Everyone dreams of winning the lottery. However, suddenly coming into such a giant sum of money doesn’t necessarily mean smooth sailing. When greedy friends and family members come out of the woodwork, there is no telling how far they will go to get a piece of the money. Just ask Abraham Shakespeare, a Florida man who went from the luckiest guy alive to the star of a sinister mystery.

In 2006, Abraham Shakespeare won the $30 million lottery jackpot. After taxes, Shakespeare ended up with $17 million. Abraham went from rags to riches in an instant, and that’s where the trouble started.


As soon as Abraham won the enormous jackpot, so-called “friends” began looking for a piece of the pie. A friend who accompanied Shakespeare to the store to buy the lottery ticket was asking for $1 million. He would later claim that Shakespeare stole the ticket from his wallet.

The story was clearly made up, but it was still taken to court. Fortunately, Shakespeare won the case. However, he no longer felt safe in the neighborhood he grew up in so he moved to a gated community.

Lakeland Ledger

Soon people found out where he was living and continued to harass him for the money. Shakespeare was now alone, far away from home, and infuriated by the constant pressure from friends and family.

One of the more nefarious characters that appeared in Abrahams’s life around this time was Dee-Dee Moore. She was an old flame who sold Abraham on the idea that she wanted to become his financial manager.

Together, Abraham and Dee-Dee setup Abraham Shakespeare LLC, with Moore taking complete control of all of Abrahams’s finances. Up to this point, Shakespeare was incredibly careful with his money. His only substantial purchases were the million-dollar home he escaped to, a Rolex, and a new car.

Florida Department of Corrections

Dee-Dee saw an opportunity in Abraham. He wasn’t paying attention to his money, so he wouldn’t notice if she treated herself to $1 million worth of new cars and a luxurious vacation.


For a man who just won the chance of a lifetime, Abraham was strangely quiet, and the police finally figured out why: He had disappeared. Naturally, the first suspect was Dee-Dee Moore. She listed several places he could be, claiming she even helped him get away from the consistent harassment.


With no sign of Abraham, Moore began to sink into a financial hole. She had no money to pay off the cars and other items she bought. She was now in debt and in trouble. Moore even went so far as to fake a rape and kidnapping to claim she was extorted.  


Suddenly, there was a tonal shift, and people became wary of Shakespeare’s whereabouts. Family and friends that were previously pressuring Shakespeare for money were shocked and expressed genuine concern about Abraham’s condition.

Lakeland Ledger

Despite his sophisticated name, Abraham Shakespeare was illiterate. This was important, because out of nowhere, he began having fully coherent text conversations with his close friends and family. People became doubtful that they were speaking with the real Abraham. They were right, of course.

It was Dee-Dee they were talking to. Often times when she was asked potentially incriminating questions through text, she would leave them on read. She was now ducking away from her troubles and pretending to be Abraham Shakespeare.

Instinctively, Shakespeare’s family grew more concerned as time passed by without a word from the real Abraham. They eventually filed a police inquiry and directed authorities towards Moore’s home.

Lakeland Ledger

What the police found when they entered Moore’s house was disturbing. Buried 9 feet deep in her own back yard was Shakespeare’s body.

ABC News

Initially, Moore’s story was always changing and shifting blame. She claimed it was drug dealers or an estranged son. However, nothing she said would get her out of this one.

Fox 13

Police continued questioning Dee-Dee until she finally confessed. She stated that she had killed Abraham in self-defense, and alleged that Abraham was abusive. But with her track record, the cops were hardly convinced.

Lakeland Ledger

The authorities searched Moore’s home and unsurprisingly they discovered all of Shakespeare’s money, in cash. Dee-Dee had withdrawn all of the funds from the LLC and had been using them indiscriminately.

Lakeland Ledger

Moore was also caught attempting to pay off numerous individuals to take the fall for the crime. She was allegedly offering up to $200,000 for someone to speak to the authorities and say that they, in fact, murdered Shakespeare.


Dee-Dee was not outsmarting anyone. Her façade was oblivious, and the police had her pinned down. She was arrested and a bail of $1 million was set. Predictably, Moore had blown through the money and could not afford bail.

Dee-Dee Moore was found guilty of first-degree murder in 2012, and she was sentenced to life in prison. Let the story of Abraham Shakespeare serve as a cautionary tale if you ever become an instant millionaire. Shakespeare was far from the only lotto winner to regret his luck.

1. Ibi Roncailoli: She won $5 million in 1991, choosing to give $2 million to a secret child she had with another man, unbeknownst to her husband. When he found out, he poisoned her.

2. Evelyn Adams: As possibly the luckiest person ever, Adams won the New Jersey Lottery twice. Once in 1985 and then again in 1986. Her total winnings of $5.4 million were totally depleted within a few years, eaten up by gambling in Atlantic City.

3. Americo Lopes: He won the lottery after he and his coworkers went in on tickets together. He then lied and quit his job so he could keep all the money! Once they found out, they took him to court, and he had to pay up.

4. Jack Whittaker: He was already a millionaire when he won $314.9 million. He spent wildly at casinos and strip clubs, spoiling his granddaughter, too, who got into drugs. She died in an apparent homicide not long after. He stated that life was “easier before.”


5. Lou Eisenberg: After winning $5 million in 1981, he bought a condo in Florida and tons of vacations. His last check was cashed in 2001, and he now lives in a mobile home on social security. At age 81 he says he “lived for the day.”

