The Dumbest Lottery Winners Ever!

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!

Subscribe to Pablito’s Way!

New videos Monday, Tuesday, and Friday!

New to Pablito's Way? Start here!

Watch some of my favorite vids below…..

Most Insane Mayweather Moments!

WEIRDEST Things Ever Found in Animals!

9 of the WORST diseases EVER!

Assassinations That CHANGED the World!

The Hottest Female Athletes!

11 Most Ridiculous Purchases by Floyd "Money" Mayweather!

Here are the dumbest lottery winners in history!

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 dead 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.


  • bornracer 230

    Abraham was an actual really nice guy. Tried to help people. Wasn’t stupid. Just unlucky.

  • Mr. Maldonado

    Being broke is a protection from ourselves 😂

  • Gear5 ZYF

    no surgery or medicine can make u smart, so money can’t buy u smart.
    stupid + money = tragedy, always

  • MyTeamsBettah

    You shouldn’t be claiming others are unintelligent when you can’t point out West Virginia on a map. You highlighted Virginia, not West Virginia.

    • jeff furrow

      MyTeamsBettah I about fell out of my chair when I saw that. Lol. Also when they showed the picture of ‘Jack Whitaker’s House’ burning…that was a row of town houses that was set on fire in Hinton by an arsonist…Many families lived there…But Jack Whitaker did not lol. Good video, to talk about people being stupid lol

    • Furry Wolfy

      Intelligence has NOTHING to do with knowledge… you’re just a moron lol

    • Furry Wolfy

      Intelligence is something that you’ve got from the start and knowledge is about things that you’ve learned about since then… considering the fact that not everybody needs to know about politics and so on to live their life , is enough to even let someone like u see that this are two different things…

    • Jessica Arnold

      Furry Wolfy hh

    • Bubba Kush

      MyTeamsBettah thank you

  • Shadowbane Gaming

    That wasn’t West Virginia highlighted in the #1 clip… It’s funny that you call these people stupid, but you don’t know basic geography

    • Fondell Muffs

      Lucas Cruz why are you on a tirade against anyone with WV pride? you are a very small person, probably in more ways than one…

    • Shadowbane Gaming

      Lucas Cruz Hey smart guy, I don’t live in WV. Or in any surrounding states. It’s ok man, we understand, you don’t know basic geography

    • Shadowbane Gaming

      Daniel Martinez That’s what I would say too, if I didn’t know where it was on the map…

  • Thomas VanMeter

    shut up, annuity is for morons, if you invest the lump sum, you quicky outgain the annuity with conpund annual return of 7% in the stock market; u do the math!

  • General Zod

    mr. carroll is a classic example of stupid. buying expensive customised cars and gaudy, rapper jewelry. those things will eat up tons of cash and have terrible resale value.
    throw in a gambling habit and it was inevitable he’d be broke soon. i mean if you’re already rich, why gamble?
    some folks are destined to be poor no matter how much money they got.

    • Jeff Vader

      Charlie miles Manson sorry last I heard he was collecting & emptying the bins for freebridge I’ll beleave what I have heard as I live in Kings Lynn the same town as this bellend as a pose to believe something in a youtube vid that in all likelihood is wrong

    • Charlie miles Manson

      Jeff Vader he now live in Aberdeenshire n works in a biscuit factory.he was all over the papers up here just last year

    • Catháin Ó Danachair

      cash rich, sense poor

  • Supes Me

    Didn’t make it 2 seconds in. Shakespeare was Murdered. Yeah that makes him real stupid. Screw your video. Thumbs down

  • dtip4life 8472

    If I won $10,000,000 I buy a ton of land,Have a moderate size but a high end off the grid home and live my life staying away from the mass of idiots that this world is fill of.

    • largol33t1

      +dtip4life, it also sounds very tempting to me. I would get a tiny shack and an AWD motorhome and try living off the grid. The money would be kept in a bank of course.

    • Jerome Truitt

      +BosoxnationI972 My uncle is worth 25 million he doesn’t play the stock market. Half my family is independently wealthy and none of them play the stock market. It’s land and real estate investments mostly.

