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From the archives: Abraham Shakespeare won the lottery, then lost it all

Florida Lotto winner Abraham Shakespeare listens as a judge discusses jury selection during the start of a civil trial with his former co-worker Michael Ford of Zephyrhills. Ford accused Shakespeare of stealing a winning lottery ticket worth $31 million. Shakespeare prevailed, but would go on to squander the $17 million lump sum payment he took. Winning the lottery would also lead him to Dorice "DeeDee" Moore, who authorities said killed the 43-year-old Lakeland man and took whatever he had left. In 2012 a Hillsborough County jury found her guilty of his murder. She is now serving a life sentence at Lowell Correctional Institution, a women's prison in Marion County. [Ledger/Michael Wilson | Florida Department of Corrections]
Published Jan. 24, 2018

Editor's note: The most infamous lottery winner in Tampa Bay history may be Abraham Shakespeare. In 2006 the 41-year-old illiterate, part-time garbage worker from Lakeland won a $30 million jackpot on Nov. 15, 2006. He was killed two years later after squandering the $17 million lump-sum payment. His winnings also led him to Dorice "DeeDee" Moore, who authorities said would take whatever he had left and then kill him on April 6 or 7, 2009. Shakespeare was reported missing in November 2009, and the Times published this story about his life on Dec. 13, 2009. His body was found in January 2010, Moore was arrested for first-degree murder a month later and found guilty in 2012.

Before Abraham Shakespeare became the most famous missing man in Central Florida, before he won the lottery, before he went on a spree of either stunning generosity or profligate stupidity, before a co-worker sued him saying he had stolen the ticket, before a woman showed up late last year and ended up living in his palatial home after he had disappeared - before any of that - the lanky black man with the dreadlocks was the broke son of a citrus picker.

On Nov. 15, 2006, Shakespeare was 41 years old, had $5 in his wallet and was making eight bucks an hour.

He had no car, no driver's license, no credit card. He had grown up in Lake Wales and spent time in homes for juvenile delinquents. He could read and write, but not much.

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He had a long criminal record. Mostly he loitered, he drove when he wasn't allowed to drive, he stole, he hit people, and later he didn't pay for the children he fathered. He went to prison twice. After he got out in 1995 he lived with his mother.

He worked as a garbage man. He unloaded trucks. He washed dishes. He did day labor.

That's what he was doing that day in November 2006. He was assigned to ride shotgun for a truck driver named Michael Ford on an overnight food route to Miami. They made a delivery in Lakeland. They made a delivery in Winter Haven. Then they stopped at the Town Star mini-mart in Frostproof.

Ford asked Shakespeare if he wanted anything. Shakespeare asked for a pair of Quick Picks and gave Ford two of his $5 bills when he returned.

FROM 2012: Jurors quickly find DeeDee Moore guilty of lottery winner's murder

That's how he ended up with the ticket with the numbers 6, 12, 13, 34, 42 and 52. The jackpot was $31 million. He took it in a lump sum of $16.9 million. After taxes, he later said, he got $11 million and change.

Still, he thought, this was his dream. He was rich.

Within three years, most of his money would be gone — and Shakespeare, too.

• • •

The first thing that happened was the government took the child support he owed — almost $9,000. He later put $1 million in a trust fund for his son.

He gave his stepfather $1 million. He gave his three step-sisters $250,000 apiece. He paid off $185,000 of a mortgage for a friend, he paid off $60,000 of a mortgage for a man whose last name he didn't know and he paid off $53,000 of a mortgage for a man "out of the neighborhood" who he'd "been knowing for a few years."

He bought for $125,000 a house near Lake Wales that he had seen only once and rented it to some tenants he had met only once. He gave his brother's son's best friend $40,000. He gave his mother $12,000 and his sister $10,000. He wrote Wachovia cashier's checks to friends. He paid for funerals.

It was "common knowledge" around town, Polk County Sheriff Grady Judd said last week, that people were "tugging on him."

For himself, he bought a 2006 F-150 pickup, a 2007 BMW 750i, and a new home, too.

The elaborate brick and tan stucco house at 9340 Red Hawk Bend Drive is in the rural area north of town, past some orange trees and a horse farm called Heaven Sent Acres, a long 10 miles from his old neighborhood.

Its 6,519 square feet include an enclosed pool and two two-car garages and it sits behind a fence in a community behind a gate. Shakespeare bought it in January 2007 for not quite $1.1 million. It came with surveillance cameras.

• • •

Shakespeare was sued three months after he bought the house. The man who sued him was Michael Ford - the truck driver.

The winning ticket, claimed Ford, 34, was his, and the money, or at least what was left of the money, should be his, too.

"From my background investigation, he was always kind of a transient type," Ford's attorney, Michael Laurato, said last week. "If it wasn't for his criminal record, he kind of didn't exist."

Arnold Levine, another attorney who represented Ford in the suit, remembers Shakespeare as an "angry guy" whose post-Lotto loans and gifts came with "strings attached."

"My sense," Levine said last week, "was that some of his family members were unhappy with the amount of money he had parceled out to them.

"Were there people who were jealous? I would assume so."

Shakespeare said in his deposition before the trial that he never stole anything from Ford.

"He knows the truth," Shakespeare said. "I know the truth."

He detailed some of his gifts — "the Bible states it's better to give than to receive," he explained — and he told attorneys about some of the women who had been living with him in his new Red Hawk home. He mentioned three. He knew the last name of only one.

"I don't try to get to know nobody's last names," he said.

At the trial, according to Laurato, Shakespeare came to court hauling a garbage bag stuffed with thousands of lottery tickets he said he had purchased over the years.

The jury sided with Shakespeare. But the appeal process dragged on.

The first time Shakespeare met with Jim Valenti, his appellate attorney, Valenti said last week, there were 10 people in the room.

