Casefile True Crime: Case 248: Abraham Shakespeare

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When the winning numbers of the Florida Lottery were announced on Wednesday,

October 25, 2006, the $3 million jackpot went unclaimed. This wasn't unusual.

The odds of picking the six lucky numbers from a possible 69 was one in over $292 million.

With no claimants, the Florida Lottery jackpot rolled over,

meaning it was added to the grand prize of the next draw. Once again, nobody won.

Over the following two weeks, the jackpot rolled over three more times.

By Wednesday, November 15, 2006, it had reached $30 million.

A 41-year-old Abraham Shakespeare lived in the Florida City of Lakeland. The small home he shared

with his mother was in the same underprivileged neighbourhood where Abraham had spent most of

his life. Despite experiencing poverty, homelessness, discrimination, and run-ins with the law,

Abraham remained good-natured and easygoing. Even though he mostly kept to himself,

he was a familiar and well-liked figure in his community.

Abraham had no bank account, credit card, or savings. Dropping out of school in the seventh

grade had left him with few skills or opportunities. He was in a labour pool, a network of independent

workers that could be hired on an as-needed basis for various jobs. The tall and slender African

American took on any work available, from washing dishes and sweeping floors to collecting trash and

loading trucks. Although he spent most of his time working, Abraham Shakespeare constantly scraped

the bread line. In 2006, he was earning just $8 an hour as a truck driver's assistant for a food

distribution company. Despite his best efforts, he'd fallen behind on paying child support for

his five-year-old son. In his rare moments of respite, Abraham would walk around Lake Hollingsworth

in the city centre. He'd imagine owning one of the expensive houses that overlooked the water,

only to reflect on his current circumstances with disappointment.

On Wednesday, November 15, 2006, Abraham and a colleague named Michael Ford set out on a 230-mile

route to deliver meat to fast-food restaurants. Not long after leaving Lakeland, the pair stopped

at a convenience store in the city of Frostproof. Michael headed inside to buy drinks and cigarettes,

asking Abraham if he wanted a soda. Abraham instead told Michael to, quote,

Get me two quick picks.

Quick picks are a type of lottery ticket. The player's six numbers are randomly generated in

the lottery terminal and added to their coupon. Compared to the more traditional method where a

player personally selects each number, it's a fast and easy way to play the lottery.

Michael Ford purchased two quick picks for Abraham, and Abraham paid him two of the five dollars he

currently had to his name. He gave the remaining three dollars to a homeless man.

The Florida Lotto was drawn that night. The numbers announced were 6, 12, 13, 34, 42, and 52.

Abraham Shakespeare was stunned. He had just won 30 million dollars.

Abraham appeared on television to celebrate his massive lottery win. He was his typical

laid-back self, dressed in baggy pants and a white t-shirt with his dreadlocks tucked under his cap.

Abraham was handed an oversized novelty check with 30 million printed on it in large, bold

lettering. He had two options. Receive the prize money in annual increments of one and a half million

over 20 years, or take an immediate lump sum minus 25% in taxes.

Abraham chose the second option, as most lottery winners do, and walked away with 17 million dollars.

For Abraham, who'd only ever known poverty, that was more than enough.

As he collected his winnings, he announced, I don't have to struggle no more.

Abraham immediately used his newfound wealth to resolve several debts, including the child

support he owed. He also set up a million dollar trust for his son. Although lottery winners are

advised to seek the services of a financial advisor, Abraham didn't believe he needed one,

saying, I don't let material things run me. I'm on a tight budget.

Despite being a multimillionaire, Abraham continued to eat at his local Denny's Diner,

pick up pennies off the ground, and spend his days hanging out in his old neighborhood.

Abraham offered to buy his mother a new home, but she respectfully declined,

so he paid off her existing house instead. He then established several philanthropic

enterprises that centered on assisting those in need.

Abraham rewarded himself with just a few splurges, including a new car,

some clothes, and a Rolex watch that he bought at a discount from a pawn shop.

His biggest indulgence was a million dollar home north of the city in an upscale gated community

on Redhawk Bend Drive. The spacious two-story residence had four bedrooms and four bathrooms.

It featured stainless steel appliances, granite counters, walk-in closets,

fireplaces, a guest suite, and a double garage. French doors opened out to a private deck with

the swimming pool and spa. It was exactly the type of home Abraham had dreamed of owning.

Although Abraham's money didn't change him much, it changed everyone around him.

As soon as news of his big win got out, friends and strangers alike began approaching him with

stories of financial hardship. Described as a soft touch who thought with his heart,

Abraham willingly helped them pay everything from bills to medical treatments and business startups.

He lost count of how many people he helped, saying,

The Bible states it's better to give than to receive.

In Abraham's eyes, most of these handouts were loans rather than gifts.

Yet no one ever made any effort to pay him back. Questions about when Abraham's generosity would

be repaid were met with excuses and complaints. Some people were upset to learn his money was

given with strings attached. Conflict also arose in Abraham's family over the amount he shared with

them. Rather than making him happy, Abraham said his lottery win had made him miserable.

People constantly stopped him in the street and his cell phone rang non-stop.

During a 30-minute catch-up with his younger brother, Abraham fielded eight calls from people

requesting cash. He even received a letter from a prison inmate asking for $1,000.

While this request amused Abraham, he still sent the man $50.

Abraham's sister said he was too sweet-natured to say no to anybody,

and because of his limitless charity, Abraham never had any peace.

Both exasperated by his instant celebrity and demoralized by everyone's demands,

he began sleeping all day and cruising the quiet streets of Lakeland at night.

Abraham also escaped by traveling. He went on a cruise to the Caribbean and took a few short trips

to New York City, which he grew particularly fond of. He hoped the distance from his community

would lessen the pressure, expectations, and hostilities thrust upon him.

Michael Ford was bitter towards his former colleague, Abraham Shakespeare.

Michael frequently visited the Frostproof convenience store where the winning lottery ticket was

purchased. Without fail, he always bought two quick picks for himself.

