The true crime story of murdered Florida lottery winner Abraham Shakespeare.
Poor man. Rich man. Dead man.
It sounded like a fairy tale: A homeless man named Abraham Shakespeare spent his last dollars on a Florida State lottery ticket—and miraculously won $31 million.
Unprepared for his new found fortune, Abraham hired Dorice “Dee Dee” Moore to help manage his winnings and field the numerous requests for loans and assistance that he received. But somehow, Dee Dee was the only one benefiting.
When Abraham quietly disappeared from his home in Florida, friends and family grew suspicious—though he could not read or write, his only form of contact was through odd letters and texts.
But it wasn’t until investigators began to question Dee Dee about her role in Abraham’s finances that a complicated web of lies—and the desperate lengths to which one woman would go to cover it up—was exposed…
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After working as a deadline reporter for twenty-seven years (including a seven-year stint as White House Correspondent during the Clinton years), veteran journalist and author Deborah Mathis studied under a Shorenstein Fellowship at Harvard, taught at Northwestern University’s prestigious Medill School of Journalism, was Communications Director at the Public Justice Foundation, wrote a weekly column for BlackAmericaWeb.com, and is the author of three books: Yet A Stranger: Why Black Americans Still Don’t Feel at Home, What God Can Do, and Sole Sisters: the Joys and Pains of Single Black Women.
Gregory Todd Smith is a native of Polk County, Florida. A self-made man, he enjoys a thriving barber practice in Lakeland, Florida.
ACKNOWLEDGMENTS
—DEBORAH MATHIS
PREFACE
In March 2014, on the brink of the annual college-basketball showdown known as March Madness, billionaire Warren Buffett teamed with Quicken Loans to concoct a get-rich-quick scheme to beat all. They would pay $1 billion to anyone, eighteen or older, who correctly predicted the winners of every game in the sixty-three-game national tournament. Even with the number of contestants limited (one per household) to fifteen million entries, the odds of winning were a mind-numbing one in nine quintillion. But that didn’t stop people from trying. (Unsurprisingly, no one won Buffett’s bracket contest. No one even came close. Most people were eliminated on day one; no one remained by the end of day two.)
Although Buffett’s March Madness bracket scheme was not a lottery per se, like a lottery, it was a game of chance and showed, once again, that the dream of striking it suddenly and gloriously rich is alive and well. Not even absurd, nearly impossible odds can quell it.
Lotteries have been a part of the United States since its very founding, when tickets to games of chance were sold to help fund the development of some colonies (such as Jamestown, Virginia), and at one point were considered not only a viable way to raise revenue for public causes, but a civically responsible one. At one time, all thirteen original colonies had a lottery to raise revenue for public services. But, in time, the lotteries became riddled with bribery, payout defaults, and other corruption. They fell into such disrepute that evangelical reformers were able to successfully press a moral argument for prohibition, and by 1895, government-run lotteries were banned nationwide.
The lottery’s official comeback took nearly three quarters of a century, beginning in New Hampshire in 1964. Today, armed with regulations and safeguards, forty-four states, plus the District of Columbia, Puerto Rico, and the U.S. Virgin Islands, all sponsor lotteries. Only Alabama, Alaska, Hawaii, Mississippi, Nevada, and Utah abstain.
Both religious and public policy advocates routinely oppose lotteries (the former usually due to biblical strictures, and the latter typically out of concern over the government’s reliance on fantasy-fueled games of chance to fund essential services like public education), but state and multistate lotteries are wildly popular among the masses. It is estimated that about 120 million American men and women—half of all adults in the country—play state-run lotteries each year, accounting for $45 billion in receipts. Only about 1,600 of them will win a million dollars or more. The rest of us have to settle for a few bucks, if we’re at all lucky, or more likely just add the useless slips to our pile of poor choices. The summer house in the Hamptons, the ski chalet in Saint Moritz, the foundation we were going to endow, the freedom from indebtedness, and the ability to tell the boss to take this job and shove it—all will have to live a bit longer in our fantasies and most likely will live there forever. But hope springs eternal that Fortune will make a rewarding pit stop our way. Indeed, the randomness of a lucky strike is part of the lottery’s appeal. It can happen to anyone, from any walk of life, and in even the most obscure places.
