If you’ve ever gambled, it’s a near certainty that you’ve suffered plenty of crushing losses. A dramatic last second layup that leaves you one-point shy of covering, that garbage time touchdown that pushes it from the under to the over, the dealer somehow getting a blackjack on your biggest hand…the list goes on.

• Gambling Addiction Stories Women
• How To Deal With A Gambling Loss
• Compulsive Gambling Stories

Carolyn Crawford went to prison for stealing from her employer to support her pokies addiction, and now shares her story to encourage others to seek help for gambling harm. Gambling Horror Stories: The Worst of the Worst. Tommy Four Fingers Goes All in. Tommy Four Fingers dreamed of being a high roller. The only problem: he could barely count, struggled with basic math and didn’t really have the worldly sensibilities necessary to be able to understand the nuances of human emotions. I'm a gambling addict. Three years ago, I was convicted of white collar fraud, after I stole over $130,000 from my employer to fuel an insatiable addiction. Only gambling losses. The IRS does not permit you to simply subtract your losses from your winnings and report your net profit or loss. And if you have a particularly unlucky year, you cannot just deduct your losses without reporting any winnings. If the IRS allowed this, then it's essentially subsidizing taxpayer gambling. 11 of the biggest losses casino dealers have ever witnessed. #1 – $10 million over three weeks. “I worked in a large casino NOT in America. We had a lot of Asian clientele in our VIP room. Once had a guy betting. #2 – $9 million in one night. #3 – $720,000 in five.

If you feel like you’ve been a victim of bad betting karma, you aren’t alone. In this article, I’ll lay out 5 examples of betting losses that will help you feel better about your own.

1 – The GOAT Goes Down

Michael Jordan is undoubtedly (sorry, LeBron people) the greatest basketball player of all-time. His relentless competitiveness was an invaluable asset for his game throughout his career. Unfortunately, this same competitive spirit didn’t always help outside the lines.

A golf-lover and gambler, Michael Jordan was known to wager huge amounts of money on the course despite not being the most talented player. His betting buddy Richard Esquinas recounted one time he’ll remember more than any other.

How did he get down that much in the first place? By placing historically-high bets on each hole, of course. It’s been said that it was no big deal for him to throw down $100,000 on a single hole.

While MJ never backed down to anyone, perhaps golf was not his best game. As it stands today he’s worth more than a billion dollars, so I’d say he can lose a few more $100,000 holes and still come out okay.

2 – Rap Battle

Long-time producer, music executive, and rapper Birdman is an avid sports bettor. Unfortunately for him, betting on the Super Bowl has been somewhat of a challenge.

As a New England Patriots fan, he certainly had good reason to be feeling confident about his chances going into Super Bowl XLVI. He was so confident, in fact, that he was prepared to put down $5 million on the game. One sportsbook challenged him to do it but he backed down.

Instead, he placed a $1 million wager on the game. This time he didn’t place it with a sportsbook, but rather went head to head with fellow rapper 50 Cent.

The game ended with a New York Giants victory and 50 Cent took the million from Birdman. And his bad luck did not stop there.

In Super Bowl LII, which featured the Patriots and the Eagles, Birdman challenged another rapper to raise the stakes. He bet AR-Ab $100,000 that the Pats would take down the Eagles.

Of the many comeback drives Brady put together over the years, this would not be one of them. Birdman lost the $100k, and presumably has stopped betting other rappers.

3 – The Whale of Whales

Over the years I’ve read about plenty of high-rollers who have suffered big losses. These people are the ones who keep casinos in business, and the ones who act as a warning to others that gambling can end very badly.

One such man was Terrance Watanabe. An American businessman who had developed quite the fortune, in the hundreds of millions, also had a penchant for taking risks in Las Vegas. Unfortunately for Terrance, he wasn’t a very good gambler.

Most casino whales prefer to play games where some skill is involved, such as blackjack or baccarat. Not Terrance Watanabe. He actually preferred to wager his money on games that were purely based on chance.

Casino management, who were probably his biggest fans, referred to him as a “house player.” This means that he actually liked playing the games that had a higher house edge. Meaning he was betting on games that he knew were tipped in the casino’s favor.

Now before I get into the exact dollar figures Mr. Watanabe burned through, it’s important to get some context on his mindset during all of this. Today, he claims that he is a compulsive gambler, and that casinos like Caesars Palace knowingly took advantage of him and his condition.

Additionally, he has alleged that casinos provided him with drugs and alcohol in order to keep him gambling, and losing, as long as possible. Somewhat surprisingly, the gambling regulators actually took his side and fined Caesars Palace $225,000 for their misconduct.

That fine might seem significant, but when you consider the amount of money Terrance Watanabe lost, it’s a drop in the ocean. The final total of his losses added up to nearly $112 million per the Wall Street Journal.

4 – Vegas Dave

With a nickname like Vegas Dave, one has to assume that big losses are just going to be part of the experience. This sports bettor, whose actual name was Dave Oancea, was known for being showy with his gambling on social media.

Unfortunately for Vegas Dave, he was about to get a big dose of harsh reality in 2016. He took a $1 million bet on female MMA fighter Miesha Tate at UFC 200. As Tate squared off against Amanda Nunes, things went south quickly for both Tate and Dave.

It only took a little more than three minutes for Tate to fall to Nunes, costing Dave a cool million dollars. Following the defeat, his social media posts seemed to focus more on his concern for the health of Tate, who had broken her nose during the fight.

I’m sure that playing off a million dollar loss as the second thing on your worry list sounds good, but my guess is that the loss hurt more than any broken nose.

5 – The Daredevil

The betting losses described above are significant, but ultimately nothing that really surprises anyone. To find something a bit more unique, let me take you back to the good old days of 1883.

