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
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
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
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
Expensive cars, fur coats, lavish vacations,
a huge ranch style home and a spectacular
lifestyle that quickly caused their fortune
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
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
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
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
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**
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?
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
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.
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!