The Dumbest Lottery Winners Ever!

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The Dumbest Lottery Winners Ever!
Pablito's Way

Pablito's Way
Published on 03-03-2017

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Wonder who the dumbest lottery winners are? Learn all about the most fortunate people in the world and how they squandered away the millions of dollars they won!

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6- Abraham Shakespeare

The fact that someone with the last name Shakespeare would live a modern day tragedy, is perhaps, one of the best ironies imaginable, however unfortunate. Unlike the more famous Shakespeare, Abraham was toiling as a truck driver’s assistant. But when he won a THIRTY MILLION DOLLAR Florida jackpot in 2006, his life actually got even worse.

Rather than doing the math and deep diving into discounted cash flows, Shakespeare decided he was smart and could beat the guaranteed rate presented to him and instead opted for a lump sum of $16.9 million, significantly less than the $30 million annuity he was entitled to. Never mind the fact that he’s a truck driver and if he was actually good at finance he’d be in the industry. ANYWAYS, after buying a Rolex and making major mistake #1 with $1 million home, Shakespeare didn’t seem to go on any drug binges, or spending sprees. But like many before him, he had tons of people coming around asking for money.

In particular, he started a business with a woman named Dee Dee Morgan called Abraham Shakespeare LLC, with the goal of writing his life story...or something vague like that. Just a tip guys, you have to have accomplished something in life to sell an interesting story. Not just win the lottery.

What ended up happening was that Moore took full control of the firm’s money, withdrawing $1 million from the bank, buying cars and may have even managed to buy Shakespeare’s home for something like $665,000...which is less than he paid for it. A later investigation suggested she didn’t even pay anything for the house...which is way more of a ripoff! Oh yeah, tip #2. Never ever ever ever let someone else control your actual money! I don’t care if it’s your wife or husband. Unsecured liabilities, such as a company credit card with a fixed limit? Sure. But not your actual cash money.

By April of 2009 he went missing, with his friends and family unable to find any trace of him. Investigators were soon able to locate him at one of Moore’s homes...sadly he was bread and buried under a concrete slab. Moore was arrested and charged with the killing, though she offered up a few different defenses. It was drug dealers...no wait she killed him in self defense. She even went so far as to blame her 14-year old son. Investigators didn’t buy any of that, and she was charged with the crime. She’s currently serving a life sentence.

His story was featured on E!’s “The Curse of the Lottery” as well as an episode of American Greed. In the end, Abraham Shakespeare will be a tragedy that will hopefully serve as a cautionary tale for those who happen upon a great fortune in the future.

5 - Vivian Nicholson

In 1961, a British woman named Vivian Nicholson was given the opportunity of a lifetime. Her husband Keith managed to win more than 3.5 million pounds, a pretty big amount back then factoring in inflation. Her husband won the money off football pools….pretty much another popular form of gambling. She told the press that her plans were to “spend spend spend.” And she wasn’t kidding.

For the next few years she bought all kinds of stuff. Expensive cars, fur coats, lavish vacations, a huge ranch style home and a spectacular lifestyle that quickly caused their fortune to dwindle. When Keith flied in car crash in 1965 she was left with an enormous tax bill. On the top of that, the banks determined that what remained of Keith’s winnings belonged to his estate. Not Viv! She ended up bankrupt.


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