Michael asserted that Wednesday, November 16, 2006, was no different.

Store records and CCTV footage confirmed that Michael had purchased two quick picks that day.

Michael insisted that if he had purchased any for Abraham Shakespeare, then he would have had

four tickets in total. According to Michael, he tucked the tickets into his wallet, which he

kept in an overhead compartment inside his truck.

Michael said he realized his lottery tickets were missing the following day.

He assumed that he'd lost them until a supervisor informed him that Abraham won the jackpot.

Michael confronted Abraham and accused him of stealing the tickets while he'd been left alone in the truck.

Abraham allegedly admitted to swiping the tickets from Michael's wallet.

Michael said Abraham had offered him a million dollars to put the matter to rest,

but he'd decided to file a lawsuit against Abraham instead.

Abraham flatly denied these allegations, saying,

Michael Ford knows the truth. I know the truth. The Lord knows he doesn't deserve it.

It's like a dirty money. That money was stolen from him.

According to Abraham, after his win, Michael asked Abraham to look out for him by giving him a million

dollars so he could move into state and start a business. Abraham was willing to help,

but lottery officials hadn't wired him the money yet, so he told Michael to be patient.

He also offered a smaller amount of money.

He also offered a smaller amount of money, but he didn't have the money to pay for it.

So he told Michael to be patient. He also offered a smaller amount,

as he felt a million dollars was excessive. Michael confronted Abraham again two days later,

this time indicating his intention to sue. Abraham explained,

When Michael brought up the word court, I backed away from him.

I told him I don't owe him nothing. I told him if you feel like you have a case,

go on to court. By the time Michael came for Abraham's prize money, there was $12 million left.

Michael sought injunctive relief, which would immediately freeze Abraham's assets and prevent

him from spending any more of the winnings. A circuit court judge ruled in Michael's favor.

The matter went to court in October 2007, five months after Abraham's big win.

The dramatic proceedings became a public spectacle.

Michael Ford's attorney worked to undermine Abraham's character by repeatedly bringing

up his criminal past. At age 13, Abraham was caught stealing from a convenience store and

sent to a state-run juvenile reform school. He remained there until he was 18, then proceeded

to rack up a range of offenses that included trespassing, assault, and theft. As an adult,

he amassed seven felony and three misdemeanor convictions, resulting in two stints in prison.

Michael Ford's attorney asked the court, Does a leopard change its spots?

When witnesses are tested to Abraham's good character,

Michael's counsel accused Abraham of paying them off for their testimony.

In turn, Abraham's attorney accused the plaintiff of piling dirt on his client,

saying that bringing up his criminal record was an attempt to distract the jury from the

pertinent issues. They questioned why Abraham would steal the lottery tickets,

which were worthless at the time the alleged theft occurred.

Abraham had no way of knowing one would win the jackpot.

Abraham also had an extensive history of playing the lottery. To prove it,

he carried a garbage bag into court stuffed with tickets he had purchased over the years.

Michael was revealed to be a liar. In sworn testimony as part of the pre-trial discovery

process, Michael said he'd lent Abraham money in the past to help put food on his table.

But during the trial, Michael denied ever helping Abraham at all.

After five days of testimony and a little over an hour's deliberation,

the jury unanimously agreed that Abraham Shakespeare did not steal the lottery tickets

from Michael Ford. Michael was denied any of Abraham's winnings.

Abraham's lawyer told the media,

this lawsuit was about greed. The plaintiff manufactured a story and a plan to try to

take advantage of my client. While Abraham felt Michael had scandalised his reputation,

he ultimately forgave him. He didn't harbour any anger, saying,

That guy used to be a real good friend of mine. If he only waited, I could have

given him $250,000 easy. Michael rejected the jury's findings and began a lengthy

appeals process. The final hearing was scheduled for Wednesday, May 27, 2009,

two and a half years after Abraham won the lottery.

Michael Ford's appeal was ultimately dismissed, but Abraham Shakespeare wasn't around to hear

the good news. No one had seen Abraham in the weeks leading up to the hearing,

and calls to his cell phone were going unanswered.

Words spread that he'd skipped town to avoid the spotlight and get some much needed rest.

Since his lottery win, Abraham had become a father for the second time. He'd separated from the

baby's mother shortly after the birth, and the pair had been embroiled in hostile court

proceedings ever since. There was gossip that the woman had intentionally become pregnant

just to access Abraham's money. This fuelled a belief that he'd fled to avoid paying child support.

He also had an unpaid bill with the law firm that fought his civil suit.

The rumor mill swung into overdrive. Some claimed Abraham was doing business or receiving medical

treatment overseas. Others accused him of being on the run from police. Those who knew Abraham

best denied these assertions. There were even rumors that he'd died of AIDS,

despite some alleged sightings of him around Lakeland.

Prior to winning the lottery, Abraham spent several days a week doing odd jobs at a barbershop

owned by his longtime friend, Greg Smith. Greg saw firsthand the overwhelmingly negative impact

that the win had on Abraham. His sunny disposition faded, and he often told Greg,

I wish I could go back to my old self.

Greg had been struggling to stay on top of his mortgage repayments, but he'd kept this from

Abraham as he didn't want to be seen as another moocher. One day, Abraham spotted banking documents

at Greg's barbershop. Realising his friend was in trouble, he paid off Greg's $63,000 mortgage.

Greg agreed to give Abraham $500 a month until the debt was repaid.

When Abraham abruptly left Lakeland and stopped answering his phone, Greg sent him a text message

that read, call me, it's important. Abraham messaged back, bro, I'm on a cruise and I'll be back in

town soon. I just needed to get away because all these people are bothering me about money.

Greg told Abraham to call him immediately.

Abraham replied, I'll call you in the morning, I'm just trying to get myself together.

Greg was struck by the exchange. Abraham's limited education meant he struggled to read

and write. He preferred calling or speaking with people face to face over communicating through

text. Abraham's messages were also unusually formal. They didn't reflect his usual speech and

writing patterns. Greg's wife agreed that the messages were odd. She sent Abraham a text asking

him to come home. He replied, I'll be home soon and I'll call you when I get back.

