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True crime. Casually done.

The Unfortunate Tale of Abraham Shakespeare: Never Win the Lottery

A wise man once said that America looks at Florida the same way that the rest of the world looks at America (with a mix of horror and fascination, that is). Whenever you hear a particularly weird or wonderful crime story, there’s a solid chance it took place in the Sunshine State. Such is the case with the story of Abraham Shakespeare (no relation), whose untimely demise was proof that getting rich isn’t always everything it’s cut out to be.


The beginning of the story is every working person’s dream. In the bizarrely-named town of Frostproof, on November 15th 2006, Mr Shakespeare and his workmate Michael Ford stopped off for a rest before heading onwards to Miami. Shakespeare asked Ford to grab him a couple of lottery tickets from a convenience store, one of which ended up winning him the statewide jackpot of 30 million dollars.

It amounted to around just 17 million after tax, but Abraham wasn’t complaining. Up until that point in his life, he had been working as a laborer and barely making ends meet. But now, at 40 years old, he was all set up for a retirement beyond his wildest dreams. That was, of course, after he dealt with the question or organizing and distributing his newfound pile of wealth among his loved ones.

Obviously his close family, kids, and best friends were in for a happy holiday season, but soon everyone he had ever met was gunning for a slice. That’s the thing when everyone hears you’ve won 30 million dollars; suddenly every little favor they’ve ever done for you has a hefty price tag attached. Even total strangers, who had seen pictures of the lucky winner in the paper, started harassing him for a cut of the winnings.

And things would only go downhill from there…


The first major blow to Abraham’s peace of mind was the underhand maneuvers of Ford, who demanded that the act of walking into the store and buying the tickets warranted a 1 million share of the winnings. I mean, his part in the whole thing was about 5 minutes of work, so at the US minimum wage of $7.25 an hour I put his actual dues closer to 60 cents.

Abraham likewise scoffed at the 1 million demand, which caused Ford to launch a lawsuit claiming that the lottery tickets were actually his, and Abraham stole them from his wallet. The story was obviously nonsense, and 17 million dollars could buy some damn good lawyers to prove it. So the case was thrown out as fast as it was dreamed up, with just one hour of jury deliberation.

But the lasting damage on Shakespeare’s faith in humanity was severe, only compounded by the constant hounding and guilt tripping he dealt with daily. To catch a breather from the cold callers, he had moved to a gated community. With all that drama to deal with, he didn’t have too much time to enjoy his winnings, so this new house, a car, and a second-hand Rolex watch were his only big purchases within the first few months.

But that had dramatically changed by the time late 2008 rolled around. By this point there was only around $1.3 million dollars left in his bank account, and Abraham was in desperate need of some solid advice on what to do next…


Enter Dorice Moore — Dee Dee to her friends. She contacted Shakespeare in 2008, saying that she wanted to write a book about his unlikely story. When they met, she offered to be his financial advisor, and to help him set up a firm with which to manage the remaining money. This was the unimaginatively-named Abraham Shakespeare LLC, of which devious Dee Dee was chief financial officer.

Why do I call her devious? Well, in case you haven’t guessed already, her motives weren’t exactly pure. Shakespeare had trusted Dee Dee, because she explicitly explained she wasn’t trying to get at his money like all those other randoms ringing his phone. But in reality, she was just much better at hiding it than they were.

This was a woman who, unbeknownst to Abraham, had been convicted of fraud in 2001 for faking a rape and kidnapping to claim the insurance money on her car — a seasoned liar. So instead of making up some lame story about her sick aunt’s medical bills, she had truly conned her way into Shakespeare’s inner circle, and gained full control of his rapidly dwindling funds.

Within 7 months of meeting her mark, she had run up a total bill of around $1 million in personal spending, mostly on cars and vacations. On top of that, she had transferred almost all of his property to her own company, leaving him very nearly broke…


We now find ourselves well into 2009, fast approaching the 3rd anniversary of Shakespeare’s big win. It’s hardly a cause for celebration though — in fact, he still feels that getting rich has ruined so much of his life, and left him feeling exploited and used.

