Michael LaPointe’s monthly column, Dice Roll, focuses on the art of the gamble, one famous gambler at a time.
When investigators smashed through the concrete slab, they found his body six feet deep, laid out on a bloodstained towel. In a black jacket, shoeless, his hair in a stocking cap, he was partially mummified, embedded in lime. The detectives knew they were looking at the remains of Abraham Shakespeare.
It was January 28, 2010, and Shakespeare had been missing for nine months. Rumors had swirled all through the Lakeland area, in central Florida. Some said he’d split town, tired of the constant requests for money, others that he was hiding from the woman who was his ex-girlfriend and the mother of his child. But after months of no one hearing from him, it was clear that something was terribly wrong.
Now, the detectives discovered he’d been shot and buried in a yard on State Road 60. What exactly had happened remained a mystery, but everyone knew it began with these numbers: 6, 12, 13, 34, 42, 52.
On the night of November 15, 2006, Abraham Shakespeare was happy to be working. He had five bucks to his name, no bank account, no credit card. He didn’t have a driver’s license, either, so he couldn’t operate the truck in which the MBM Corporation had sent him and a coworker, Michael Ford, to deliver meat to fast food restaurants from Lakeland to Miami. But every hour on the road meant another eight dollars. It was a meager living, but it was a living.
In Frostproof, Ford pulled into a Town Star convenience store and asked if Shakespeare wanted anything.
“Get me two quick picks,” he said.
With his very last dollars, he’d play the Florida Lottery. The jackpot that night was $31 million.
What possesses someone to play the lottery, when he’s never caught a lucky break? Many might say ignorance, but a 2008 study in the Journal of Behavioral Decision Making shows how mistaken that would be. Participants of an experiment were asked to consider whether rich, middle class, or poor people have better odds of attaining various outcomes, such as being elected mayor, becoming a superstar singer, or receiving a promotion. Then they were given an opportunity to purchase lottery tickets. Compared to a control group, those who’d been asked to consider the relative advantages of different classes were more likely to play the lottery. The authors concluded that low-income individuals “are likely to perceive the lottery as a rare opportunity to compete on equal footing with people who are more affluent.” In a culture that showers benefits upon the already advantaged, a game of chance seems like the only thing that doesn’t discriminate.
Just as lottery play tracks along class lines, so does it have a racial skew. A study of the Virginia lottery showed that 61 percent of its sales are made to just 8 percent of the total population, and more than one in three of that very small slice are Black. It remains an open question whether lotteries intensify marketing campaigns in Black communities—and how effective such campaigns would be—but it’s indisputable that the business would crumble without players like Abraham Shakespeare.
It could never be said that he was among the advantaged. Born in Sebring, Florida, in 1966, Shakespeare dropped out of school after seventh grade, and was incarcerated in a state-run juvenile detention facility from the age of thirteen to eighteen. He was never taught to read or write. Afterward, like many formerly incarcerated people, he couldn’t regain his footing. For much of his life, he struggled to stay afloat.
But everything changed for Shakespeare with the bounce of a numerized ball. His quick-pick ticket hit the jackpot. All at once, he was rich.
Lottery winners are advised to remain anonymous and secure the services of a lawyer before presenting themselves, but Shakespeare casually appeared on TV from Tallahassee, holding an oversized check in a Florida Lottery T-shirt. This unlikely millionaire couldn’t have been a better advertisement for the lottery: a day laborer down to his last dollar, suddenly rocketing to exorbitant wealth. No matter how bad things get, Shakespeare’s face seemed to say, don’t despair. Today could be your lucky day.
Casting lots has always seemed the most democratic of gambles. Flip a coin, odd man out, rock paper scissors—there’s no skill, no advantage, we’re all in this together. Chance is oddly consoling. If an outcome appears random, then whether it’s good or bad, we can tell ourselves that no was one responsible, it’s just our luck, c’est la vie. But while the modern lottery depends on people’s perceiving it as a purveyor of dumb luck, just a random generator of breaks, its one-in-a-million winner is only one side of the equation. For those on the other side—those who control the lottery—it’s a guaranteed jackpot every time.
Critics of the lottery have always agreed with Honoré de Balzac, who once called it “the opium of the poor,” a tax exacted from those who, in his words, “work up magical hopes.” Balzac was responding to a culture of state-sponsored lotteries that, beginning in the fifteenth century, were held to collect funds for public works, like city walls. As private wealth ballooned under nascent capitalism, comparatively poor governments found they could keep pace by running lotteries.
As time went on, the tax on hope became indispensable to statecraft. Indeed, the British lottery was so instrumental in funding colonization that Gerda Reith, in The Age of Chance: Gambling in Western Culture (1999), calls the colonies the public work of the lottery par excellence: “It can be said that the first American settlement of Jamestown was almost entirely funded by British gamblers playing the lottery.”