Days passed but Abraham didn't call.

Abraham was a doting father who typically called his elder son twice a week. These calls also stopped

and were replaced by text messages. He sent one acquaintance upwards of 60 texts but still made

no calls. In his messages, Abraham assured everyone that he was fine and okay. During one

exchange, he was uncharacteristically belligerent, referring to himself as a grown-ass man who

would return to Lakeland when he was ready. Increasingly suspicious, one of Abraham's associates

texted a question that only he could answer. There was no response.

A few people tried to report Abraham missing but were dismissed because they weren't family.

Abraham's mother, Elizabeth, considered doing so as Abraham wasn't the type to go away for

long periods without getting in touch. But one of her nephews, Cedric Adam, said that Abraham

was calling him daily. He had also received a birthday card for Elizabeth from Abraham.

It contained $100 and a necklace along with a handwritten message that read,

I'll be home soon, followed by Abraham's signature. Elizabeth recognized her son's

handwriting, which temporarily quashed any niggling concerns.

By November, seven months had passed since Abraham left Lakeland.

Thanksgiving was one of his favorite holidays. When the day came and went without any word,

Abraham's prolonged silence became too loud to ignore.

Abraham Shakespeare was officially reported missing. Finding him wasn't going to be easy.

Abraham was accustomed to living a transient lifestyle. At the time he left Lakeland,

Abraham was dating a woman named Courtney Daniels. Courtney told police the last time she'd seen

Abraham was the first week of April. He'd dropped her at a bus station so she could visit a friend

interstate. That night, the couple spoke on the phone for hours, but after that, Courtney never

heard another word. She soon learned of a rumor that Abraham had left Florida with another woman.

When she returned to Abraham's house to pack up her things, all of his belongings were still there.

After winning the lottery, Abraham grew tired of all the paperwork and meetings related to his

finances. He'd sought help from a friend of 15 years, Judy Hagens, who assumed the unofficial

role of his assistant. Abraham eventually designated Judy as his power of attorney.

This meant she had control over all of his financial decisions and could handle his affairs

whenever he went away. Others viewed this decision as absurd. Judy had no business or legal

qualifications and was viewed by some as a party girl. Regardless, Abraham signed the papers in

early April of 2009, shortly before he disappeared. Judy told police she hadn't seen him since.

Abraham had been scheduled to appear in court in August for a child support enforcement action,

but never showed up. His attorney, Howard Stitzel, told the court that Abraham was out of the

country receiving medical treatment for an undisclosed illness. When questioned by police,

Howard said the last time he'd spoken to Abraham on the phone was in October,

almost six months since he'd last been seen in Florida. He was reluctant to divulge the

specifics due to attorney-client privilege, but was absolutely certain it was Abraham

he'd spoken to as he was familiar with his voice. Abraham hadn't sounded distressed and there had

been no follow-ups. Due to the conflicting rumors regarding his whereabouts, police weren't sure

what to make of Abraham Shakespeare's disappearance. They accepted the possibility that he was simply

lying low to avoid the struggles he'd faced since winning the lottery. In public appeals,

they indicated they'd leave Abraham be as long as he reached out to confirm he was okay.

Police also considered that Abraham might have met with foul play. At the peak of his

affluence, Abraham had drawn a lot of ire. Following his failed civil suit against Abraham,

Michael Ford moved to Georgia where he resumed work as a truck driver. He admitted to police

that he'd returned to Florida a couple of times, but maintained it was only for work.

Michael said he hadn't seen Abraham since their court battle and he had no idea where he might

have gone. An examination of Abraham's bank account revealed he'd made several withdrawals

in the months leading up to his disappearance, but none since. The account also revealed a harsh

reality. Within three years, Abraham had spent, given away, or loaned almost all of his $17 million.

Only $45,000 remained. While murder still couldn't be ruled out, it seemed highly unlikely that anyone

would kill Abraham for such a small amount. He also had no life insurance, meaning no one stood

to legally claim his remaining money upon his death. Detective David Wallace was part of a team

fronting the search for Abraham Shakespeare. One day, he received a phone call from an anonymous

mail who asked for him specifically. When Detective Wallace asked who he was speaking to,

the caller replied, It don't matter who this is. I'm down here in Miami and just want to let you

know I saw Abraham Shakespeare in a damn strip club. He reached in his pocket for something and

his ID fell out and I saw it was him. Detective Wallace asked when, but the caller abruptly hung up.

The call puzzled Detective Wallace. It wasn't traceable, so he couldn't verify it.

He was also aware that in high-profile cases like Abraham's, pranksters often stirred up mischief

for police. Maybe someone was looking to insert themselves into the investigation

or seeking the $5,000 reward for information. By Christmas, almost nine months had passed

since the last confirmed sighting of Abraham. Two days later, his mother Elizabeth received a

call of her own. She remained calm when she heard the familiar voice of her missing son come through

the line. Hey Ma, I just want you to know that I'm okay and I'm going to see you soon.

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Abraham told his mother not to worry and said that he loved her.

Elizabeth asked, where you at, baby? Abraham remarked that it was too noisy for him to hear her

clearly. Elizabeth raised her voice, again asking Abraham where he was and when he would be coming

home. The phone line then went dead. Detectives traced the call to Barbara Greg Smith, Abraham's

longtime friend and former employer. Greg was put under covert surveillance and detectives watched

as he drove to a parking lot near Lakeland Mall. A second vehicle arrived shortly after,

driven by a middle-aged white woman with bleached blonde hair. She got out of her car and handed

Greg some cash. He then drove off, unaware he was being tailed by an unmarked police car.

When Greg stopped at a red light, detectives surrounded his vehicle and ordered him out.

Greg appeared calm, saying, I'm more than happy to talk to you all.

Greg admitted to calling Abraham's mother and pretending to be her missing son.