So he’s had enough. He takes off to Jamaica to escape from it all, and enjoy his remaining wealth with the added bonus of anonymity. Or was it Texas? Or Puerto Rico? Nobody knew for sure, because Dee Dee couldn’t quite get her story straight on where her friend and benefactor had disappeared to.

On November 9th, his cousin decided to formally file a missing person’s report, on account of the fact that they hadn’t actually seen him in person since April. Sure, they had spoken to him by text, and even received birthday cards from him, but… something was off.

The texts, for example: Shakespeare was suddenly writing a lot more eloquently than he ever had before — strange for a guy with a very limited education. And when they asked certain questions — ones which relied on personal information only Abraham would know — the messages would simply go unanswered. It was almost as if they were speaking to a different person entirely…


So it’s little wonder why Abraham’s family were worried. And that wasn’t the only clue. In the months after he was officially declared missing, Abraham’s mother received handwritten letters from him (despite the fact he couldn’t write), as well as phone calls from someone claiming to be him (despite having a different voice).

Naturally, their suspicions fell upon the woman who would have most benefited from Abraham’s timely disappearance. As suspicion started to be heaped upon Dee Dee, she started making some pretty strange offers to various people involved. For example, she tried to pay $200,000 to one of Abraham’s ex partners, and mother to one of his kids, to tell investigators she had seen him recently.

Likewise, the birthday card to his mother had been sent because she paid a family member $5k to say Abraham passed it along. If all of this wasn’t incriminating enough, what came next would put the whole thing beyond any doubt…


In late December, the detectives working the missing person’s case eventually found their way to the doorstep of a man named Gregory Smith. He was a so-called friend of Shakespeare, and it turned out he was the impersonator who had been making the calls to dupe his worried mother.

Rather than wade deeper into the deception, Smith agreed to side with the police. Not long after, he received a call from Dee Dee offering $50,000 if he would take responsibility for what she had done. He agreed, and asked where Abraham really was now…

With that information in hand, the investigators went to a home recently bought by Dee Dee. They removed a heavy concrete slab in the garden, and started digging. What they found was, of course, the remains of Abraham Shakespeare. Analysis revealed that he had died way back at the start of April 09, not long after the last time he saw his loved ones.

Dee Dee Moore’s account of how he ended up there followed her usual scatterbrained pattern of making up half a dozen stories and choosing them all one after the other. These included blaming her teenaged son, blaming some imaginary drug dealers, and eventually blaming Abraham by saying she killed him in self defense.

In reality, she had shot him through the chest with a 38 caliber revolver, in cold blood, and attempted to cover her trail by keeping his digital ghost alive, and offering cash rewards for anyone willing to help maintain the lie. And can we address the amount she offered before going any further — $50k is a bit stingy for someone looking at a guaranteed life sentence!

And that’s exactly what she ended up getting. She was picked up by police on February 2nd 2010, and held with her bail set at $1 million. Around 18 months later, she was handed life without parole, plus a 25-year cherry on top for using a gun in the act.


That sounds like justice served to me; a tidy resolution to a tragic story. It’s difficult to find any sympathy for someone so predatory as Dee Dee Moore — someone who took advantage of Abraham’s need to find someone, anyone, who he could trust.

Winning the lottery had shown him the worst parts of human nature, and made it nigh on impossible to tell true friends from parasites. Getting rich hadn’t brought happiness — it had brought only pain and tragedy. The final kick in the teeth was that, by the time his killer shot him down, Abraham had only around $14,000 left.

So the moral of the story is, don’t get rich. Seriously, if any of you come into an unexpected lump sum of cash, I’ll take it off your hands. I wouldn’t want to see you through all that.

I take PayPal.

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