair to possibly cutting a deal with police that could turn his world upside down.

"If you had gotten to know me, let's clear the slate. I ain't the snitch on the streets," said Smith.

Smith must decide whether to be an undercover informant in the investigation of Abraham Shakespeare's disappearance. The decision is an easy one.

"Listen, this dude bailed me out of a $63,000 debt. He's my friend. He helped me when nobody else would," said Smith.

Police fit Smith with a body wire for his next meeting with Dee Dee Moore, who befriended Abraham and took control of his newfound fortune. But that's not the barber's style. He's already uncomfortable with the arrangement.

"Dee Dee Moore was trying to was I wired up one day and she grabbed me and I told her, 'Get your hands off of me, as a matter of fact get out of my car. You don't trust me, I don't trust you, get out of my car,'" said Smith. "I scared to death because I think she touched it. They was trying to make me a leader, trying to make me force her to do this and that, and I told them 'No. I'm from the streets. I know how to do this.'"

Smith came up with a better idea.

"I took the Red Bull can and I shaved the top of it off so that the inside cap would pop open," said Smith. "I took a small recorder and set it inside of it and put Styrofoam so it wouldn't move and so it felt like there was something inside of the can."

He places the can in the center console cup holder.

"I was smoking cigarettes so I would use the top of it like I was dumping ashes in it in a Red Bull can like it was my ashtray," said Smith. "The whole time it was my recording device."

"It worked," said Det. Thomas. "It was just a simple tool that he utilized and put together and it clearly recorded what we needed."

Police turn up the heat on Moore.

"She was feeling pressure from the investigators. They were knocking on her door all the time wanting updates, 'When's the last time you heard from Abraham' and so forth," said Det. Thomas. "And so she had to continue this evolving lie."

She started telling Smith about a character named "Ronald."

"Ronald was crazy," said Smith. "Ronald was the guy that she was trying to say that was threatening her and actually was a drug dealer that possibly killed Abraham."

"And that's the part of the investigation where she's seeking somebody that's looking at a significant prison sentence to take the rap for Abraham Shakespeare's disappearance and murder," said Thomas.

Taking their cue from Moore's script for a Shakespeare cover story, cops bring a new actor onto the stage.

"That then puts in motion utilizing a covert officer to play the part of an individual about to be sentenced to a lengthy prison term," said Thomas. "She's asking him to remove the body of Abraham Shakespeare, dispose of it, and then once he begins his prison sentence to basically admit to the homicide."

The undercover "fall guy" agrees to the deal for $50,000 to be paid to his family after he goes to jail. Moore knows a deal when she sees one. But there's one more thing cops want in the bargain.

"Basically advises Dee Dee Moore that he will need some form of evidence to convince the investigators that he is the perpetrator of the crime," said Thomas.

"It made me feel like OK, mission's not over, it's not complete," said Smith. "It was heartbreaking but at the same time it was a blessing to be able to help him out like he helped me. Never in a million years would I have though that a $63,000 loan would be the payoff for me to find that my partner was a murdered man."

All Smith needs to get is the murder weapon from Moore. And police add one more thing to their wish list: They also want Smith to get her to tell him where the body is buried.

"I tell her, 'Listen, if we going to convict this guy, let me get the gun. If you got it. I ain't saying you got it, but if got it, if you know who got it, bring me the gun that killed him so we can pin it on him.' She brings me the gun," said Smith.

"It was a Smith and Wesson hammerless .38 Special with an integrated laser sight, which we had found receipts of her purchasing at a local gun shop and actually training and using the firearm at the local gun shop range," said Det. Thomas.

"Then she tells me about where Abraham is buried at," said Smith.

Moore takes Smith to a property she owns in nearby Plant City, Florida and points out a big fresh slab of concrete in the yard.

"When she took me to the body, we had a piece of rebar iron that was over by the concrete," said Smith. "I told her 'Listen, I don't want to get out of the truck 'cause I don't want anybody to see us together. What I want you to do is to take that piece of steel and go set it on the concrete where his body is buried.'"

That same day police move in to take over.

"We had secured the entire property with deputies and we were going hold it until the following morning when we can get heavy equipment and the right personnel out there to begin basically an exhumation," said Thomas.

Police say that only six months after meeting him, Moore and Abraham had an argument.

"It appears that they probably got into some type of disagreement over his money and access to his accounts," said Thomas. "It appears that she placed two rounds into his abdominal region and chest region."

Police say that Moore had her ex-husband dig a hole with a backhoe, telling him only that she needed a pit to burn trash. They say Moore dumped the body herself, then hired a contractor who unknowingly covered it with concrete.

"Her excuse that she made was that she wanted basically a solid concrete pad to park her boat and some vehicles on," said Thomas.

And Moore has plenty of other cover stories as well. Remember "Ronald," the character she made up, a drug dealer who was threatening her?

"She brought up the name of a black drug dealer named Ronald that was actually conducting a drug deal at her office location and was the one to shoot and kill Abraham Shakespeare," said Det. Thomas. "I confronted her and advised her that that person did not exist, but she was adamant and then changed her story to it was a white drug dealer named Ronald. Again we confronted her about this fictitious person and then she went on to another statement, blaming her son, who was 14 years old at the time, that actually shot and killed Abraham Shakespeare at her office."

Moore went before judge and jury, charged with murder in the first degree. She does not testify on her own behalf, but makes so much noise the judge cuts off her microphone at the defense table. She is found guilty and sentenced to life in prison without parole.

Crime Watch Daily paid her a visit at the Lowell Correctional Institute in Ocala, Florida to get her story -- but we were forewarned.

"It's very frustrating interviewing Dee Dee Moore. I think she loses herself in her stories and her lies and cannot remember one lie from the next," said Thomas.

What did Abraham see in Dee Dee Moore?

"My personality," said Moore. "I stay up when things get down, I try to look at the upside, so when things in life go bad I try to look at the bright side. Maybe I'm here to change something about the system.

"See I thought [Greg Smith] had something to do with Abraham's death to begin with," said Moore. "I was surprised that he was dealing with the cops. And why? You know, they have to have somebody charged with the body to get at my assets. They want my house, they want my cars, they want my money. They want what Abraham had, plus what I have. To get that they got to eventually uncover this body.

"If I killed this man, I would have not even dug. If I know he's in my yard, why would I go and keep searching? The cops can't do nothing to me, they can question me and I can refuse," said Moore. "I had no clue and I kept thinking I wanted to know what happened. They threatened they were going to kill my son, chop him up in little pieces and put him on my doorstep."

"It was money, it was money. We buried money," said Dee Dee Moore.

For the record, the only money found in that hole exists in Moore's mind.

But minutes after saying she has no idea who killed Abraham, she suddenly remembers.

Who do you believe murdered Abraham and buried him in your back yard?

"Ronald."

Meanwhile, Greg Smith went back to his barber shop. He lost his good friend Abraham Shakespeare, but he sure has some great stories to tell.

"He end up sweeping in the barbershop -- millionaire, straight millionaire, millions of dollars -- he still used to come to sweep the barber shop, right. Picking up pennies off the ground," said Smith. "I said what you picking pennies up for? He said, 'Boy, I got millions of dollars, but pennies make dollars.'"