    • Deborah Moore

      1800s sightings of big gfish in the sky

    • Y K

      dtip4life 8472 yes sure u will everyone says the same thing until they see the money. yes u will still shop at Walmart blah blah god

    • Y K

      Rick Charles I think you will find it is ‘proof read your writings’. oh the irony

  • Isela Guerrero

    #2 if he was hooked on coke why is he so fat? lol

  • VideoFanatic13

    Who names their kid Billy Bob?

  • Darrin Smith

    That was Virginia not West Virginia you fucking idiot

  • Hollow Point

    Of I won a significant amount of money I’d pay all my debt off a disappear. My wife and I have talked it over a hundred times. No one in our family would know where we were unless we wanted them to know.

    • chinafakeeggs

      Wow. You must have a crappy family. If I won the lottery, I would buy a private island and bring my whole family to come live on it with me.

    • Hollow Point

      +chinafakeeggs My family as it were only thinks about themselves. So if I win the lottery I’ll be thinking about me and my wife and boys.

    • chinafakeeggs

      That’s sad. Either your family is very dysfunctional, or you are really bitter. Everyone I know is struggling just to survive. My family does’t do much for me but I still love them anyway.

    • Hollow Point

      +chinafakeeggs You would have to know our history. Very selfish people. I don’t even have friends because I distrust people so much.

    • chinafakeeggs

      Well how about you go to a therapist and work through all that? A counselor can see things more clearly. A bad family can screw up your life, but you don’t have to let it.

  • DatGrA2b

    I don’t agree with Abraham Shakespeare if you know his story you would know he wasn’t the brightest person in the world and was taken advantage of because of his lack of education

    • DatGrA2b

      ROTAXD my god do you not no the definition of the word dumb??? he wasnt dumb he lacked an education he was more ignorant than dumb

    • ROTAXD

      Tragedy Strikes yes, I understand it would be nice if people would use some tact when describing an individuals disability or a not so “flattering” quality…I agree with that. But the fact that something comes across as rude does not make said decription wrong.

    • DatGrA2b

      ROTAXD again the word dumb does not describe his lack of intelligence or learn disabilities

    • ROTAXD

      DatGrA2b if you’re speaking of the dictionary definition of dumb, you’re right.

    • yusuf Abdul- Alim

      DatGrA2b he had a good heart he was blinded by his own rose colored glasses

  • Mike Lugo

    hell. whenever I get my lousy 1200 at tax return I get people around me asking for help . just say no and learn to protect yourself from people who play you for your money

    • Obijuan_the_Insane !

      Mike Lugo, and that’s how you end up in hell.. you have missed the whole purpose of life lol but don’t worry most people will agree with you 🙂 bah bah.. sheeps

    • Mike Lugo

      yeah but I enjoy my lousy 1200 tax return

  • Ryan Koehler

    You always take the lump sum payout. Always. You can’t pass lottery annuity payments on if you pass away either.

    • Gaming Made Simple

      Ryan Koehler I’m not sure but I believe in the event of winning a large sum like that and choose the weekly payments instead of a lump sum you can pick one person to continue receiving your money in the event of you dieing…. I can’t remember for sure but I believe it’s a 50 year payout… but if you choose some1 to take over payments after your death it does kinda make you a target for them so they can collect for themselves

    • jesterd14

      Before that, SIGN THE TICKET, then rent a post office box, call the phone company or your cell carrier and tell them you are getting threatening calls and want a new number. Go to the DMV, change the address on your license and registration. Close every email account, get off Facebook, Linkedin and every other social media platform. Go talk to a regular bank, believe it or not, there are people there that really can help you keep most of your money. Big banks have all kinds of planners that work for them. And they will bend over backward to help you. Hire a CFP and call a lawyer write a will. Then go cash the ticket in.

      Remember you only pay for a house once, but you’ll be paying property taxes and insurance on it forever.

      The annuity can be transferred just like any other asset can be.

    • maximus10463

      Jose Guzman anyone can count money, you’re a moron

  • thechosendude

    Poor people are poor because they can’t manage money. God’s honest truth. If you hangout with wealthy people, they are surprisingly stingy with money. Remember Obama’s federal stimulus when every American got a couple grand? Every big screen TV was sold out at Walmart and lottery sales were at record numbers…