The Dumbest Lottery Winners Ever!

The Dumbest Lottery Winners Ever!

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
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
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
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?
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.
After the loss of her husband, Viv allegedly
became depressed and started to drink a lot
of booze, though she later became sober.
She would go on to marry three more times,
work a short stint in a strip club, become
a Jehovah’s witness, and write an Autobiography
entitled Spend Spend Spend, which was later
adapted into a musical.
After seeing it, she gave it a rather neutral
review, stating the musical score and actors
were great, but that it didn’t reflect her
life all that well.
When she passed away in 2015, there were many
things one could say about her 79 years on
That she had a boring life wasn’t one of
Hey, you know what, I bet there was never
a dull moment with her, no matter how bad
her life decision were.
4 – Willie Hurt
There’s a number of ways to blow through
a massive fortune.
One of the most popular being, quite literally
“blowing” through it…if you catch my
In 1989, the family man from Lansing, Michigan
won $3.1 million from the lottery.
The next two years however, proved be a nightmare
for Hurt and those close to him.
Before he could even collect all of his winnings,
he was filing for divorce, separated from
his kids, and spending all of his money on
crack cocaine.
By 1991 he was charged for murder when he
allegedly shot his girlfriend in the head
during a 48-hour drug binge, which is exactly
what you’re not supposed to do to someone,
regardless of how much money you have.
Money doesn’t change people, which is something
I’ll agree with, but it certainly enables
them to scale up their terrible life decisions!
3 – Billy Bob Harrell Jr.
It took Texas native Billie Bob Harrell Jr.
less than two years to undo the good fortune
that winning 31 million dollars from the Texas
jackpot bestowed upon him.
In his case, he was just way too damn nice.
After taking his family on vacation, he quit
his job, gave money to his church, bought
cars and homes for his friends and family,
and gave away lots of money to charities.
For example, he once donated close to 500
turkeys for poor families.
However big his heart was, his ability to
manage his wealth wasn’t all that great.
Notice a theme here?
Here’s a tip: if you ever win the lottery,
and have never handled large sums of money
before, hire a real, LICENSED professional
for financial advice!
Don’t let that person be some quote, family
Anyways, after good ol’ Billy Bob brokered
a deal with a company who paid him a lump
sum in exchange for his annual payouts from
the lottery, he was left with far less than
he actually won.
After a divorce left him basically broke,
he tragically committed suicide in 1999.
According to TIME magazine, he once told a
financial adviser that winning the lottery
was the worst thing that ever happened to
What’s the lesson here?
It’s better to have a recurring cash flow,
than a lump sum.
Never forget that!
2 – Michael Carroll
In 2002, when 19-year old Michael Carroll
won the U.K National Lottery, he garnered
something of a celebrity status.
Carroll won close to 10 million pounds, or
just over 14 million US dollars.
His antics garnered him nicknames such as
the “lotto lout” or the “King of Chavs”
which he actually had engraved into a black
After a troubled youth, Carroll found work
as a garbage man and was just collecting trash
for a living.
When he won his massive fortune, Carroll didn’t
even have a bank account, so obviously he
had no clue about handling any sort of finance
Carroll claimed he planned to spend his money
frugally and save much of his money.
Ummm……are we supposed to laugh now or
Spoiler alert, obviously that didn’t happen
or else he wouldn’t be on this list, now
would he?
Instead Carroll became renowned for his partying
and gambling habits.
Now it’s worth noting that he already had
a petty criminal record when he won and was