He also confessed to calling Detective David Wallace to report a false sighting of Abraham

in Miami. Greg was apologetic. He said he'd been paid to make the calls by the woman he'd

met in the Lakeland Mall parking lot. Her name was Dee Dee Moore. Greg thought he was doing

Abraham a favor by making the calls, adding, I don't know anything about where Abraham is,

why he's gone, or when he's coming back. I've been trying to reach him myself.

Detectives also spoke with Abraham's cousin, Cedric Adam, who said he'd received a birthday

card and daily calls from Abraham. Cedric admitted he'd been lying. He claimed he'd been paid around

$5,000 to spread the word that Abraham had gone away of his own accord. Cedric desperately needed

money and only agreed because he thought it was harmless, just a way to help Abraham and debate

his aunt's worry. When asked who paid him to lie about Abraham, Cedric said, this woman named Dee

Dee Moore. Dee Dee Moore was a certified nurse's assistant who ran a nursing staffing agency

called American Medical Professionals. In 2008, she attended a small business conference in Florida

where she observed a panel discussion featuring a real estate agent. The agent spoke of having

once sold a house to a lottery winner named to Abraham Shakespeare. He had changed the way she

viewed wealth, specifically that money does not equal happiness. After hearing Abraham's story,

Dee Dee Moore was inspired to write about him for a magazine article. In October 2008,

she arranged to meet Abraham. By this point, his $17 million had been whittled down significantly.

He had a little over a million dollars left, along with just $3 million worth of assets.

Dee Dee quickly realized that his rags to riches story was in fact a riches to rags one.

She witnessed firsthand the endless pestering Abraham endured from those seeking what little

money he had left. He was downtrodden and distrustful. When Dee Dee pitched her article idea in which

she intended to highlight Abraham's generosity and kindness, he became noticeably upbeat.

Dee Dee filmed a candid interview with Abraham as he watched a live feed from the various security

cameras positioned around his home. Dee Dee asked if he ever got tired of people asking him for money.

Abraham replied, I've been tired. They don't take no for an answer. So I just let him keep on keeping on asking.

In time, Abraham confided in Dee Dee about his dire financial straits. He'd followed poor advice and

failed to invest his money wisely. Dee Dee felt sorry for him. She offered to protect Abraham from

being taken advantage of any further. Although she was shy and meek, she pursued those who had

borrowed money from Abraham and ensured they made repayments. She also organized for Judy

Hagans to have power of attorney over Abraham's remaining money. This meant anyone who wanted

funds would have to go through duty. Abraham had been moving his money from bank to bank on a whim.

Dee Dee advised him to secure his leftover money in a single Bank of America account under his own name.

Dee Dee, Abraham and Judy got together periodically to discuss Abraham's finances,

with Dee Dee keeping record of the meetings for the bank. She was dismayed to learn that

Abraham was using his money for what she had noted as criminal activity. He was removed as

an authorized signer of his account, leaving just Dee Dee and Judy with access.

They became a buffer between Abraham and any unwise financial decisions.

Dee Dee also helped manage all of Abraham's assets, including his property.

Dee Dee encouraged Abraham to start living his life. In their recorded interview,

she asked where he would like to go. He responded,

It don't matter to me, I'm not a picky person.

Dee Dee offered suggestions, California, a foreign country.

Seemingly irritated by Dee Dee's prying, Abraham motioned for her to turn off the camera.

Are you going to miss your home, Dee Dee asked. Abraham responded, Yep, but life goes on.

Dee Dee got the sense that Abraham was planning to take off at any moment.

Then one day, he told her he'd obtained a fake passport under the name Rodriguez.

Abraham began working to break his ties to Lakeland as quickly as possible.

He offered to sell Dee Dee his house for a little over $500,000. She didn't have that

much money, but the pair reached an agreement. Dee Dee could live in the house and make small

purchases for Abraham, such as flights or cruise tickets, as a gradual means of paying off the debt.

Abraham then asked for Dee Dee's help to make him disappear.

Having grown attached to Abraham and his plight, she agreed.

When Abraham left Lakeland, Dee Dee spread conflicting rumors about where he'd gone and why,

to prevent him from being traced. She also shared alleged sightings of Abraham so people knew he

was all right. He had left Dee Dee his cell phone, allowing her to send texts on his behalf to his

friends and family. Whenever concerns for Abraham grew, Dee Dee used money he had given her to pay

people to claim they'd heard from him. She paid Greg Smith $300 to call Detective David Wallace

and report a false sighting of Abraham in Miami. She gave Greg a further $350 to call Abraham's

mother. She'd even broken attorney-client privilege by staging a call to Abraham's attorney in October.

Abraham had told her, you handle all the business, I got to go.

When approached by detectives, Dee Dee became emotional as she divulged what she'd done.

She claimed not to know where Abraham was, but maintained that the two had met up and spoken

since he fell off the grid in April 2009. Dee Dee said she'd initially been under the impression

that she was simply keeping things in order until Abraham came home, but over time she suspected

he never intended to return. She felt she had misjudged him, saying, I've got all this trouble

on me when all I was trying to do is help the man. Dee Dee willingly assisted investigators with

their inquiries. Eventually she admitted there were several other reasons Abraham might have fled.

She disclosed that the real reason Abraham had her manage his money was to avoid paying child

support. He also had a drug problem and might have been lured into dealing in a desperate bid to

rebuild his wealth. Then Dee Dee mentioned an incriminating videotape. It allegedly showed

footage of Abraham, quote, having sex with a 14 year old girl. Whatever the case, Abraham's friends

and associates in Lakeland agreed on one thing. If anyone knew where Abraham was, it was Dee Dee more.

Dee Dee's admissions put her directly in the spotlight.

Reporters confronted her in public, police constantly requested interviews and her computer

files and business records were taken for examination. To quell the mounting suspicion

against her, Dee Dee did her own work to find Abraham. She met up with Greg Smith, the man

she'd previously paid to make fraudulent calls on Abraham's behalf. Dee Dee ventured to Greg

about the stress she was under and to Greg reassured her that he would help until Abraham reappeared.

Dee Dee's demeanour suddenly changed. She clawed at Greg's chest looking for a listening device.

