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.

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Michael LaPointe’s monthly column, Dice Roll, focuses on the art of the gamble, one famous gambler at a time.

©Ellis Rosen

In the late nineteenth century, at least according to legend, a fight to the death between a greyhound and a timber wolf was the most popular sport on the Native American reservations of South Dakota. Greyhounds had been brought to the region to help white settlers eradicate crop-eating jackrabbits, and it was said that the farmers would pit their animals against wolves captured by the local indigenous people.

Hobbling Homeward was the white man’s champion, a sixty-pound greyhound descended from a famous Irish hound named Master McGrath, whose heart was allegedly twice the size of a normal dog’s. “The Indians couldn’t believe the smaller animal could kill the fierce timber wolf,” it was said, and yet fight after fight, Hobbling Homeward prevailed.

One day, the men from the reservation claimed to have finally found a wolf who could defeat him. They staked $1,000, and “whites and Indians came for miles to see the fight,” including a young sports promoter named Owen Patrick Smith. When the wolf’s cage opened, a hideous, eighty-pound beast, “growling and snapping savagely,” leaped into the ring. A frenzy of gore ensued, “both animals scoring with their knifelike teeth,” but Hobbling Homeward managed to evade the wolf’s death-grip jaws and tore into his belly. “In less than two minutes,” the author wrote, “the great wolf lay in the arena gasping his last breath.” The greyhound was triumphant. The settlers roared.

The story, written by a sportswriter at the Miami Daily News some fifty years after the supposed event, has all the trappings of mythological etiology, like the Aeneid: the clash of civilizations, the triumph of the “civilized” bred animal, with his pristine bloodline, over the wild native—and the founding of an empire. By placing Owen Patrick Smith in the crowd that day, the author joined the writhing wolf and the blood-drenched dog to the origin of a multi-billion-dollar gambling phenomenon: greyhound racing.

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Michael LaPointe’s monthly column, Dice Roll, focuses on the art of the gamble, one famous gambler at a time. 

Original illustration © Ellis Rosen

If you could trace the fate of just one dollar that passed through the hands of John “Mushmouth” Johnson, where would it lead? It probably came to his hands off a craps table or from an office of his policy syndicate, and more likely than not, it would go on to be slipped into the pocket of some crooked cop or double-dealing politician. But if Johnson, whom local papers called “the Negro Gambling King of Chicago,” managed to hold on to it, that dollar might end up supporting a hub of black music in the twenties, or the first black-owned bank in Chicago, or a poetic precursor of the Harlem Renaissance. It would grant Johnson, in death, a respectability he was denied in life.

Johnson’s life was characterized by a constant tension between philanthropy and corruption. Born to the nurse of Mary Todd Lincoln in 1857, Johnson moved from his native Saint Louis to Chicago at an early age. Some said his nickname, Mushmouth, referred to how much he cursed. Others said it was because of a “thick utterance he had in his speech when a boy.” Either way, the name signals how Johnson’s mode of expression, coupled with his lack of formal education, cut him off from genteel society. “I didn’t exactly do much book learning,” he recalled, many years later. “I went out to see where the money grew. Some of those who know me say that I found it.”

In 1882, Johnson got a job as a porter in a white-owned gambling house. He studied the business closely, and soon opened his own nickel-gambling joint on Clark Street. Johnson had a keen eye for real estate, and quickly managed to flip that location. In 1890, he took the proceeds and purchased a saloon at 464 South State Street. He called it the Emporium. It would be the seat of his gambling empire for nearly twenty years.

Decked out in Gay Nineties style, with rococo chandeliers and a bar of Honduran mahogany, the Emporium offered three stories of action: billiards on the first floor, craps and roulette on the second, and poker on the third. In order of popularity, the bar served whiskey, gin, and beer. Scorning the day’s more flamboyant scarves, Johnson presided over the Emporium in a neat black four-in-hand knot, with a pin set with a small stone. As for that stone, one gambler said, “You can bet it’s the goods.”

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Michael LaPointe’s monthly column, Dice Roll, focuses on the art of the gamble, one famous gambler at a time. 

Original Illustration © Ellis Rosen

In April 1995, traders on the floor of the Pacific Exchange were in a frenzy. The jury in the O. J. Simpson trial had refused to come to court that morning. In the Washington Post, a law professor said that the probability of a hung jury had increased. And so at the exchange, if traders had shares in guilty or not-guilty verdicts, they wanted to dump them; a hung-jury share was looking a lot sharper today. Everyone was looking for Steve.