wearing a nice little fashion accessory known
as an ankle monitor when he arrived to collect
his winnings.
I’m just trying to give you a point of reference
here on the type of dude we’re talking about
Carroll went and bought a mansion, one he
named “The Grange,” where he threw legendary
parties, complete with booze, drugs and prostitutes
Oh yeah, he would also hold amatuer demolition
derbies in his backyard.
Yeah, what the f*ck ran through my mind as
Believe it or not, throwing the types of parties
that would shock even The Wolf of Wall Street
or Jay Gatsby tends to attract some pretty
nefarious characters.
By 2012 he had spent all of his money, was
broke as hell, and camping out in the woods!
If there’s some sort of a silver lining
to somehow blowing through a $14 million fortune,
it’s that according to the Huffington Post,
he was able to kick his drug habit after losing
all of his money.
For example, he once claimed that when he
was rich, he’d wake up and do a line of
coke and wash it down with some beer…the
breakfast of champions.
The last we hear, he was working at a cookie
factory making 300 bucks a week.
He told the BBC that he appreciates those
wages much more than the fortune he fell a**
backwards in.
To be honest, I don’t think he’s being
real and I think he’s just saying that so
people don’t call him dumb, so I call bullsh*t.
But in case he WAS sincere, this dude lost
all his money, but gained some perspective…that
counts for something…..I guess…………psyche!!
Last time I checked, perspective doesn’t
pay any bills!!
Stay savage my friends.
1 – Andrew Jackson Whittaker Jr.
Many of the stories we’ve shared with you
here are surprising to say the very least,
and on some level, they seem believable.
But for someone to lose around THREE HUNDRED
AND FIFTEEN million DOLLARS seems next to
But “next to” is they key word here.
Because that’s basically what happened.
Let’s go through the insanely stupid steps
of blowing 315 million dollars shall we?
In 2002, Andrew Jackson Whittaker Jr, who
I can only assume is named after the colorful
seventh President, won the multi-state powerball
worth an ungodly amount of money.
In fact, Whittaker’s ticket was the largest
single winner in the history of the U.S lottery.
His first mistake was turning down the annuity
that was worth the $315 million and opting
for a cash buyout of $170.5 million.
After taxes that was worth about $113 million.
Good God people PLEASE DO THE MATH!!
He then tried to be pretty generous.
After he pledged 10 percent of his winnings
to Christian charities, he also set up the
Jack Whittaker Foundation, using $14 million
of his winnings.
The foundation benefited food, clothing and
shelter to low income families in rural West
Okay, so Andrew’s a pretty nice fella, huh?
No doubt.
But was he smart?
Welllllll, that’s a different story.
While visiting a strip club, he left $545,000
worth of cash in his car.
Who are you, Floyd Mayweather?!
At least Mayweather has recurring cash flows!!
Obviously his car got broken into, and the
money was gone.
So that’s over half a milly gone right there.
Apparently he didn’t learn his lesson because
months later, his car was broken into again
and thieves made off with $200,000 in cash.
Dude, come on, how dumb ARE you?
Sadly things only got worse.
His granddaughter’s 18-year old boyfriend
lied when he OD’d at Whittaker’s house
in 2004.
A few months later the granddaughter also
lied under mysterious circumstances at a friend’s
The case was never solved.
He would go on to be charged with a DUI in
2005, and developed a bit of a gambling habit.
He bounced a 1.5 million check at a casino
in Atlantic City.
And just as icing on the cake, his home caught
fire in December of 2016.
It turned out that he had never insured the
home…so it was a total loss.
No Insurance?
I think my head just exploded.
No matter how well intended he might have
been, Whittaker didn’t manage his winnings
very well,and whatever may be leftover will
soon be gone if he doesn’t get it together!
Now if I had to bet half my net worth on what’s
gonna happen, it’s for sure on him back
to being broke.
Here’s what’s next!