Greg pulled away angrily asking, what the fuck you're doing?

Dee Dee composed herself and apologised. She was riddled with anxiety and paranoia and didn't

know who to trust. She blamed Abraham for leaving her to clean up his mess and Greg consoled her.

Dee Dee cried and told him, I see why Abraham says you're a good friend. I just want to thank you

for believing in me and being on my side. December 2009 came to a close with no sign of Abraham

Shakespeare. In late January 2010, Dee Dee Moore met with Greg Smith again.

The pair spoke about how the police were purposefully stirring shit up by intimidating

Abraham's support network. Phones had been tapped, homes were searched and property seized.

Dee Dee believed the police were trying to get them to change their story.

Greg encouraged her to remain strong, reminding her that they were in this together.

I've only been talking to you because I'm trying to find Abraham, Dee Dee said.

I've never been so scared in my life.

Tensions were growing in the Lakeland community. People were accusing Dee Dee of ripping off

Abraham and she feared violent reprisal. She informed Greg that Abraham was connected to

several gun and drug dealers and this made her particularly nervous.

Dee Dee had told the police who these men were, prompting the police to confront them with Dee

Dee's accusations. That was when she realized that the police didn't care if she was killed.

Dee Dee also told Greg that she'd been approached by Abraham's cousin, Cedric Adam,

whom she'd previously paid to lie about Abraham. Cedric told Dee Dee that he'd been in contact

with Abraham and said he wanted Cedric to have his home on Red Hawk Bend Drive.

Dee Dee was unsure what to do about this. If it was true, Cedric could establish a line of

communication between Abraham and the authorities. Yet, Cedric wasn't exactly credible.

Then there was Dee Dee's own distrust of the police. She had grown to suspect that they were

trying to frame her for Abraham's disappearance.

Dee Dee and Greg bought burner cell phones so they could communicate freely.

One night, they met at a comfort inn where Greg booked a room under a fake name.

Dee Dee was first to arrive. Anxious about leaving any trace of her presence,

she donned plastic gloves, a surgical mask, disposable shoe covers, and a hair net.

When Greg showed up, he put on the same protective outfit.

Dee Dee was fed up and had decided to take matters into her own hands.

She pulled out a laptop and printer. With Greg's help, she started typing a letter

addressed to Abraham Shakespeare's mother, Elizabeth. But the letter wasn't going to

be from Dee Dee. She was writing it as though it was from Abraham himself.

Convinced that Abraham wasn't coming back to help her,

Dee Dee was desperate to redirect the investigative spotlight.

Greg advised her, don't mention yourself too much, otherwise it will come off as suspicious.

The letter was several pages long and gave various reasons why Abraham wanted to leave home.

Dee Dee wrote, I like being missing, just not all over the news. I've been through a lot Mum,

you know it. I'm just tired.

She made up a story that someone had recognized Abraham and he'd had to pay a police officer

$20,000 to keep his secret. In reference to herself, Dee Dee wrote,

Don't worry about Dee, if she goes to jail she will be okay, the charges won't stick.

There are too many people that know I left. I gave her enough money. She knew what to expect.

She should have not gotten involved, so now she just has to deal with it.

Remembering that Abraham was illiterate and incapable of writing long-winded prose, Dee Dee

added, I still can't write a letter, a good friend is typing it for me. I will see you,

I promise. Just give me some time.

Greg Smith was impressed. The letter didn't sound like it had come from Dee Dee at all.

They printed it off and slid it into an envelope. The pair wiped the room down with towels.

Then they drove to Abraham's mother's home, where Greg placed the letter in her mailbox.

But any hopes that the letter would help Dee Dee were dashed when it failed to make the news?

Elizabeth didn't speak about it publicly, and the police seemed unaware of its existence.

Instead, investigators upped the reward for information to $10,000,

with the promise that any tipsters wouldn't have to testify in future court proceedings.

The county sheriff announced,

none of the circumstances and none of the investigation we've completed up to this point

leads us to believe Abraham Shakespeare is still alive.

They officially named Dee Dee more as a person of interest.

Dee Dee was distraught. Had Elizabeth kept the letter to herself? Or were the police just keeping

it on the down low? Dee Dee called Greg Smith for guidance, expressing her devastation that

police feared Abraham was dead and that she was being viewed as a suspect.

Fuck all that, Greg told her. They don't have a body.

They don't have a body. Dee Dee brushed his reassurances aside, saying,

Yeah, but that doesn't seem to matter to these assholes. They're just trying to pin

something on me and I haven't done anything to the man. I would never ever do anything to

hurt another human being. All I have ever done is try to help Abraham.

Hours later, Greg agreed to meet Dee Dee at a service station in Plant City, 10 miles west of

Lakeland. As soon as Greg pulled up, a visibly overjoyed Dee Dee rushed over to his car, yelling,

Abraham's back.

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Hours later

Dee Dee could barely contain her excitement. Someone had called her to report seeing Abraham

at a home near Walden Lake. Dee Dee had gone to the location herself and spotted a car with a figure

inside. She was certain it was Abraham. Greg was flawed. He and Dee Dee went to the location,

but the car was no longer there. Regardless, Dee Dee was relieved. Soon, other alleged

sightings of Abraham began to spread, but to Dee Dee's disappointment, none of them made the news.

Greg tried to reassure her that the media were probably just being cautious,

given the case was riddled with rumours. Deflated, Dee Dee told Greg,

The police don't care. They just want to make me the fall guy for Abraham not being around.

Greg replied, Well, you need your own fall guy. You need somebody who will take this case for you.

Take the rap. He suggested Dee Dee find someone who was about to serve a long prison sentence

and cut a deal with them. What deal you cut is between you and him, Greg continued.

I'm just saying there are people who will do this for you and get the heat off us.

Dee Dee was excited by Greg's proposition. She asked if he had anyone in mind.

Greg said he had a cousin named Mike Smith who was about to serve 25 years on drug charges.

