The Best And Worst Gamblers You’ve Never Heard Of

Those involved in the gambling world, whether through blackjack, poker, horse racing or sports betting, are familiar with the superstars of these industries, from expert poker players like Jason Mercier and Chris Moneymaker, who made millions playing the game, to the blackjack stars such as Ken Uston and Ben Mezrich, who terrified casinos back in their day. But what about those who are less well known, what about the celebrity gamblers, the bad losers and those who made the headlines not because of their skill or their luck, but because of their sheer stupidity?

These are the names that most people have either never heard of, or simply don’t associate with gambling, but that have made a big impact on the gambling world in one way or another, and have made the headlines for their gambling despite not winning the big tournaments.

Small Stakes; Big Wins

This anonymous gambler’s good fortune was revealed by William Hill bookmakers, who he took for half a million pounds, which equates to around $800.000. They didn’t release his name and the gambler himself didn’t come forward, but he is believed to be a Manchester United fan who spent his time gambling on football matches.

You may think that £500.000 is not a lot of money on the face of it, certainly not compared to some of the other names on this list, but this anonymous Red Devil’s fan makes it because of the money that he staked in order to win that amount, all 50 cents of it. The bet was a twelve-fold accumulator that returned odds of over one and a half million to one. There are also reports that the same gambler scored another huge accumulator years earlier, netting half that amount with a bet that totalled around $5, and ensuring that he can retire on his winnings and spend the rest of his days as a full time small-stakes gambler.

What are the Odds?

Another anonymous gambler who loved his soccer was a Tottenham Hotspur fan who watched his side take a 3-0 lead over Manchester United before half time. He was with a new girlfriend at the time and in an effort to show her how brave and “wild” he was, he remortgaged his house and staked the lot on Tottenham winning the game.

The odds were well in his favour because although Manchester United had been the favourites to win before the kick-off, it seemed highly unlikely that they would be able to overturn such a deficit. This supporter saw it as an easy bet, something that wouldn’t return great odds but, considering how much he had staked, would give him enough to pay off that remortgage and then to splurge on his new girlfriend and impress her even more. Unfortunately for him, though, Manchester United had a habit of refusing to give up and of turning over large deficits, and in the end they won the game 5-3. This unlucky fan not only lost his house, but also his girlfriend.

Charlie Sheen

Most people have heard of Charlie Sheen, especially since his highly publicised antics following his dismissal from the Two and a Half Men television program. Two and a Half Men was a sitcom in which Charlie Sheen played a man named Charlie who did little but drink, smoke and gamble on sports all day, and as it happened that wasn’t far removed from Charlie’s actual life.

His ex wife, the glamorous Denise Richards, who appeared on the Two and a Half Men show for a number of episodes, reports that her ex husband used to spend up to $20.000 a day betting on sports. Like every gambler out there he also enjoyed playing cards, including poker and blackjack, and was happy to gamble on pretty much anything.

John Hennigan

John was obsessed with gambling, as is the case for many people on this list. He spent every free minute of every free day playing cards, pulling slot machines and throwing his money at roulette tables. You’d be hard pressed to find a man who loved gambling as much as John Hennigan. His friends knew this and decided to place a bet of their own.

They bet John that he couldn’t live in a fairly remote area of the United States where gambling was outlawed. The bet was $100.000 and we’re not talking about some faraway, ice-cold place where no human has ever set foot, but rather Des Moines, Iowa. A bustling city where life may be quieter than it is in Vegas, but it is far from dull. It seemed like an easy bet to win and one that many would jump at the chance of taking, but John Hennigan didn’t even make it two days before he packed ups and rushed back to Vegas, $100.000 lighter than when he left.

Tiger Woods

The golf superstar is another well known name that regularly takes to the casinos to gamble away his hard-won fortune. Tiger is a big fan of blackjack and it has been reported that he gambles up to $25.000 on single hands. It is unlikely that you’ll find him tossing chips at your local casino, but if you head for the VIP areas in Florida and Vegas, then you might just bump into him.

Matthew Etherington

Matthew Etherington is not a name that many will recognise, certainly not outside the United Kingdom. Matthew is a soccer player, having been on the books of clubs such as Stoke City and West Ham United who play in the English Premier League.

During his West Ham days Matthew developed a gambling habit that would see him blowing tens of thousands of dollars on a weekly basis. Because professional sports stars are not allowed to bet on the games that they play in, and because gambling by the players is generally frowned upon, his hid his antics from everyone around him. He also says that he didn’t bet on soccer games, instead sticking to horse racing, greyhound racing and poker.

Over the course of several years, Matthew Etherington lost over £1.5 million, or around $2.5 million, and fell into debt before deciding that he had a problem and needed to seek help.

Steve Richards

One of the most daring, stupid and unfortunate gambling stories in recent years comes out of Wales in the United Kingdom and involves a roofer named Steve Richards. The 56 year old was a big gambling fan, but as he didn’t have a lot of money to throw away he tended to stick to £10 and £20 bets here and there.

