4 Lottery Tickets That Brought Crime and Misery

4 The Murdered Truck Driver’s Assistant

When Abraham Lee Shakespeare won the lottery in 2006, his first problem was proving he’d really won it at all. According to Shakespeare — okay, hold on a sec. It’s going to be crazy calling this guy Shakespeare for the remainder of this article. For the sake of smoothing your own reading experience, we will refer to him exclusively as Abraham going forward. Which is still a bit of a mouthful, and is also a name you associate with a figure from history, but it’s not a mouthful name that you exclusively associate with one man from history, so Abraham it is. 

According to Abraham, a friend named Mike Ford bought the ticket for him. Ford did this when the two stopped at a convenience store during their job making food deliveries for $8 an hour. It was Abe’s money, and was bought on Abe’s instruction, so it was Abe’s ticket, though Ford physically bought it. According to Ford, however, Ford bought the ticket outright, then Abe stole it out of his wallet. If Ford’s version were true, it sounds like he should have demanded the entire $17 million lump sum Abe received, but he only asked for $1 million. A jury listened to the case, believed Abraham and awarded Ford nothing.

That was just Abraham’s first taste of how acquaintances would all want a share of his winnings. After buying himself a house and car and not much else, Abe now bent to the requests of family and friends, paying off all their mortgages, and sealing away a million dollars each for his stepfather and son. Which was cool of him, but this meant he was soon down to his last million. With financial planning, that might be enough to retire on, but without, it could vanish and leave him one of those proverbial winners who lose it all. Fortunately, assistance came from someone new he met, Dorice Moore. “Dee Dee” Moore first said she was writing a book on him and then offered her expertise to help him manage his money. 

Moore wasn’t really a business manager, or a writer. She worked in sales, including multi-level marketing. From these jobs, she claimed an income far beyond what she actually earned. She claimed this inflated income to qualify for auto loans, which she fell behind on paying back. As for her one legitimate sales job, that company banned her from selling their stuff, pending a fraud investigation.

Then there was the issue of the carjacking. In 2001, Moore said two Mexican men kidnapped her, raped her in her car, dumped her in a ditch and drove off. She submitted to a full rape exam, including detectives taking fingernail scrapings and keeping all the clothes and underwear she had on as evidence, which was a surprising choice, as she hadn’t been raped and had in fact made up the whole story. This was all a scheme to falsely report her car as stolen, so she could keep it without repaying her loan. She pleaded guilty to a misdemeanor and got a year’s probation. 

Moore created a company called Abraham Shakespeare LLC to manage Abe’s fortune. This gave her control over all his remaining money as well as possession of his house. Then, after April 2009, Abe's family stopped seeing the man. They did continue to receive texts from him, but this communication just made them worry more. For one thing, the texts never sounded like him and were unable to answer any personal questions. For another, Abraham was illiterate, which generally does not translate to favoring texting over calling.

Early in 2010, someone tipped off the police and told them to check the backyard of Moore’s boyfriend. There, they found Abraham’s body under a concrete slab. Moore had till now been insisting that the man was alive and well in Texas (or Jamaica, or Puerto Rico, depending on what story she was offering that day). Now, confronted by police, she said she was aware of the man’s murder but had not committed it herself. Drug dealers had killed him. Or, she alternatively claimed, her own 14-year-old son had killed him. In the end, prosecutors successfully got a conviction against Moore for first-degree murder. 

Last year, Florida (where this whole story took place) passed a law preserving the anonymity of lottery winners. One person who endorsed the law? Dee Dee Moore. Winning the lottery makes you a target, she said from prison, where she’s serving a life sentence with no chance of parole. 

3 The Stolen, Frozen Ticket

Our next lottery winner was another low-earner whose whole life could change radically with a sudden windfall. Robert Miles worked maintenance at an apartment complex, and when he bought a scratch-off ticket worth $5 million in 2006, he was high on crack. The clerk at the New York store that sold the ticket therefore chose to tell him he’d won just $5,000, not $5 million. Out of that, $1,000 was the store’s share, claimed clerk Andy Ashkar. So, Ashkar gave Miles $4,000, then locked the door on him to keep him from coming back in.

Miles woke with four grand the next day, which isn’t the worst way to start your morning. Still, his mind was clearer now, and he realized that ticket of his had been worth millions. Could he fight to get that money? No, he figured. The ticket no longer remained in his possession, so he had zero way of proving it had ever been his. If he went to the lottery organizers, or the police, surely they’d dismiss his claims as the ravings of a crackhead. Maybe they’d find an excuse to confiscate what little money Ashkar had given him.