Dee Dee tearfully embraced Greg, grateful that he was still supporting her. He was, in her eyes,

an exceptional person. Greg reiterated that he had been with Dee Dee since the beginning and would

remain with her for the whole way. The pair approached Mike Smith with their proposal.

In exchange for $50,000, Mike would tell police that Abraham owed him money for a cannabis deal.

Because Dee Dee had been overseeing Abraham's money, she would say that Abraham requested

the funds from her, but she refused. A confrontation eventually ensued between the two men,

and Abraham pulled out a gun, prompting Mike to shoot him in self-defense.

Mike Smith agreed to become Dee Dee and Greg's fall guy. The money would provide security for

his family, and given he was going to prison anyway, he felt he had nothing to lose.

While Dee Dee was relieved by what she saw as a foolproof plan, she was starting to worry that

maybe Abraham wasn't alright. Perhaps he had been killed after all, and those who knew the truth

were being threatened to stay quiet. Dee Dee's suspicions fell on a man she knew only as Ronald,

the worst of the gun and drug dealers Abraham associated with.

In the wake of Abraham's disappearance, Ronald had initially told Dee Dee that Abraham was okay,

but as she'd started to sense that something was amiss, Ronald became aggressive,

threatening to kill Dee Dee and her teenage son. Menacing notes began appearing at Dee Dee's

back door, which she was certain were from Ronald. Greg encouraged Dee Dee to confront Ronald,

even suggesting she bribed him to reveal key information. Dee Dee considered it,

but was more tempted by Mike Smith being willing to take the rap for Abraham's murder.

This would take the heat off Dee Dee entirely. The only problem was that Mike had made a specific

request. He needed a body. No one would take his story seriously without one,

and it would remove any doubt that Abraham was still alive.

Because they didn't have a body, Dee Dee hoped a murder weapon would suffice.

They could plant Mike's fingerprints on a gun and then have Mike direct people to the weapon.

She even had one they could use, a .38 caliber Smith and Wesson revolver.

Although it was registered in Dee Dee's name, Mike could say that he'd stolen it from her house,

or she could say that she'd sold it to Abraham. Better still, they could remove the weapon's

serial number to prevent it being traced altogether. Mike was reluctant to go through

with the plan without a body. He knew of someone who had attempted a similar con,

but the supposed murder victim had suddenly reappeared.

All the conspirators were charged with insurance fraud.

This rattled Dee Dee and she began to doubt the plan.

Confronting Ronald seemed safer. Perhaps she could offer him something to elicit a confession and

the location of Abraham's body. Greg ordered Dee Dee to call Ronald and find out everything they

needed to know. The next time Greg and Dee Dee met, she had an update. She'd gotten in contact

with Ronald and he'd told her everything. Abraham had indeed run afoul of the drug dealers and was

killed as a result. Ronald had intended to set Dee Dee up for the crime and admitted that he'd

buried Abraham's body on her property in Plant City. Dee Dee and Greg made a plan.

Under the cover of darkness, Greg and Mike would dig up Abraham's body. Dee Dee would stay at

Abraham's Lakeland home with her family, establishing her alibi. She suggested that

Abraham's body be taken out to the countryside and burnt. She gave Greg her revolver to prepare it

for Mike's confession before making a final revelation. Abraham was rumoured to have been

in possession of $67,000 when he was killed. She told Greg and Mike to search for it.

In the early afternoon of Monday, January 25, 2010, Greg arrived at Dee Dee's house on the

regional outskirts of Plant City. She supplied him with digging implements and cleaning products

before leading him to a 30 by 30 foot concrete slab in her backyard. She pinpointed a specific spot

saying, that's where you should dig, right under there, maybe six feet down.

Later that night, Dee Dee was in Lakeland as planned when she received a call from Greg.

Hey, thundered down the line. What the fuck are you doing?

He'd arrived at Dee Dee's to commence the dig, only to find a large police presence already there.

Greg and Mike backed away to a secluded spot and called Dee Dee, accusing her of setting them up.

I swear to you Greg, she told him, I don't know nothing about this.

Greg demanded to meet up. Dee Dee was reluctant as it would blow her alibi, but Greg was furious.

They needed a plan B and they needed it now.

Dee Dee agreed to meet Greg at the Lakeland Mall parking lot.

She told her family that she was going to help a friend who was having car trouble.

The pair sat in Greg's car, frantically discussing their options. Greg suspected

the police were tipped off and had a warrant to search Dee Dee's property, but Dee Dee

maintained that she hadn't told anyone about their scheme.

All of a sudden, two cars sped into the parking lot and pulled up beside Greg's vehicle.

Detectives emerged and took Greg and Dee Dee into custody.

Dee Dee immediately threw Greg under the bus, saying that he had killed Abraham.

The interviewing detectives eyed each other, before one remarked,

You know that Greg didn't kill Abraham Shakespeare.

Dee Dee began to cry, but insisted that Greg was guilty.

Then she was given news that left her speechless.

Greg Smith is working with us.

Greg Smith was first introduced to Dee Dee Moore by his good friend, Abraham Shakespeare.

Dee Dee, whose full name was Doris Donegan Moore, came across as timid and uneasy.

Her handshake was gentle and she struggled to maintain eye contact.

When Dee Dee began managing Abraham's money, Greg was skeptical.

She wasn't an accredited accountant or financial advisor.

She claimed to have written a financial self-help book called

Organize Me Now, but it hadn't been published.

Greg bit his tongue so as not to undermine Abraham's decision, but warned him to be careful.

He never saw his friend again.

With Abraham mysteriously out of the picture,

Dee Dee started chasing Greg to repay the $63,000 that Abraham had lent him for his mortgage.

Then, when Abraham was reported missing,

Dee Dee offered to eradicate the debt entirely, on one condition.

She needed Greg's help to mislead the police.

Dee Dee knew detectives would be on to her.

From a young age, she was acutely aware of the power and privilege of wealth,

and was ashamed of her own family's financial status.

In her teens, she made her parents drop her off away from her friends

so they wouldn't see their cheap old car.