This had nothing to do with the stocks on the ticker, and everything to do with an elaborate, parallel marketplace operated by Steve Schillinger, an independent broker, who sold futures on the side for countless things you couldn’t find at the exchange: Who would win baseball’s MVP award? Who would make the Final Four? Would O. J. go to prison? Although Schillinger was a decent enough stockbroker, his real talent was in figuring the odds for nebulous outcomes like that of the O. J. verdict and revising them as events unfolded. His colleagues placed bets with him, and he’d pay out on the basis of whatever the odds had been at the time of the wager. He was, in short, a bookie.

“People were leaving their stocks to come bet on the NCAA,” Schillinger said, explaining why he was quietly asked to leave the exchange. But by then, he had a dream. In his covert marketplace, he’d glimpsed not just his own future, but the future of gambling. That vision would lead him to become the pioneer of a multibillion-dollar industry, and then a fugitive from justice who would die in exile.

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Michael LaPointe’s monthly column, Dice Roll, focuses on the art of the gamble, one famous gambler at a time. 

Original illustration © Ellis Rosen

Tommy saw the solution in a dream. “I’m seeing myself from behind,” he recalled, “and I have [the tool] in my hand.” All through 1990, he’d been searching for a way to cheat the latest slot machines. He needed a new tool, something to replace the clumsy old instrument that had landed him in the penitentiary. Night and day in his Vegas apartment, he toiled on a Fortune One video poker machine. But no matter what he tried, some riddle in the guts of the unit would thwart him.

Then, in the recess of sleep, the solution appeared in all its brilliant simplicity: a flexible piece of metal, wedged at the top, and some piano wire. “I woke up,” he told the History Channel, “actually got out of bed, and went and built it.” Tommy had found his answer: The Monkey Paw.

*

When a friend dropped by Ace TV Sales and Service in Tulsa, Oklahoma, in 1980, Tommy Glenn Carmichael was just an unremarkable repairman who moonlighted as a pool hustler. He had minor drug convictions and some juvenile mischief on his criminal record, but nothing about the thirty-year-old suggested that he’d one day stand among the most inventive cheats in gambling history.

Carmichael’s friend had brought along some toys to tinker with: a Bally’s slot machine and a cheating device called the top-bottom joint. Of how his multi-million-dollar criminal enterprise got started that day, Carmichael simply said, “We got to playing around.”

Triggering a payout with a top-bottom joint was a crude operation. A piece of guitar string comprised the “bottom” part of the tool. It went into the left corner of the machine, up against the circuitboard, and sent low-wattage electricity coursing through the unit. The “top” part was a piece of metal curved like the number nine. When inserted into the coin slot, it completed a circuit powerful enough to hot-wire the hopper, where the coins are kept.

Jackpot.

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Michael LaPointe’s monthly column, Dice Roll, focuses on the art of the gamble, one famous gambler at a time. 

©Ellis Rosen

“Murder! murder most foul and dastardly has been committed in our streets, and the blood of the victim crieth aloud for vengeance.”

Even regular readers of the Daily Evening Bulletin had never seen its editor, James King of William, this angry. All through the winter of 1855–56, he’d been calling for Charles Cora’s death. “He must and will be hung!” he’d written. And if the sheriff of San Francisco let Cora slip away? Then “hang him—hang the Sheriff!”

But now, Cora had been caught, and the only thing hung was the jury. Rumor had it that Cora’s lover, the madame of a Waverly Place parlor house who was known simply as Belle Cora, had influenced the jury with gold dust. Key witnesses were fleeing the city. The murder case was falling apart.

“Hung be the heavens with black!” cried King of William, quoting Shakespeare’s Henry VI, Part 1. He cursed Cora’s “obscene paramour”; he wept for “the fame of the fair city.” In the pages of his newspaper, he’d already declared war in San Francisco, “war between the prostitutes and gamblers on one side, and the virtuous and respectable on the other.” He viewed the hung jury as a patriotic humiliation.

But he wasn’t about to surrender. He ended his editorial with a threat that would’ve chilled anyone who recalled the violent excess of the Committee of Vigilance: “Gamblers, we warn you! remember Vicksburg!” Read More