Daredevil, and self-professed compulsive gambler Matthew Webb had built a name for himself after becoming the first man ever to swim across the English Channel.

Webb was unique in that he was able to make enough money to support himself by betting against the public on swimming challenges that he would perform. For example, he once won a bunch of money by swimming for 74 hours straight.

Although he was British, he spent quite a bit of time in America as well. In 1881, he took up residence in America and won a few challenges that paid him fairly well, but it wasn’t quite enough to fully support himself at that time. So, he did what any reasonable gambler would do – he put his life on the line and bet on himself.

This time, he decided to take bets on whether or not he could swim through the whirlpool found at Niagara Falls. The dollar figure he would receive if able to complete the challenge was $10,000. Keep in mind this was pre-1900, and that amount of money was enough to last him awhile. It would be roughly worth $400,000 today.

On July 24^th, 1883, Webb dove in to attempt the challenge. He was never seen again.

Conclusion

As long as gambling is available, you can bet there will be individuals who are willing to risk it all in hopes of a huge payout. In Matthew Webb’s case, he paid the debt with his life.

These examples of extreme gamblers should make everyone else aware just how quickly things can turn for the worst if you aren’t careful. My guess is that these people weren’t exactly keeping a close eye on their bankroll.

Although you probably won’t ever have $100 million to lose, let these people be a cautionary tale to always bet within your means.

Updated September 04, 2017 16:45:46

I'm a gambling addict. Three years ago, I was convicted of white collar fraud, after I stole over $130,000 from my employer to fuel an insatiable addiction.

My poison of choice was not poker machines, but online gambling.

Racing, the thoroughbreds, the trots, the dogs — I wasn't fussy, so long as I could get a bet on and fuel that addiction.

The bets would range anywhere between $5,000 and $20,000 a day. I would bet until 3:00am, try to sleep for three hours and bet again for another three hours on online racing in the United States.

I always thought the stereotypical gambling addict was a working-class middle-aged man or woman, sitting at their local club, feeding their favourite pokies machine four or five nights a week.

But I rarely ventured into the local TAB.

Betting while the kids were in the bath

Gambling Addiction Stories Women

At the zenith of my addiction, I was married with two beautiful young children and working as a finance manager at a local council.

When I was with my family, I was physically there — but mentally, I was miles away, thinking about gambling: when I could next bet, where would the money come from, whether I could back a winner.

I thought about gambling 24/7. I placed bets at home, at work, the shops — basically everywhere and anywhere I could get reception on my phone.

I would be walking with the kids and our dog, yet I'd still be trying to place bets. I would even bet and watch the races on the phone while the kids were in the bath.

A knock at the door

I had been thinking about stealing to solve some of my debt problems for months, but I couldn't do it because I knew the consequences would be dire.

Then one evening, I had a visit from two large men with a baseball bat, strongly suggesting it would be in my best interests to repay a sizable debt that was due that week.

They punched me and threatened to use the baseball bat 'next time'.

I was left bruised and battered from their warning. It was a seriously scary moment; I still occasionally have flashbacks and it sends chills through my body.

That night, I made the decision to steal from work. I felt physically sick and fidgety; my mind wouldn't stop racing. I knew it was wrong, but I did it — knowing I could one day get caught.

The first time is without a doubt the hardest — but once you've done it, stealing becomes easier.

Listen to the program

I had nothing to lose. That's how I 'reasoned' it.

However, stealing became another problem to add to my list.

I was constantly worried about being caught. When someone knocked on my office door, when I got a phone call, when my boss called me to a meeting, I was never quite sure.

The fear was slowly killing me, but I couldn't confess, couldn't turn back. I was on a knife-edge with no solution, no way out.

It was a Monday morning when I was finally caught. I was called into the CEO's office and they presented me with the overwhelming evidence.

I was caught red-handed, but I still denied it. I knew my career was over and that jail was not far away.

But at that stage, I had a small sense of relief. No more looking over my back. The lying and deceitfulness could stop.

On the inside

When I was caught and sentenced to jail, the gambling addicts I met in the prison system had similar stories to mine. They were middle-aged, smart, well-educated men from good upbringings, all addicts to racing and not the pokies — certainly not the stereotypical gambling addicts I had imagined.

My addiction cost me everything. I lost my job, all my material possessions including house, car, everything I owned.

But that pales into insignificance to the lost relationships.

Need help or support?

• Call Lifeline on 13 11 14

My marriage disintegrated, I lost access to my children, I don't talk to my family and I'm no longer on speaking terms with most of my friends. I don't blame them.

During my year in jail, I had enough time to reflect on all the damage it had caused and when I was to be released I knew I couldn't go back to that lifestyle.

You get far too much time to reflect in jail. I was constantly thinking about the kids, but I didn't decide to quit gambling because of them. The constant stress and 24/7 of thinking about gambling had destroyed me: physically, emotionally, and financially.

I knew if I didn't stop gambling it would kill me.

Get help before it's too late

I write this not because I find it a cathartic experience, but because I hope that it helps others to seek help before it's too late. Or for family and friends of addicts to intervene and offer support.

How To Deal With A Gambling Loss

For people 'on the edge' or thinking about committing fraud, the solution is simple: get help.

Seek support before you hit rock bottom. The help that suited me the most was from my psychologist, one-on-one extended chats — but for others it may be Gamblers Anonymous.

For the family and friends of addicts: please don't give up on them, it's a horrendous disease and they need all the support you can give.

Life in 2017 is certainly not perfect, but it's a damn sight better than it has been.

I've got regular access to my children, I'm rebuilding lost relationships, I've found some temporary work — and I haven't had a bet since 2014.

Topics:gambling, internet-culture, family-and-children, fraud-and-corporate-crime, law-crime-and-justice, australia

Compulsive Gambling Stories

First posted September 04, 2017 12:14:41