In May 2013, Gloria McKenzie, an eighty-four-year-old widow originally from rural Maine, now living in Zephyrhills, Florida, was in line at a local supermarket to buy an auto-generated Powerball ticket when the kindly young woman in front of her stepped aside, allowing Mrs. McKenzie to go first. She thanked the woman for the courtesy, bought her $2 ticket and left. Chosen at random by a machine, the ticket Mrs. McKenzie walked away with that day contained the winning numbers in the multistate lottery. Her jackpot was almost $600 million—$590,500,000, the largest in the multistate game’s twenty-one-year history and the second largest in the annals of American lotteries. By sheer luck, Mrs. McKenzie had beaten odds calculated at one in 175 million.
Like most big jackpot winners, Mrs. McKenzie elected the lump-sum option for her payday, about $371,000,000 before taxes. She sank back into obscurity after collecting her winnings in Tallahassee two months after the drawing, where she emerged accompanied by her son and two lawyers, and thus adhering to the first rule suggested by experts who study those lucky few who hit it big: get a team.
Financial planner Susan Bradley told the Palm Beach Post shortly after the big drawing that she provides the super-high-dollar clients she advises with a team of neuropsychologists, estate-planning attorneys, and other professionals to help them navigate the treacherous waters of over-the-top wealth. These teams are meant to help insulate her clients from scam artists, bad investments, tricky temptations, and the deluge of hangers-on who typically prey upon the superrich. Bradley has a special set of do’s and don’ts for the suddenly and sensationally wealthy.
“One of the first things to do is stop answering the phone,” Bradley told the newspaper. “Get a cell phone with a new number and only give it to your inner circle people and keep that circle small.”
Gloria McKenzie has apparently handled her wild fortune smartly. She is said to still shop at big-box stores and frequent neighborhood eateries, though she once paid for the meals of a restaurant full of diners. Reportedly, she has built a multimillion-dollar home in Jacksonville, Florida, but has otherwise been frugal, still tooling around “in her son’s old Ford Focus,” according to one news account.
Mrs. McKenzie’s is not the only good news story about lottery winners. There are many that end happily—or happily enough. Who doesn’t rejoice at the news that a fat jackpot has been claimed by a downtrodden single mother who rides three buses to her menial job each day? Who isn’t inspired by the Missouri couple who, after netting more than $136,000,000 from Powerball, poured loads of money into improving their town, including a new fire station, ball field, sewage-treatment plant, and a scholarship fund at their high school alma mater?
There’s also the story of Sheelah Ryan, of Florida, who used her $55 million winnings in a 1988 lottery to endow a foundation that provided assistance for poor people, single mothers, children, the elderly, and homeless animals.
But, when things go wrong for lottery winners, they can go awfully wrong. News accounts, police files, and court records are full of instances where winning was far from the panacea that most people imagine when handing over a few dollars in hopes of collecting a king’s ransom.
One of the most famous instances of good luck gone bad is that of Jack Whittaker, a West Virginian who won a $315,000,000 Powerball jackpot in 2002. The next seven years were riddled with misfortune. Whittaker was robbed several times, once to the tune of $545,000; on another occasion, he was taken for $200,000. In a three-month period, both his granddaughter and her boyfriend died of drug overdoses. And Caesar’s Palace, the legendary Las Vegas casino, sued him for $1.5 million worth of bad checks he had written to cover his gambling losses. At one point, Whittaker lamented that he hadn’t destroyed his winning ticket.
And there’s William Post, of Pennsylvania, a $16 million lottery winner. His landlady conned him out of a small fortune, his brother tried to hire a hit man to kill him, and he ended up smothered in debt.
And there’s Janite Lee, who, choosing the annual payout instead of lump sum, was collecting $620,000 a year but ended up in such straits that she sold her rights to the annual...
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