As is the case with many other people in Wales, rugby was Steve’s sport of choice and one week he managed to win close to £40.000 on a single £10 bet, bagging himself a 12-fold accumulator. For many in Steve’s position this would be a life changing amount of money, and one that would see them running to the bookies to cash it in and bank it immediately, but Steve had other ideas.

Steve took the money he won and put it on his team, Wales, to beat Australia. He only would have won an extra £20.000, but as it happens Wales were beaten by Australia and Steve lost what was probably a year’s wages in less than an hour and a half.

Easy Money

Another bet that seemed a dead cert was made by an equally unlucky punter who also lived in the United Kingdom. As he watched a television match between Angola and Mali, which Angola led 4-0 with just over ten minutes to go, he saw that the bookies were still taking bets on live-play. The odds for an Angola win were as low as they could go, which you would expect, but he saw it as a dead cert, so any bet was a good bet in his eyes.

The unlucky gambler threw all of his life savings on an Angola win. He only stood to win £44, but it looked like the easiest £44 he would ever make. But, the gods weren’t smiling at him and in fact seemed to be poking him and laughing at him, because as soon as he placed the bet Mali pulled a goal back, and a few minutes later they scored again to make it 4-2. The bet still looked likely as the ninety minutes were up and the game went into a few minutes of injury time, and no doubt the punter removed himself from the edge of his seat and gave his fingernails a break, but then two quick goals from Mali squared the game up and with a final result of 4-4, he lost everything that he had.

Mark Johnstone

Mark Johnstone, a 52 year old businessman was looking forward to a weekend of fun in Vegas, sipping free drinks and splashing the cash on the table. Unfortunately, he drank a little too much and a few dollars quickly turned into half a million.

Mark claims that he was incredibly drunk and that the casinos continued to serve him despite this fact (which they are not legally allowed to do) but this seems like the cry of a hopeless (and broke) man.

Nick Leeson

Nick Leeson is best known as the man who ran away with close to a billion pounds sterling from Barings Bank, all of which was his customer’s money. He was one of the top financial traders for the bank after scoring some nice gains for them early on in his career, but then the losses began to pile up and the trade turned ugly.

Many know the story of Nick and of his troubles, but what many people might not know is what happened to the £800 million that Nick took. Like a true gambler, and a bad one at that, Nick decided that if he could go double or nothing then no one would be any wiser and he could get back to working as a profitable trader. So he took the money to a casino and dropped it all on a spin of the roulette wheel.

To be fair to him it was a 50/50 chance, and in a parallel universe his problems may have been over, he may have gone on to be one of the best traders in the country and Barings Bank may have still been alive and well today, but in this universe Nick Leeson lost all of the money, his wife left him and he was sentenced to nearly 7 years in prison.

Terry Watanabe

Terry Watanabe, a businessman who was born and raised in Nebraska, was a man who liked to gamble and who was also well liked by the casinos that he frequented. Terry wasn’t just a whale, he was a lovecraftian-esque whale the likes of which very rarely grace the casino floor. A whale is someone who bets thousands upon thousands on single hands, and has the money to do so. It is generally not someone who knows what they’re doing, someone who is a master at card counting, but is someone who plays the games that the house control and is happy to watch his fortune dwindle away.

But Terry wasn’t content with losing thousands and in a short space of time he managed to lose over $200 million at Harrah’s Casinos in Las Vegas. Some casinos, even in the City of Sin, earn those sort of profits on an annual basis, so there’s a good chance that Mr Watanabe did more for the Vegas economy that year than any other individual in the city.

To lure this gambling fan into the casino Watanabe was given half a million dollars to spend at the gift shops, and all of his airfares and other expenses were paid for. He was even given free tickets to concerts and shows, and offered a 15% rebate on all of his losses, which equated to a considerable amount by the time he had finished.

Watanabe preferred roulette and slots to the other big-spending games, but he also played a lot of blackjack, although he didn’t really know how to play. On some days he would gamble for 24 hours straight, and his low skill level and compulsive nature meant that it wasn’t long before he racked up his colossal bill.

Harry Kakavas

Although he is a hard man to follow, there is one gambler who managed to top Terry Watanabe’s losses. Harry Kakavas made his fortune in the property industry in Australia, and he showed off this wealth when gambling and losing over $160 million in under 6 hours, playing $300.000 per hand of blackjack. As with Mark Johnstone though, Kakavas’ lawyers are claiming that the casinos took advantage of him when he was in a weakened state. His legal team claim that he has a serious issue and that the casinos exploited this for a profit.

Over the course of a number years, Harry Kakavas lost an amount that has been reported to be as high as $1.5 billion, which was no doubt most of, if not all of the money he made from his property empire. In fact, there are suggestions that he was forced to borrow a couple of hundred million dollars from his friends, family and coworkers in order to continue gambling, all of which added to the vast sum that he lost over the years.