6. Lisa Arcand: Compared to other winnings, $1 million dollars isn’t all that much. No one told Arcand this, as she bought a house and went on vacation before opening a restaurant. After her restaurant failed, she was broke saying, “it’s been very depressing.”

Katie McMahon

7. Willie Hurt: Based on any metric, it would seem that winning the lottery ruined his life. Only three years after he won $3 million form the Michigan Lottery, he was broke, divorced, and charged with attempted murder.

8. Suzanne Mullins: Many winners have fallen victim to companies that advance lottery winners their cash so they don’t have to wait out the payments. Mullins is one of those. After winning $4.3 million, she ended up owing over $100,000 to one of those lenders.

Suzanne Mullins Twitter

9. Michael Carroll: This Brit won the a $14 million prize at the age of 19 is now earning $300 a week at a factory job. After ten years, he had spent up his money. Mostly on drugs, reportedly snorting cocaine through a solid gold pen.

10. Urooj Khan: As a hardworking small business owner, Khan was excited when he won $1 million in 2012 and planned to expand his laundry business. Tragically, he was murdered by cyanide poisoning the day his check was mailed. His murder is still unsolved.

11. Callie Rogers: At just 16, Rogers was the youngest ever lottery winner in the U.K. She quickly squandered the $2 million prize on cosmetic surgery and partying, leaving her broke. She attempted suicide, and now says teens shouldn’t be eligible.

12. David Lee Edwards: After taxes, Edwards walked away with $27 million in his pocket. A year later, he had less than half left. He bought medieval weapons, jets and homes. His wife was arrested for stabbing her secret boyfriend, and Edwards died alone and penniless.

13. Billy Bob Harrell: Harrell was a Pentecostal preacher working at Home Depot. After winning $31 million, he spent it mostly on other people to the discontent of his wife. Two years later, she filed for divorce as he went penniless. He tragically took his own life.

14. Gerald Muswagon: In 1998 he won the $10 million jackpot in Canada. He spent the money on all the accouterments to a lavish lifestyle and picked up a bad drug habit. His life fell apart, and he sadly committed suicide in 2005.

15. Alex Toth: Like many people who come into tons of money, tax fraud is a common issue for lotto winners. After winning $13 million, Toth filed false returns and ended up broke and alone before his death ten years after winning.

New York Times

16. Marva Wilson: When you win the lottery, you have to know who you can trust. Sadly, Wilson was taken advantage of by someone she thought was a friend. The woman spent almost every penny of Wilson’s $2 million winnings.

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17. Janite Lee: When she won $18 million in 1993, she knew she wanted to make a difference. She donated her entire fortune to charity, even having a library built at Washington University. She also donated heavily to the Democratic Party.

18. Luke Pittard: This Welsh native won a $1.9 million jack pot while he was working at McDonald’s. He went on a spending spree of epic proportions, which had him right back at McDonald’s less than two years later.

19. Denise Rossi: When she won $1.3 million in the California Lottery, she kept it a secret. Then, she demanded a divorce from her husband. They went on with the proceedings. Two years later, he found out the truth and sued her for every penny she withheld.

20. Scream Masked Man: Based on all the information we’ve gathered about lottery winners, it comes as no surprise that this recent winner has chosen to hide his identity from the public. Possibly, this will save him from an unsavory fate.

21. John and Lisa Robinson: This couple from Tennessee won a massive jackpot of $1.5 billion! You’d think that kind of money would destroy them, but the couple has remained humble, choosing to retire early with their fortune and live quietly out of the spotlight.

22. Merle and Patricia Butler: When the Butlers won $218 million, they could’ve gone hog wild! Instead, the couple’s first call after winning their millions was to hire a financial advisor. Talk about smart!

23. Steve Tran: This Californian immigrant was working at a local deli when he won $648 million! As soon as he realized it wasn’t a joke, he called his boss and handed in his notice. Now, he still works at a deli… but this time, it’s one he owns!

24. Gloria MacKenzie: This grandmother was 84 years old when she won a $590 million jackpot! She wouldn’t have won at all if the woman in line ahead of her hadn’t allowed her to go first because MacKenzie seemed ill. Talk about lucky.

25. Cindy and Mark Hill: When this couple hit the jackpot, they were over the moon. They won $293.8 million, and as soon as their six-year-old heard about it, she knew the time was finally right: she asked for—and received—a pony.

26. Superstorm Sandy winners: After Superstorm Sandy destroyed their homes, these 16 friends banded together to buy a lottery ticket. They wound up winning more than $86 million to divide between them.

27. Abraham Shakespeare: This man was working a nine-to-five when he won $30 million and his life changed forever. Unfortunately, it wasn’t for the better. The money attracted the likes of Dee Dee Moore, who would seduce—and then murder—him.

28. Louise White: In 2012, White won more than $336 million after taking a quick trip to the grocery store. To make matters even more interesting, this was the first time the woman had ever purchased a ticket in her life!

The reason she went to the grocery store in the first place: to buy a container of rainbow sherbet. Rather than spends her millions, however, White put them into a fund for her family appropriately dubbed “the Rainbow Sherbet Fund.”

29. William Post: Post won $16 million when he hit it big, but it didn’t bring him happiness. Not long after winning, his brother tried to have him murdered. Later, his ex-wife sued him for half his earnings. He died $1 million in debt.

30. John and Linda Kutey: When the Kuteys won a jackpot of $319 million, they didn’t mind splitting the winnings with their friends and family. In fact, they did something pretty exceptional with their windfall…

The Kuteys actually donated a portion of their winnings to fund the opening of a local water park for the neighborhood children! What a selfless way to give back to the community.