$30M Florida lottery winner handed out cash during his problem-filled life

Fla. lottery winner led problem-filled life

LAKELAND, Fla. — When Abraham Shakespeare cashed in a $30 million Florida Lottery ticket in 2006, the barely literate ex-con posed for a photo with a giant oversized check.

He promised the money wouldn’t change him. Three years later, his body was found under a 30-by-30 concrete slab behind a friend’s home.

That friend — Dorice “DeeDee” Moore — has been called a “con artist” by police. She’s also been charged as an accessory to Shakespeare’s murder, but she says she didn’t kill him. No one else has been arrested.

While the details of the slaying are still a mystery, how Shakespeare squandered his wealth is not.

Shakespeare started handing out wads of cash days after he won the lottery, according to court documents from Polk County, where the 43-year-old was born and lived a problem-filled life.

When Shakespeare was 13, he was arrested for stealing from a convenience store. He was freed from a juvenile reform school at age 18.

Over the next decade, he was arrested for everything from trespassing to assaulting his girlfriend, which landed him in prison. He was released in 1995 and went to live with his mother.

Shakespeare then worked odd jobs, everything from garbage collector to dishwasher. He was fired from many positions and quit others. In one court document, he tried to explain why.

“I woke up one day with some money in my pocket and turned over and I said, I ain’t going to work and I just quit. Young, wild and foolish.”

He had another girlfriend, and they had a son — but they broke up and the relationship devolved into a flurry of restraining orders. Police arrested him in October 2006 because Shakespeare was behind some $6,000 on child support.

Upon getting out of jail, Shakespeare went back to his job as an assistant truck driver — an $8-an-hour gig that entailed unloading boxes from a tractor-trailer at fast-food restaurants.

Less than a month after being released, the truck’s driver, Michael Ford, stopped at a convenience store in a tiny Florida town called Frostproof, on the way to a delivery in Miami. He went inside to buy a soda, and asked Shakespeare if he wanted anything.

Shakespeare had $5 in his wallet. He took $2 and handed it to Ford. “Can you get me two quick picks?” he asked.

That was on Wednesday, Nov. 15. By Friday, Shakespeare was in Tallahassee, holding the big check.

The first sign of trouble came the next day, when Ford showed up at Shakespeare’s home. Was it possible that Shakespeare could give him some money?

Shakespeare took the lump sum rather than $1.5 million a year for two decades. Less than a week later, the man who had never had a bank account before winning received about $17 million.

In those last weeks of November 2006, Shakespeare was like the Santa Claus of Lakeland. He gave one man $5,000. Another man, a $10,000 loan. To his stepsisters, $250,000 each. To his stepfather, $1 million.

That friends, family and strangers took advantage of Shakespeare is no surprise to people who counsel lottery winners.

“Nine out of 10 people don’t handle it well,” said Don McNay, a Kentucky-based writer and financial adviser who has written books and columns on lottery winner horror stories. “It’s life-changing. If you have a bad habit, it makes it worse. Addiction problems get magnified. People think that money cures problems, but it really magnifies them.”

Shakespeare bought a $1.1 million house for himself, paid off the mortgages of two friends who were nearing foreclosure and buried five people — most of them he didn’t even know personally.

Shakespeare’s former co-worker, the truck driver, sued him, claiming he actually had bought the winning ticket and that Shakespeare had stolen it from his wallet. A judge ruled in Shakespeare’s favor, but not before he spent lots of money on legal fees.

The state of Florida took $6,000 for back child support. Shakespeare set up an account for his son, and put a million dollars in it.

“I can’t count the people I gave money to, thousands of dollars,” he told the lawyers in a deposition for the Ford lawsuit.

A woman named Darlene moved in with him, then moved out, replaced by a girl in her twenties named Tori. Shakespeare didn’t know her last name.

“I wouldn’t know that,” Shakespeare said in the court deposition during the lottery ticket dispute. “We wasn’t too long got together.”

There were more lawsuits and more brushes with the law.

An ex-girlfriend sued for $5,000, saying that he had given her a truck, then took it away. The woman named Tori claimed her baby was his, and sued him for child support.

“His life was miserable,” said Elizabeth Walker, Shakespeare’s mother. “He couldn’t say no. He didn’t get any peace.”

In 2007 alone, Shakespeare was stopped by police five times for everything from driving without a license to not wearing a seat belt — and twice sent to the Polk County jail for those driving infractions. Before winning, he didn’t have a license. After he won, he bought a $100,000 BMW and a truck.

And then he met “DeeDee” Moore, a heavyset, bleached-blonde woman with a criminal record. She said she wanted to write a book about Shakespeare’s life.

Moore was sentenced to a year of probation after she was charged with falsely reporting that she was carjacked and raped in 2001. Officials said she concocted the insurance fraud scheme to collect money for the “stolen” SUV.

Shakespeare trusted Moore, and her company bought properties he owned, including Shakespeare’s home for $655,000 in January 2009. Three months later, detectives said he was killed and buried in the back of Moore’s home.