The Biggest Gambles In History

 -Betting Stories and Betting Coups


Sports betting can be a lucrative venture for people who play their cards right. Betting on sporting events like football is increasingly common, with almost 50 percent have placed a bet on a sports events

Although the world is likely littered with enough losing betting slips to account for a couple of forests, there have been multiple occasions where, either by hook or by crook, huge winnings have been taken from the bookmakers – even bankrupting a few along the way.


Here we have collected some of the world’s betting coups in history.


1. Archie Karas

Archie Karas was one of those ‘rags to riches’ stories. As a kid, he already wanted to help his family. He wanted to bring in some extra money by hustling the kids in the playground. On the side, he would regularly bet on a game of marbles, where he would usually emerge victorious. His father worked in construction. His relationship with his father was always strained and their financial situation didn’t help at all.

As their financial situation worsened so did his relationship with his father. It became violent. At that point, he decided that he wanted more from his life. He left his home and set his sights in the United States.

Karas worked for two years as a waiter on a ship so that he earned enough money to be able to move to the US. He landed in Portland, Oregon and then hitchhiked to Los Angeles. There he took another job as a waiter at a joint next to a bowling alley. There his career in gambling started.

At the back of the bowling alley, there was a poker room and some pool tables. It was something new to Archie but it did not take long for him to master both. Soon he spent several hours honing his skills and hustling the other locals. His stint was up and down. Eventually he ended with $50 dollars in his pocket.

In Las Vegas, he started out with just $50 and he knew he wouldn’t go far with it. He loaned $10,000 from a friend and that set him on his way. By the end of the night, he made $20,000 and repaid his friend and even gave him the extra $10,000.

Soon Karas got the attention of big-time poker players such as Stu Ungar, Chip Reese, Doyle Brunson, Johnny Moss, and Puggy Pearson. All of them lost big time to Karas. At the end of his poker run, he had amassed $17 million.

From poker, he made a jump to craps. At first, he started well and his money kept growing. But his luck eventually ran out. He lost around $11 million in just a short period. He tried to recoup his winnings by again taking on Chip Reese, who got back at him that time around.

But all good runs must come to an end. After switching to baccarat, Karas lost almost $40 million. He was banned from setting foot in casinos due to a series of scandals, which includes marked cards. He was blacklisted in Nevada casinos and never set foot in one again.


2. Yellow Sam Coup (1975)

Yellow Sam is a racing horse owned by Irish former band manager turned gambler Barney Curley. In what went down as the most famous betting coup in British or Irish horse racing history, Curley entered Yellow Sam in a National Hunt race at a small provincial track in Bellestown, Ireland. He intentionally targeted the course because it was only serviced by a public call box.

To ensure that his horse went off at generous odds, he had Yellow Sam run in a series of races with conditions he described as unfavorable. He had the horse run over distances he knew would not particularly like.

On the day of the race, Curley had his runners dispatched to several bookmakers with sums of money ranging from £50 to £300 wagered for Yellow Sam 10 minutes before the race. As bets started to pile up to more than £15,000, it was panic time for most bookies and contacted their representatives at Bellestown to bet on Yellow Sam.

By doing so, the starting price of Yellow Sam would be slashed and their liabilities would be greatly reduced. However, their efforts went for naught as the sole telephone was being hogged by a distraught racegoer who was having a final conversation with an aunt who was dying in the hospital.

The man was Benny O’Hanlon, a friend of Curley. The dying aunt was not real and was only designed to hold up betting agents waiting to use the phone until Yellow Sam had won the race by two-and-a-half lengths at a ridiculously generous odds of 20-1.

Curley’s profits for the day reached £300,000, which is equivalent to £1.4 million when adjusted to current inflation rates. Curley used the money to buy stables. His latest big money coup was pulled off in January 2019 when he arranged four horses from 3 different stables to win on the same afternoon. He again caned bookies for a whopping £2 million.