100 thoughts on “The Dumbest Lottery Winners Ever!”

  1. 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…

  2. Do your research on Abraham Shakespeare. You racist fuck. He was swindled by a lady who wound up murdering him. Way to make light of someone's murder. Lottery systems within the USA is targeted to all races from The ghettos to the hollers in WV. Hope you get the likes you channel is pining after. Not finishing this video. Unfortunately stopping the vid has no impact on this bullshit online personality your cultivating.

  3. Hahaha wtf man, if I even had 1 mil I would turn it into more
    Those people are not even thinking.
    What a shame

  4. MY MOTHER: Remember, a fool and his money are soon parted.

    ME: Mom, do Richard Branson, Elon Musk, Jeff Bezos, Donald Trump, or Mark Zuckerberg look poor to you?

  5. 9:55

    One need not be an uneducated, overreligious, West Virginia redneck in order to blow $350 Million. in less than 3 years——-but it helps!

  6. My old boss (a billionaire businessman) had a great phrase… "Money can't buy you happiness… but at least it allows you to be miserable in comfort!" Great guy.

  7. I don't think it is fair to call the first guy 'dumb'

    However Michael Carroll is a POS and an embarrassment to Britain

  8. How is Vivian Nicholson on this list? She didn't win anything. It was her husband and the law said none of it was hers.

  9. Get four professionals in your corner, working with you. A lawyer with a good reputation.. A property manager, if you plan on acquiring a lot of property. A professional personal accountant to handle your finances. And a financial broker or advisor. That's it! Fuck family and fuck friends! Always get annual payouts, fuck the lump sum. If you mess up the first time, you will learn for your mistakes! UNLESS you are that ignorant with no common sense and a poor! I'm done here!!

  10. 1 Take the lump sum.
    2 The winnings are your wealth. Do not spend your wealth. Ever.  
    3 Invest your wealth in normal, boring, sound, everyday investments.
    4 Spend as much of the proceeds from your wealth as you want. Don't use credit to access it early except for a reasonable house payment.

    example: You won $10M! You take the lump sum, and pay your taxes. Your wealth is now $6,400,000. You earn 8% APR on that. That leaves you with a weekly income of $7,400 after income tax. Now go live within your new means. You now make as much as someone who makes $510,000 a year. A $1M house is about right. $150,000 worth of cars is fine if that's your thing. But that's all. Are you surprised to learn that spending more than that on cars is overspending when you just won $10M? Well it is. Want more expensive cars? Don't spend all your investment proceeds. Reinvest. This increases your wealth and changes the calculations. If you double your wealth this way, you can have $300,000 worth of cars and a $2M house.

  11. The stupidest thing people do is : stop looking for ways to save and grow thier income and money, once they have a windfall. All they want to do is spend, and show off and cater to The people that show up with thier hands out. Why wouldn't you simply buy a slightly better shelter, transport. Live your normal life.nunber 2 moron could have put his money in a index fund, wtf lost $350Million what a stupid fuck!

  12. 10mil
    I can do a lot with that
    Set up my kid with 2
    Set myself up 2
    Charity, 4
    2 for just in case. I been around money and none of the granite countertops and giant house and fancy cars just pain in my butt.
    I probably just do a ton of drugs

  13. When talking about Andrew Jackson Whittaker he speaks of West Virginia then shows a map with Virginia highlighted in red. Research much???

  14. Dont tell anyone.
    Lump sum.
    Invest your total winnings in an interest bearing account.
    Live high on the hog off your interest.
    If you cant figure that out, youre a dumbshit and deserve to lose all your money.

  15. But the time value of money principal tells me that money in my hands today is often much more valuable than an annuity paid out over a long period of time… Why you keep stressing the contrary, bro?

    The Americans get their pants pulled down and FUCKED with their lottery,the first guy won 30 million but ONLY GETS 16.9 million WHAT A FUCKING JOKE,here in the UK if it's a 30 million lottery then GUESS WHAT u win 30 fucking million, the American people should revolt stand up for yourselves, it's like the big slots jackpots at the casinos they don't pay u guys the full amount on them either, it's blatant FALSE ADVERTISING if it's a 30 million prize that's advertised then it's your right to demand 30 million all in 1 go so u can invest it how u want
    FUCK THAT,I'd NEVER play American lottery out of principle

  17. Do the Math people? ok the full lottery is based on an annuity at roughly 5% a year so if a lottery jackpot was 300 million the cash value would be 115 million. Take the 115 million and invest in an index fund at 15% and you make 3 times as much then if you took the annuity of 5%. Not a lot of thinking and anyone can do that. Second the return of the index fund is endless as in after  you die your kids will continue to earn the interest endlessly as for the lottery annuity it runs out in 30 years and remember only 5% a year. So Dude talking in the video, you do the simple math you IDIOT!!!!!

  18. Next person who feel like doing something dumb when they hit the lottery just donate the money to me! Thank you.

  19. If i won a SHITLOAD of money i would get the FUCK out of the GODFORSAKEN Country i am living in
    I Would not tell ANYONE where i was going but i would leave one message
    And the message would be…
    F U C K Y O U A L L Y O U M O T H E R F U C K E R S

  20. Do the math?? Having a cash payout today is a much better choice than an annuity. With wise cash management, you will do much better than an annuity.

