The DUMBEST Lottery Winners EVER

michael carroll lottery

By now, you’ve probably all heard about this whole phenomenon of lottery winners going broke. And while it might seem unthinkable that someone could blow through multiple millions of dollars just as quickly as they got them, it’s no mystery as to how it happens. Someone who doesn’t know how to handle money suddenly wins the Mega Millions and buys a bunch of houses, cars, boats, and expensive jewelry. And a year later their bank account is a flat zero. 

You know how they could’ve avoided that? By watching the rest of our Ideal Money videos! But, while we can all wrap our heads around spending our millions on living that lavish life of luxury, there have been some lottery winners in history that have defied all limits of stupidity and lost all their money in some pretty astoundingly dumb ways. 

In this article, I’m going to tell you about some of the dumbest lottery winners ever so that if you ever end up hitting the jackpot, you can avoid making the same mistakes. So, strap in; these are the dumbest lottery winners in history. Sorry, guys…

But, before we begin, there’s one thing that pretty much all of these lottery winners have in common, and that’s the lump sum. You see, when you win the lottery, they give you the option to go with an annuity (which is basically just when they give you a piece of the prize every year) or you can go with a lump sum (which is when you get all of the money at once). And the people that opt to go with the lump sum are the ones that go broke in the blink of an eye. 

Alright, now that we’ve established that, let’s look at our first lottery doofus. And, big surprise, this story comes to us from the state of Florida.

Abraham Shakespeare – White Collar Robbery

abraham shakespeare lottery winner

Abraham Shakespeare, who bears no relation to the famous English poet and playwright, was working as a truck driver’s assistant when he hit a $30 million jackpot back in 2006. As most lottery winners do, he immediately bought himself a Rolex, a Nissan Altima, and a $1 million home. Maybe that wasn’t the best fiscal decision, but when you just came up on $30 million, you can afford the finer things in life. 

Where Mr. Shakespeare really screwed up was when he decided to get into business with a woman named Dee Dee Moore. They started a company called Abraham Shakespeare LLC, which was apparently intended to help Abraham write his life story. Who knows? Maybe Abraham had a pretty interesting life. 

Unfortunately, that book never got written. Instead, Dee Dee Moore basically used the LLC as a way to steal all of Abraham’s money. Moore used Abraham’s money to buy herself cars, other expensive things, and even Abraham’s own house! And then, in 2009, Abraham Shakespeare went missing. 

His family had hoped that he just went to the Caribbean to live on the beach. But, when the sheriff started investigating, his body was found in the backyard of a house that was purchased by Dee Dee Moore. Moore was convicted of his murder in 2010 and sentenced to life in prison without the possibility for parole. Rest in peace, Abraham Shakespeare.

It seems the curse of the lottery is all too real. And while Mr. Shakespeare experienced a Shakespearean tragedy brought on by the greed of others, this next lottery winner lost all of her money because of her own stupidity and greed. 

Christina Goodenow – Good Now, Not Good Later

christina goodenow lottery winner

First off, here’s a pro tip for anyone out there that plays the lottery: if you’re going to buy a lottery ticket, which you probably shouldn’t do in the first place because the lottery is a scam, you probably shouldn’t do it with someone else’s money. And you especially shouldn’t buy a lottery ticket with the credit card of your boyfriend’s deceased mother, which is exactly what Christina Goodenow did in 2005. 

That’s right, Goodenow won $1 million in the Oregon lottery on a scratch-off that she bought with her boyfriend’s late mother’s credit card, which, you know, is illegal. And as soon as she received the money, the Feds launched an investigation. And it wasn’t just the stolen credit card that they got her for. She was brought up on charges of theft, forgery, identity theft, computer fraud, violation of parole, and possession of methamphetamine. 

Seriously? How did she think she was going to get away with this? You don’t think you might draw some attention to yourself when you’re running around spending your $1 million? And when you’re flaunting that money that you won with a stolen credit card, at least have the sense to hide the meth! So, unsurprisingly, Christina Goodenow was sentenced to probation and was forced to forfeit her lottery winnings to the Medford Police Department. I guess you could say that crime doesn’t pay.

Now, Christina Goodenow definitely should have kept a lower profile considering that she was committing multiple crimes when she bought that lottery ticket. And this next lottery winner also probably should have kept their head down instead of trying to hit it big with the lotto…

Jose Antonio Cua-Toc – Lots of Dough and Deportation

jose cua toc lottery winner

Now, playing the lottery doesn’t make much sense in general. The odds are terrible and you’re pretty much guaranteed to just squander a bunch of money. But playing the lottery really doesn’t make sense if you’re an illegal immigrant living in the United States. You can’t even legally claim the money if you win! And, yeah, that’s exactly what happened to Jose Antonio Cua-Toc, a native of Guatemala who entered the United States illegally in 2000. 