She sought luxuries her parents couldn't afford, like expensive clothing, cars, and a jewellery.

At age 22, Dee Dee was involved in a head-on collision.

The two occupants in the other vehicle were killed, but Dee Dee made a full recovery.

Afterwards, Dee Dee's mother noticed an erratic shift in her daughter's behavior

that left her wondering if Dee Dee had an undetected brain injury.

Her job as a nursing assistant suited her seemingly kind and patient personality,

but it didn't pay well.

Still fixated on money, Dee Dee established a moderately successful side business

selling prepaid cell phones and calling plans.

Colleagues recalled Dee Dee's natural acumen for business,

but it was soon revealed that she had skimmed $60,000 off the payroll.

Dee Dee's money woes continued.

She was caught shoplifting and arrested for writing a bad check.

She failed to make her car repayments and was evicted for failing to pay rent.

By mid-2001, she owed upwards of $50,000.

Not long after this, Dee Dee was discovered in Waimama,

40 miles south from her home in Plant City.

She was dishevelled and distraught with her wrists bound with duct tape.

Dee Dee told police that three clean-cut,

tattooed Hispanic men had carjacked her at gunpoint.

They abducted and raped her, then thrown her in a ditch before taking off in her car.

A tip-off led to the discovery of Dee Dee's car in a garage 30 miles north in Pasco County

and to the complete unraveling of her story.

Dee Dee had paid an accomplice to help stage the attack so she could claim

insurance on her stolen car.

She was convicted of insurance fraud and falsely reporting a crime and given a year's probation.

Years later, in 2006, Dee Dee was accused of stealing $60,000 that was given to her to start

a new business. The case was closed due to a lack of evidence.

After this, Dee Dee faced two civil lawsuits for unpaid services.

Fronting her new venture, American Medical Professionals,

she attended the small business conference that ultimately led her to Abraham Shakespeare.

Within 90 days of the pair meeting, Dee Dee more virtually had complete control of Abraham's money.

Investigators discovered that the final withdrawals from Abraham's bank account,

as well as his assets, were transferred to the business account of American Medical Professionals.

Around this time, Dee Dee made large withdrawals from this account, purchasing jewelry and several

high-end cars, as well as paying for restaurant meals and travel.

While Dee Dee was seemingly helping Abraham reclaim money he'd loaned to others,

the repayments actually went straight to her.

Dee Dee claimed to have bought Abraham's mansion home from him,

but there was no documentation to prove it. When detectives confronted her with this

discrepancy and many others, Dee Dee altered her story with even more outlandish explanations.

Some were willing to believe that Dee Dee's dealings with Abraham were just

unscrupulous coincidences and that he was indeed in hiding.

Others were certain he had met with foul play,

but there wasn't sufficient evidence to support an arrest.

Everything pertaining to Dee Dee more had been searched. Aside from her efforts to claim

Abraham's last million dollars, not a single thing was found to indicate that she had physically

harmed him. It wasn't until detectives interviewed Greg Smith and learnt he was in

cahoots with Dee Dee that they formulated a plan.

We think Dee Dee more does know something, they told Greg,

and we need someone to help us get that information out of her.

Greg was then asked to become a confidential informant.

It wasn't a decision Greg made lightly, but he harboured his own suspicions about Dee Dee.

He spoke to Judy Hagans, the other person involved in overseeing Abraham's finances.

Judy recalled a time when Dee Dee called her in a panic.

Abraham was heading to the bank and Dee Dee needed Judy to stall him.

He can't go to the bank, Dee Dee told her.

Abraham once confided in Judy,

now you know that white woman got me money, she can do anything to me.

Greg had a gut feeling Abraham was dead. He told Detective Wallace,

I'm in, whatever I got to do, I'm all in.

During their initial meeting, Dee Dee launched herself at Greg,

suspecting he was wearing a wire. He was able to reassure her.

They met multiple times over the following weeks. All the while,

Greg covertly recorded their conversations.

Dee Dee spouted off unbelievable stories non-stop,

barely giving Greg a moment's silence. One minute she was sobbing in his arms,

the next she'd snap to a composed state and rattle on about a different subject.

She seemed to lose herself in her convoluted lies and made up a dangerous drug dealer named

Ronald to implicate in Abraham's disappearance. Later she talked about Ronald as if he were a

real person. Greg was disturbed. Still, he went along with whatever strange plot Dee Dee devised

to hinder the investigation, all the while hoping she'd reveal what really happened to Abraham.

When she wrote a bizarre, rambling letter to Abraham's mother as Abraham, Greg felt it was

completely unconvincing, but told her otherwise. After the pair dropped it off in the mailbox,

detectives swooped in and took it as evidence. Greg endured a lot in his role as an informant.

His local community saw him spending time with Dee Dee and rumors spread.

Many suspected the pair had conspired together to get rid of Abraham. It was far from the truth,

but Greg couldn't defend himself lest he ruin everything he was working for. He couldn't let

Dee Dee get away with it. When she started talking about Abraham being dead, the operation

kicked up a notch. An undercover police officer was brought in to play Mike Smith, Greg's

prison-bound cousin. Using Mike as a fall guy, Greg extracted more compelling evidence from

Dee Dee, specifically where they would find Abraham's body. The realisation that Abraham

had been murdered was heartbreaking for Greg, but he had succeeded in locating his friend.

After learning that Greg Smith was a police informant, Dee Dee Moore took a long, deep breath.

She then implicated Mike Smith. Learning that he was an undercover detective,

she burst into tears and began a long rant blaming drug dealer Ronald for shooting Abraham with her

gun. It was no use. Detectives already had audio recordings of Dee Dee fabricating the

character of Ronald to Greg Smith. She went on and on about Ronald before a detective cut her off,

saying, Dee Dee, Dee Dee, there's no Ronald. She tensed up before telling a new story about

a drug deal gone wrong. Dee Dee claimed someone held a gun to her head and she'd passed out from

fear. She came too, only to witness Abraham being fatally shot. The detectives asked who the shooter

was, but Dee Dee started, saying she couldn't remember. One detective remarked, you can't tell

us because it's you and you're scared. Dee Dee's ex-husband revealed that he'd

delivered a backhoe to her plant city home in April 2009. He used it to help Dee Dee dig a large hole

as she wanted to burn and bury some remodeling debris. She asked him to return hours later to

fill the hole with dirt. A cement contractor poured the slab in Dee Dee's backyard that same

month. She told him she wanted a solid slab to park her vehicles on.