  21. My American friend – what the fuck do YOU know about Mikey Caroll? You've read the same shit and are spouting the same crap that we In England have all heard before. Instead of repeating bullshit, why don't you do some real research? Mikey was taken advantage of by his so-called "friends", so get your fucking facts right. Third-hand news Is SHIT news.

  22. Number 3 isn't dumb at all you asshole. Just a kind person who gave away their wealth. Nothing wrong with that. There's a difference between giving your money away and going broke because of poor decisions. You seem to me like a selfish and evil person. I'm guessing you've never given a single penny to anyone in your lifetime whether it be a homeless person or a charity. You have no right to judge these people.

  23. You racist son of a bitch Abraham was such a good person that he couldn’t say no to people even if they were takings advantage of his kindness. If anyone won a lottery they would fuckin buy an expensive house even if it’s 2 mill. If you are in a relationship with someone you truly love you don’t keep anything from each other. He was just unfortunate to fall in love with someone like her and lost his life. He’s not stupid he’s a normal guy who lived his life the same way anyone would. Your juss mad you not ever gonna win a lottery

  24. Tbh when it comes to money I won’t tell no one. I wouldn’t even tell my mom until I decided to provide for them

  25. This commentator is a total cocksucker. Everything about this video signifies what's disgusting about humanity

  26. Message to any lottery winners out there …. Before you squander your money/winnings on needless things , Please give me the money to purchase whatever house I am currently living in so I can take better care of my wife , 35 years of marriage and 3 years of that she was diagnosed with Parkinson's Disease and we are struggling… I mean wow I could think of better things to do with large sums of money.

  27. I had a lawsuit settlement that after everything, I received less than 100k. I put that shit into an annuity. I got paid for six year's. Smfh, getting paid every month is alot better than losing half your shit &/or all up front

  28. I had to dislike because of Abraham Shakespeare. What happened to him was really sad, his mental issues were taken advantage of.

  29. When you won lottery, just dont tell anybody. Live like you used to be until you know what you must to do with that money

  30. The real winners here are the people who broke into a car and made over $500k in cash.


  31. Diversifying a lump sum, depending on the payout %, can get you to the same amount as the annuity faster than just taking it. the big issue is managing the money, not the annuity.

  32. A fool and his money are soon partying!

    Lessons to be learned:
    1. Live modestly, a gigantic mansion will come with a gigantic yearly property tax burden
    2. Drive a reasonable car. Sure get a new car or two, but do you really need 7 and do you need to drive Lamborghini's??
    3. Get a professional to help you manage your wealth, set up a budget and live within it.
    4. Find a way to make your money work for you. Start a business, but don't jump into it half-assed. Do some research, learn the up's and down's of the business first.
    5. Once your money is generating more money, your budget can increase accordingly. Aim for having more coming in then going out.

  33. When you mention a state please fill in the correct State you mentioned West Virginia what you filled in Virginia I wonder what you would do with your winnings 🙂 besides pissing off two States

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  35. Abraham Shakepere Should Not be on here. He was robbed and murdered by someone he thought he trust.

  36. dont work for money, just play the lottery, wen you win be happy wile the money last, lol that is not dumb, its a diferent way of living the life.

  37. The narrator first tells you "dont ever let anyone manage your money!" And then later in the video he says, "if you have never handled a large sum of money, higher someone to do it for you"….

  38. my dad was friends with Willie Hurts he was a sex offender also and he opened up a bar business that failed. But my dad isn't dead or a drug dealer he's actually has a k9 dog that tracks humans, guns, and drugs so pretty much the opposite of Willie

  39. If I win the lotto i wont tell anyone. Id Help only close family 4 people and 2 friends. Dish out 10%. Then not one cent to anyone. Id space out my funds for how many years i want it last. And not spend anymore on what ive allocated for each year. And focus on health and family.

  40. My landlord years ago won 20k in a scratch off then signed the whole thing over to me to try and avoid taxes. I cashed it and he gave me 150 off my rent. lol He was 80. Even as shit a person as I am, I couldn't fuck that old man out of his money.

  41. Fucking asshole who made this video how can you say that about abraham did you know him he was FIRSTLY A NICE MAN WHO GOT TOOK ADVANTAGE OF and murdered by some lady who fooled him God rest that man soul for calling him dumbest you pig

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