Cua-Toc won $750,000 in the Georgia lottery. But, since he was an illegal immigrant, he asked his boss, Erick Cervantes, to claim the money for him. Cervantes agreed and, big surprise, he didn’t give the money to Jose. Now, I understand that was not a very cool thing to do on Cervantes’s part. But, as an illegal immigrant, you kind of have to chalk it up to a loss and move on. 

Instead, Cua-Toc decided to sue Cervantes for the money, at which point his illegal status was discovered. He was also put in jail on charges of forgery and terroristic threats against Cervantes and his family. Apparently, he got so pissed off that he threatened to kill them. Jeez. I think it’s safe to say that Jose Antonio Cua-Talk would have been way better off if he had just spent his money on a can of soda or a candy bar instead of playing the lottery. 

Alright, this next story is also another legal blunder. And, this time, it wasn’t between an employer and employee, but a husband and wife. 

Denise Rossi – Divorced and Dead Broke

denise rossi lottery winner

There are a lot of people living in unhappy marriages in the world, but it often isn’t as apparent as in the case of Denise Rossi. After Rossi won $1.3 million in the California State Lottery, one of the very first things she did was file for a divorce from her husband. Maybe instead of saying “’til death do us part” at their wedding, Denise said, “’til I win the lottery do us part.” 

Anyway, Denise didn’t tell her husband that she won the lottery. And so, he was pretty confused when she filed to divorce him pretty much out of the blue. However, her husband eventually found out about the lottery winnings and sued Denise Rossi. And because she had violated California state asset disclosure laws, her husband was awarded every single cent of her lottery winnings. I feel like there’s a lesson to be learned here. Maybe look at your significant other and think: if I won $1 million tomorrow, would I want to share it with this person? Whatever. I’m not a relationship coach.

Up until now, some of our dumb lottery winners have done some pretty bad stuff. But, in the next case, this lottery winner was just too damn generous.

Billie Bob Harrell Jr. – Mr. Nice Guy

billie bob harrell jr

While a lot of the stories I’ve told thus far have been fueled by greed, Billie Bob Harrell Jr. was a generous man. But, as Billie Bob found out the hard way, there is such a thing as being too generous. It took the Lansing, Michigan man less than two years to lose all of the $31 million he won. And he did that by buying cars and homes for his friends and family, by donating extravagantly to his church, and giving to charity. He even donated around 500 turkeys to poor families on Thanksgiving. What a guy!

Unfortunately, while Billie Bob had a kind heart, his financial wisdom wasn’t quite up to snuff. Essentially, a company paid him a lump sum in exchange for his annuity payments, and he pretty much got shafted on the deal. Then, he went through a divorce in which his ex-wife got a ton of his assets, and he was left more or less broke. 

After all that, Billie Bob Harrell Jr. tragically committed suicide. He was quoted saying that winning the lottery was the worst thing that ever happened to him. That just goes to show: money isn’t everything, ladies and gentlemen.

So, from what we can tell, Billie Bob Harrell Jr. was a pretty upstanding guy while he was alive. But, the next lottery winner on this list seems like a bit more of a sketchy character.

Michael Carroll – Party Animal

michael carroll lottery winner

So, what happens when a 19-year-old with a troubled upbringing and a history of petty crime and drug use wins around £10 million in the United Kingdom national lottery? I think we all know where this is going… 

That’s right, Michael Carroll was literally wearing a court-ordered ankle bracelet when he rolled up to collect his winnings. He had also been working as a garbage collector and didn’t even have a bank account, which pretty much tells you that he had no idea how to handle money. After getting the equivalent of around $14 million overnight, Carroll became somewhat of a celebrity in the U. K. 

He bought a mansion, threw legendary parties with drugs and hookers, and even had demolition derbies in his backyard. He was also often seen wearing extravagant amounts of gold chains and other expensive jewelry. Now, I’m all for a good party, but that sounds a little extreme. Not surprisingly, Michael Carroll quickly spent all of his winnings, so much so that he went homeless and ended up living in the woods. Yikes.

Eventually, Carroll was able to get a job at a cookie factory making $300 a week, which sounds like a pretty far fall from the lifestyle he was living before. Apparently, though, Carroll was able to kick his drug habit after going dead broke and he says that his lifestyle now is far more satisfying. I guess that’s some sort of silver lining…