Yet it would take time for lotteries to become the fixture in American life that they are today. The Louisiana Lottery is largely responsible for slowing things down. Initiated in 1868 to fund a hospital in New Orleans, the Louisiana Lottery quickly spiraled out of control, with draws running daily and millions of tickets being sold all across the country, earning it the nickname the Serpent. In Roll the Bones: The History of Gambling (2006), David G. Schwartz writes that by the 1880s, over half of the New Orleans Post Office’s mail was related to the lottery. Corrupt politicians drew freely from the funds, inspiring such outrage that not only was the Louisiana Lottery disbanded, it would be almost seventy years before any legal lottery operated again in America.
That all changed in 1964, when New Hampshire started up a modest lottery to compensate for the state’s lack of sales or income tax. Memories of the Serpent had faded, and sensing that the national attitude had shifted, New York and New Jersey got in on the action. State lotteries began emerging just about everywhere, and today, they’re operational in forty-four states.
The Florida Lottery was founded in 1988. With an annual revenue of nearly $7 billion, its purported aim is to enhance education in the state; the lottery funds scholarship programs and helps reduce class sizes. But, critics claim, in a state without income tax, the lottery doesn’t enhance education so much as it replaces shortfalls in a budget that constantly shrinks. Before the advent of the lottery, the state funded 61 percent of education; today, its share is 52 percent.
Because those who buy tickets are, like Abraham Shakespeare, disproportionately lower income and Black, the lottery has shunted the burden of taxation onto the vulnerable, who do not receive a proportionate share when the funds get doled back out. The lottery effectively functions as a massive enterprise of wealth extraction and redistribution. We’re all in this together? Far from it.
At a central Florida business conference in 2008, a real estate agent told the story of someone to whom she’d sold a house on Redhawk Bend. His name was Abraham Shakespeare, he was illiterate and previously homeless, and he’d won the Florida Lottery. Yet all he did was give his winnings away. “It’s not about money at all,” the agent said. “It’s about helping people.”
“I don’t have to struggle no more,” Shakespeare had declared when he collected his winnings (he’d won $31 million, but like most lottery winners, had opted to take a lump sum—about $17 million, minus 25 percent in taxes—rather than an incremental payout of the total). And as long as he could help it, the people around him wouldn’t have to struggle, either. Just as the lottery burdens poor communities with funding state services, so Abraham had found his social safety net in local businesses, where community members would look out for him. The owner of a barbershop, for instance, gave Abraham little tasks to perform, remembering how his grandfather would offer chores to men in similar positions, believing that money for honest work would prevent crime in the community.
But now that he’d hit, Shakespeare remembered those who’d been good to him, and repaid every little kindness with considerable interest. He paid for people’s medical bills, utility bills, funeral bills. He loaned a friend $1 million, and gave three stepsisters $250,000 each. Someone he didn’t even know had their $60,000 mortgage paid off.
Precisely because of his generosity, Shakespeare was dismayed to learn that his white coworker on that meat run to Miami was suing him. Michael Ford claimed that the winning ticket had been his all along. He’d put it in his wallet in the glove compartment, he said, and Shakespeare—who had felony and misdemeanor convictions, Ford’s lawyers reminded the press—had stolen it from his wallet. The jackpot should be his.
Shakespeare said Ford was simply bitter. He’d asked for a million dollars and threatened to sue if he didn’t get it. “He knows the truth,” Shakespeare said. “I know the truth.”
It took the jury just over an hour to decide in Shakespeare’s favor. Still, the trial cost him another $800,000 in legal fees. Asked what he’d do, now that the ordeal was over and the money incontestably his, Shakespeare told the Tampa Tribune, “My goal is to be able to wake up in the morning, get a fishing pole and go fish.”
At that business conference, when the real estate agent finished telling the story of this humble millionaire, a white woman in a wheelchair introduced herself as a writer named Dee Dee Moore. She’d been in a car accident, she said, but still wanted to work, and Shakespeare sounded like the perfect subject for a book. She asked if the agent would arrange a meeting, and soon after, the agent got the two of them together. Shakespeare could not have a caught a more unlucky break.
“When [Moore] came to the house,” the agent recalled to the Tampa Bay Times, “she jumped out of a Hummer, walking. She said she healed herself through scuba therapy.”
The book project was soon abandoned. Moore said she’d given up writing after seeing how many people were taking advantage of Shakespeare’s generosity. She wanted to help him manage his assets, and that meant setting up an LLC under her control.
Moore passed herself off as an accomplished businesswoman, and, without the ability to read or write, it was difficult for Shakespeare to interrogate her claims. Anyway, after the lawsuit, he was looking for someone to trust. He signed over the deeds of three houses to Moore, and gave her ownership of outstanding loans that amounted to nearly $400,000. Soon she moved her son, her boyfriend, and herself into the houses. (Asked by 20/20 about what led to Shakespeare’s downfall, a friend said, “His illiteracy. His kind heart.”)
Getting control of Shakespeare’s fortune wasn’t the first of Moore’s schemes, or the most audacious. In June 2001, someone in Wimauma, Florida, found her by the side of the road with her wrists bound. As Deborah Mathis and Gregory Todd Smith write in Unlucky Number (2015), Moore claimed that “three clean-cut, tattooed Hispanic men had abducted and raped her at gunpoint, thrown her in a ditch, and stolen her car, a Lincoln Navigator.” Moore’s lies often depended on racist stereotypes, counting on her status as a white woman to garner sympathy.