Eventually, Dee Dee would admit that Abraham's body was buried under the concrete slab in her

backyard. Following two days of excavation work, Abraham Shakespeare's remains were uncovered

six feet below the slab, nine months after he'd disappeared. He'd sustained two 38 caliber gun

shots to the chest, but the bullets were too deteriorated to be compared to Dee Dee's revolver.

She continued to give other explanations for Abraham's murder, each more outlandish than the

last. She implicated everyone from Abraham's cousin Cedric Adam to his attorney Howard Stitzel.

At one point, Dee Dee claimed she and Abraham had fought over money and he'd gripped her throat.

As she started to lose consciousness, someone shot Abraham, but she didn't see who.

She conceded that it could have been her, but if it was, it was in self-defense.

Just when detectives thought they'd heard it all, Dee Dee said her 14-year-old son was responsible.

She then tried to convince her ailing, elderly father to confess to the murder.

In the eyes of detectives, it was clear that Dee Dee was a habitual and shameless liar.

They described her as a professional con artist, a devil in disguise.

Dee Dee Moore was charged with the first-degree murder of Abraham Shakespeare.

Dee Dee's trial commenced in November 2012, six years after Abraham Shakespeare won the lottery.

The prosecution posited that Dee Dee had fanned Abraham's fears of losing his remaining wealth

by exaggerating the amount he'd lose to paying child support. Up until that point, Abraham was a

good father. Then Dee Dee filled his head with lies about infidelity and the possibility that

his youngest child wasn't even his. Abraham took Dee Dee's word that she'd protect his money if

he granted her access to it. When he realized he was being scammed, a confrontation ensued.

Dee Dee shot Abraham with her revolver before burying his body in her backyard.

She then went about creating conflicting rumors and false sightings to hinder the search for Abraham.

There was no shortage of witnesses testifying against Dee Dee,

including the star witness, Greg Smith, whose covert recordings were played.

During court, Dee Dee often broke down in tears, bringing proceedings to a halt.

She kept winking, smiling and gesturing to the jury. On one occasion, she apparently went into

anaphylactic shock. The judge cautioned the defense attorneys to control their client.

She was so disruptive that the judge eventually cut off her microphone.

The defense highlighted that the case relied on circumstantial evidence.

While they admitted Dee Dee was devious, they argued there was no proof she'd committed murder.

Her refusal to provide a clear explanation of Abraham's murder was indicative that her life

was in danger and she feared speaking the truth. The defense called no witnesses,

instead relying on painting the prosecution witnesses as untruthful or unreliable.

The jury deliberated for three hours before finding Dee Dee more guilty of the first-degree

murder of Abraham Shakespeare. The presiding judge described Dee Dee as cold, calculated and cruel,

saying she was, quote, probably the most manipulative person that this court has seen.

Abraham Shakespeare was your prey and your victim. Money was the root of the evil that you brought

to Abraham. Abraham's mother Elizabeth was a religious person and fundamentally against

the death penalty, so the prosecution didn't push for it. Instead, Dee Dee Moore was sentenced

to life in prison without parole. Elizabeth expressed gratitude to the detectives that

led the investigation into her son's disappearance, saying,

without their dedication and persistence, we might never have found out what happened to Abraham.

During Abraham's memorial service, the large crowd of mourners gave the detectives a standing ovation.

Appearing in emotional media interviews from prison, Dee Dee Moore called

anyone who believed she was guilty an idiot. She blamed her verdict on her legal team's

refusal to let her testify in her own defense. With each new interview came a different version

of events pertaining to Abraham's murder. Then, in 2019, Dee Dee Moore appealed her conviction.

She apologized for her actions, this time claiming Greg Smith killed Abraham after finding out that

he was having an affair with Greg's wife. Her appeal was rejected.

An investigator involved with the case described these claims as typical of Dee Dee, saying,

she'll go down in her grave trying to blame this on somebody else.

People have asked me if I think she will ever come clean, and I say, absolutely not.

Dee Dee will die in prison, still claiming her innocence.

Dee Dee maintains her innocence to this day, yet she also accepts that her ever-changing

version of events is confusing, conclusory, and vague.

Lottery winners are often the target of harassment,

solicitations, scams, extortions, burglaries, kidnappings, and homicides.

Therefore, winners are advised to keep quiet, hire an attorney, and remain anonymous.

If an individual is legally required to collect their winnings in person,

it's common for them to wear a disguise to avoid the publicity.

When Abraham Shakespeare won the lottery,

regulations in his home state required all winners publicly reveal their name and city of residence.

In May 2022, Florida introduced a new law creating a public records exemption for the

names of people who win lottery prizes of $250,000 or more.

The exemption lasts 90 days from the moment the prize is claimed.

This is deemed sufficient time for winners to plan responsibly,

obtain financial advice, put their funds into investments, or leave their old lives behind.

One of the bill's sponsors said,

At some point in our lives, we all dream of winning the lottery.

Unfortunately for some, that dream becomes a nightmare.

In the aftermath of Abraham Shakespeare's murder, only a couple of $100,000 of his $17,000,000

lottery win were recovered. That money was placed in a trust for his sons.

At Abraham's mansion on Red Hawk Bend Drive, two welcome mats greeted guests at the front door.

One featured the message, bless this home. The other read, go away.

Jim Valenti was Abraham's appellate attorney during his civil suit in 2007.

At the time, Jim said, Abraham Shakespeare was a man who was very weary by the time he got to me.

I wonder if he wouldn't say he would like to go back to the day before he won that money.

you

Machine-generated transcript that may contain inaccuracies.