"Advisers? Friends?" he said. "I'm not sure who they all were."

Valenti wouldn't say how much of Shakespeare's lottery winnings were left by then, but he did say it was "really sad."

"I'm not sure by whom, but I think he'd been taken advantage of," the attorney said. "He was a man who was very weary by the time he got to me. I wonder if Abraham wouldn't say he would like to go back to the day before he won that money."

The last appeals hearing was May 27. Shakespeare didn't show.

• • •

Family and friends haven't seen him since April. They called the Polk Sheriff's Office last month to report him missing.

The other day at the Super Choice meat market here on W Memorial Boulevard, one of Shakespeare's old regular hangouts, two signs with his picture and information were taped to the windows.

He's 6 feet 5. He's 190 pounds. He has black hair and brown eyes.

CALL 1-800-226-TIPS.

Reward: $5,000.

Authorities won't say how many tips have come in. All they'll say is that none has led them to him. If he's hiding and wants to stay that way, they say, they'll let him be — as long as they can confirm that he's okay.

Until then, though, his disappearance is "suspicious" and homicide is a "possibility," Judd, the sheriff, said last week.

"We want information leading us to Abraham Shakespeare, dead or alive," Judd said. "Someone somewhere knows something."

In front of the Super Choice, Eddie Dixon, with a black cap on his head and gold teeth in his mouth, pointed at a sign.

"Only thing I know is that's my best friend," he said. "Y'all need to go ask that white woman where that man at."

• • •

The "white woman" is DeeDee Moore, who sometimes goes by Dorice Moore, or Dorice Donegan, which is her maiden name.

She's 37. She's living in Shakespeare's house behind the fence behind the gate because she owns it. Or at least her company does. It's a medical staffing outfit in Plant City called American Medical Professionals, which now owns all of Shakespeare's various real estate holdings and other assets, too.

She told the Ledger newspaper in Lakeland last week that she helped him disappear. That's what he wanted, she said, because he was falling behind on child support again — a second son born a little more than a year ago to a much younger woman — and because he was so tired of people continuing to bug him for money he no longer had.

"He intentionally did not want to be found," she told the paper. "He didn't care what it took."

Moore met Shakespeare barely more than a year ago.

It started at an annual small-business conference in November 2008 in Kissimmee. That's where Moore met Barbara Jackson. Jackson was the Realtor who had sold Shakespeare his house on Red Hawk Bend.

"When I met her, she was in a wheelchair," Jackson said last week. Moore said she had been in a car accident. "She wheeled up right beside me."

Moore was part of a group of people Jackson told about Shakespeare and how he had changed her views about money. "It's not about money at all," Jackson said. "It's about helping people."

Moore told Jackson she was a writer and that she wanted to do a story on her and Shakespeare. Maybe even a book. Jackson set up a meeting. The three of them got together in Lakeland.

"When she came to the house," Jackson said, "she jumped out of a Hummer, walking. And she was on heels. She said she healed herself through scuba therapy. It wasn't even two weeks."

Here are some of the things Moore has done since then:

• On Jan. 9, she bought Shakespeare's house, the one he had bought for $1.1 million, for $655,000.

• On Feb. 9, she became the primary manager of Abraham Shakespeare LLC, taking over his affairs and buying the debts people owed him, meaning the people who owed Shakespeare money - eight people, almost $600,000 - now owe that money to her.

• On Feb. 13, she got divorced, ending a 17-year marriage to a man with a fill dirt company.

And here is something she did back in 2001:

She drove the new $36,000 Lincoln Navigator on which she owed $46,000 and parked it in a garage in Pasco County. She got an accomplice to tie her up, take her to Wimauma and throw her in a ditch. Then she told a passer-by who stopped to help that she had been raped at gunpoint by three Hispanic men who stole her Navigator.

She was convicted of insurance fraud and falsely reporting a crime. She got a year of probation.

Earlier this fall, as rumors about Shakespeare's disappearance began to circulate around Lakeland, she told three different Ledger reporters that she could set up an interview with him. It never happened. She told Shakespeare's mother she could set up a meeting with him. It never happened.

Sheriff's detectives, she tearfully told the paper, have questioned her and searched her home, her Hummer and her hard drive. They've given her a lie-detector test and checked for blood.

"I'm not going to be O.J. Simpson and run," she said.

Shakespeare's mother, Elizabeth Walker, who works in the cafeteria at Florida Southern College and didn't return phone messages left last week, told the Ledger last month that she didn't know what to think, about Moore, or about her son and where he might be.

Moore gave the paper a video she took of Shakespeare earlier this year.

As Shakespeare appears to scroll through images taken by the surveillance cameras in his house, Moore asks if he gets tired of people asking him for money.

"They don't take no for an answer," he says.

She asks him where he wants to go.

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

California? Cozumel? A foreign country? She asks him if he's going to miss his home. He seems annoyed with her. He motions for her to turn off the camera.

"I might miss it," he says, finally, "but life goes on."

• • •

It doesn't make sense, say those who know Shakespeare. He showed up at Super Choice every day. He sometimes went on trips but always came back.

"It would be amazing to me if he just up and left," his friend George Massey said.

Shakespeare, he said, wasn't tired of people asking for money.

"Abraham thrived on that," he said. "He went from a nobody to somebody of importance — you know, in demand ..."

Here's a demand: He has a child support court date on Jan. 10.

• • •

One recent evening no one answered the doorbell at 9340 Red Hawk Bend Drive. No one answered knocks. In the long driveway were a shiny silver Chevy pickup and a shiny black Corvette. On the front porch with the tall pillars and the ornamental lions were two mats at the base of the door.

One read BLESS THIS HOME. The other read GO AWAY.

Times researchers Shirl Kennedy and John Martin contributed to this report.


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