But her fantasies were always rickety—“She tells the fibbiest fibs,” said her father—and her lie unraveled just days later, when a man confessed to having helped her stage the event. “Dee Dee had taped her own wrists,” write Mathis and Smith, “and, spotting a ditch along the road, had ordered him to slow down and then thrown herself from his SUV.” It turned out that a credit union was threatening to repossess her Navigator, which she’d stashed in a garage, and this charade was her way of keeping the car from collections. Moore was convicted of insurance fraud and falsely reporting a crime, and given a year’s probation.
Later, Moore would claim she’d written her book about Shakespeare after all. It was to be called One Step Closer to Crazy.
When Abraham Shakespeare went missing in the spring of 2009, signs appeared throughout Polk County: CALL 1-800-226-TIPS. Reward: $5,000. The sheriff appealed to the public for help. “Someone, somewhere, knows something,” he said.
At least on the streets of Lakeland, everybody knew who that someone was—Dee Dee Moore. Just a year after meeting Shakespeare, she was living in his house and spending his millions. Moore, for her part, told whoever would listen that Shakespeare was in hiding, and that she could talk to him whenever she wanted. “He intentionally did not want to be found,” she told the Lakeland Ledger. “He didn’t care what it took.”
Just look at the video she’d happened to take shortly before his disappearance, Moore told people. In the video, Moore interviews Shakespeare, who’s wearing a white T-shirt, dreadlocks tucked into a cap, and watching footage from the surveillance cameras of his palatial home.
“Do you get tired of people asking you for money?” she says from behind the camera, every question a leading one. “You’re just ready to start living your life, huh?”
“They don’t take no for an answer,” Shakespeare says with a shrug.
“So where you want to go to?”
“It don’t matter to me, I’m not a picky person.”
“California? Foreign country—Cozumel?”
Shakespeare seems annoyed by the camera, and signals to turn it off.
“Are you gonna miss your home?” she presses.
“If I miss it,” Shakespeare mutters. “But life goes on.”
Moore said she’d made the tape because she’d anticipated questions about his whereabouts. But then again, she said lots of things. As police began focusing their investigation on her, Moore floated other explanations. “He wanted to pretend that he was dying of AIDS so that he doesn’t have to pay child support,” she told them. When that fib didn’t catch on, she said there was a tape of him having sex with a minor, and that he’d escaped before it came to light.
Privately, Moore was spinning still wilder fantasies. In one, Shakespeare was killed by a drug dealer from Miami. In another, he’d perished in the recent earthquake in Haiti, which had killed hundreds of thousands. Unfortunately, she was concocting these lies with one of Shakespeare’s friends, who’d gained Moore’s trust while operating as a police informant. He managed to get her to admit that Shakespeare was buried in her backyard, and even got her to produce the murder weapon. Not that she’d confess to killing Shakespeare, of course—she said the murder was committed by a drug dealer from Miami, who’d then forced her to dig the hole, cover the body in lime, and hire a company to pour a thirty-by-thirty concrete slab on top.
On February 19, 2010, Moore was charged with first-degree murder. “If I tell you the truth about who killed Abraham,” she asked detectives, “can I keep my things?”
“Money was the root of the evil that you brought to Abraham,” said the judge. “Now I’m going to pronounce your sentence.”
It was December 10, 2012, and a jury had just found Dee Dee Moore guilty of the first-degree murder of Abraham Shakespeare. The defendant hadn’t exactly ingratiated herself during the trial. She’d been briefly banned from the courtroom for threatening the jurors. It’s unclear what immediately precipitated the killing, but prosecutors argued that Shakespeare had discovered she’d siphoned off hundreds of thousands of his dollars. In their narrative, faced with the prospect of exposure, Moore had shot him twice in the chest.
When the judge sentenced her to life in prison without parole, Moore blinked once in dismay, as if she’d really expected to catch a lucky break. To this day, she maintains her innocence, insisting she has evidence that will exonerate her (but refusing to produce it). “I would never hurt nobody,” she tearfully told 20/20. “I liked Mickey Mouse and Donald Duck and Disney.”
Over the course of Moore’s arrest and trial in 2012, the lottery enjoyed a banner year in America. Whatever lessons the death of Abraham Shakespeare might have imparted were ignored, his story framed not as a tragedy rooted in race and class exploitation but as just a series of bad breaks. In what the Guardian called “a sort of national hysteria,” millions of Americans in 2012 played the Mega Millions lottery, ballooning its jackpot to $640 million, the largest in American history. On a single Friday, $650 million of tickets were sold. “People stood in long lines at convenience stores,” reported CNN, “dreaming of what they’d buy, how they’d quit their jobs, and how their lives would change with the help of Lady Luck.”
Read more installments of Dice Roll here.
Michael LaPointe is a writer in Toronto. His debut novel, The Creep, will be published by Random House Canada in 2021.
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