The next few years weren’t great for Miles. The $4,000 wasn’t a life-changing amount of money, and he filed for bankruptcy. As for Ashkar, he held on to that winning lottery ticket without cashing it in, all the way till 2012. That either shows an astounding level of self-control or betrays just how little he needed a win, compared to Miles. Besides the convenience store, which was a family business, Ashkar had a six-figure income from an auto dealership. 

When Ashkar finally did show up at lotto headquarters to claim the money, everyone there had some reasonable suspicions. Who in the world waits over five years to get $5 million? Ashkar claimed he had a good excuse: He’d “had a lot going on.” Ashkar asked to receive the money anonymously — which is often a justifiable choice, as we’ve established, but in exchange for this anonymity, he offered to give up a portion of his winnings, which sounded like he was a little too keen on secrecy. Most suspicious of all, he’d bought this ticket at the store that he himself ran. That’s not normally how this works. 

Lottery officials put out a press release, and the report found its way to Robert Miles. He now had the confidence to go police and plead his case. It helped a little that, despite not getting his millions back in 2006, he’d cleaned up a bit and showed up at the station having first indulged in no crack at all. Authorities investigated, and it all ended in 2013 with Ashkar sentenced to 8-to-25 years in prison, with other charges for family members who may or may not have had a hand in the plot. As for Miles, he actually did get his $5 million payout. It was seven years late, but he got it. 

2 The Time Travel Ticket

The person who sells tickets is always in a slightly different position from anyone else when it comes to winning the lottery. This proved even truer than usual in China in 2006, when a seller named Zhao Liqun learned that his role running lottery stalls let him personally continue to buy tickets for a few minutes after the winning numbers were announced. He could wait to hear the number and then select a ticket accordingly and win. 

This sounds like an insane flaw in the system, but there are reasons China didn’t notice it earlier. This game — the Fucai 3D game in the China Welfare Lottery — is pretty low-stakes. Today, a ticket costs 30 cents, and a winning ticket gets you about $150. There are only 1,000 numbers total to choose from. You have a pretty good chance of winning, as lotteries go (though, the odds still say every dollar you bet will lead to a 50-cent loss). Every drawing produces many winners, and even if someone did manage to game the system and cheat their way to a winning ticket, it wouldn’t make a huge difference in their life, and it would make an even smaller difference in the lottery’s finances. 

Zhao Liqun did not settle on giving himself just one win, however. Once he realized he had the power to pick winning tickets, he did so again and again. Over time, he racked up $3.76 million this way, which meant he chose not just one winning ticket or dozens of winning tickets but tens of thousands of winning tickets. 

Authorities were sure to notice anyone winning that much, especially if it’s someone who sells lottery tickets for a living. For that reason, Zhao recruited friends and family to cash out the tickets on his behalf. But unless this guy was extremely popular and had thousands of people helping him, each confederate was still winning hundreds of times and arousing suspicion in the process. 

China arrested Zhao in January 2007. His punishment? Life in prison. In a lot of countries, you might even be able to commit your first murder without getting life in prison, so long as you’re not too obnoxious about it, but Zhao got life in prison for his fraud. The state also confiscated all his property — not just his ill-gotten winnings but all his property. Most places don’t do that no matter what crime you commit, but again, this is China we’re talking about.

1 The Cocaine Money Grab

Speaking of questionable confiscation, let’s look at the sad case of Jose Luis Betancourt. In December 2002, Betancourt won the Texas lottery. That netted him $5.5 million in exchange for a $1 ticket, wired right to his account. But in the days during which that transfer went through, U.S. Customs had an informant talk to him, recording the conversation. They’d already had an investigation going, but looking at the timeline here, we can’t help but think his lotto win might have had something to do with this move.

The next day, agents showed up at his house. He consented to a search, either because he didn’t understand he could refuse, because he was bowing to the inevitable or because he was really high. The agents found 1.5 kilos of cocaine on the premises and evidence that he was selling even more. He hadn’t bought the cocaine with his winnings. This was an operation he’d been running for a long time and was still continuing. 

Betancourt’s drug dealing added up to so many different offenses that he got over 20 years in prison. That would leave him up for release not too long from now, but he won’t have those $5 million waiting for him when he gets out. The government seized that money, not as a punishment but because they argued that it was proceeds from his criminal activity. Betancourt argued otherwise — that was money he’d won, not drug revenues. In fact, the money that bought the ticket hadn’t even come from his drug sales, since a neighbor had bought the ticket with their own money and then Betancourt had reimbursed the neighbor afterward. Those pleas convinced no one, and a court upheld the $5,481,462.91 forfeiture.

You might imagine that, upon winning that huge payout, Betancourt should have immediately ceased his cocaine operation, as he’d already landed upon a fortune. He did not do that, maybe because the money wasn’t enough for him and he sought even more. The acquisition of riches can be quite addictive, addictive like cocaine. Plus, you know what else is addictive like cocaine? Cocaine. 

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