3. Hole in one gang (1991)

Paul Simmons and John Carter were Essex men who had experience in the bookmaking industry. They toured the UK and Ireland searching for independent betting offices who would give them odds on a hole in one being scored in five different tournaments namely British Open, Benson & Hedges, the Voice PGA, US Open, and the European Open. They got a 100-1 on a hole in one happening at the five events mentioned in a wager that should have cost at 30-1.

Remarkably, at least one hole was scored in all five tournaments with Spanish viveur Miguel Angel Jimenez winning it for Simmons and Carter at the European Open at Walton Heath Surrey. The Essex duo brought home more than £500,000 excluding the winnings they were not able to collect from 12 different bookies who did not pay up on grounds that they were bankrupted by the pair or was not able to renew their licenses for mysterious reasons.


4. Fred Craggs: 50p millionaire (2008)

On the eve of his 60th birthday, agricultural agent Fred Craggs from North Yorkshire started a 50p eight-horse accumulator. It was started by the racehorse called Isn’t That Lucky and finished by A Dream Come True. All eight horses came in at combined odds of more than 2,000,000-1 leaving Craggs to rue on the 10p he wasted on the bet. His winnings were capped at £1m instead of £1.4million.

Another ruling at the William Hill small print could have capped his winnings at £100,000 on grounds that his other horses had been participating in overseas races.


5. The 6,479-1 novelty bet (1989)

While the name can be deceiving, novelty bets can be a lucrative source of income for both bookmakers and customers. In their desire to part as many punters as possible from their money, bookies will offer odds on things like the weather, religion, politics, reality shows, talents contests, and anything else under the sun. Although the stakes are quite limited, the potential for reward can be huge.

In 1963, a man named David Threlfall placed a £100 bet at 100-1 odds that a man would walk on the moon before the end of the decade. He collected £10,000 in winnings with still six months to spare. However, he wasn’t able to use that as he was killed in a crash in a sports car that he bought from his winnings.

In 1989, a 40-year old rune reader placed a £30 accumulator in his local bookies in Newport, South Wales on a series of happenings before the turn of the century: Cliff Richard would be knighted (4-1); U2 would be a going concern (3-1)as well as the soap opera EastEnders (5-1), their Australian counterparts Neighbors (5-1) and Home and Away (8-1) would remain on British screens. All five events happened and the man’s 1,679-1 odds netted him £194,000 in total winnings. After a couple of days of confirming, the bet went down as the biggest novelty bet in bookmaking history.


6. D Four Dave (2010)

In June 2010, a horse named D Four Dave emerged victorious in a low key handicap hurdle race held at the small course of Kilbeggan in the Irish midlands. Despite being available at 14-1 earlier that day, race odds were at 5-1. It was discovered that the horse was part of an enormous gamble perpetrated by one of its part-owners, Douglas Taylor and 200 unwitting assistants.

The assistants were sent off to 200 different betting shops around Dublin and Kildare. This greatly minimized their chances of winning more than 200,000 should their horse prevail in a “bad race.” Although D Four Dave won as expected, Taylor’s efforts landed those behind it considerably less than the amount they hoped for.


7. Slippery characters at Sheffield Greyhound track (1996)

In January 1996, organisers of an evening race at the Sheffield greyhound track attempted an ingenious scam by reflooring 5 of the 6 starting traps with shiny new rectangles of Formica laminate. Knowing full well that a greyhound who could start fast will have a huge advantage, the scammers left trap no. 2 untouched giving the dog wearing the blue jacket a huge advantage while the others would be left eating their dust.

Unfortunately, the plan was discovered before the start of the evening race. The Formica was removed and racing went on as usual. The first two races saw the dogs in trap no.2 emerging as favourites. But by the third race, no one showed little or no interest to bet on the dog in trap no. 2.


We hope you have enjoyed this trip down memory lane as we took a look at some of the biggest and most impressive betting coups and wins in history.

Did we miss a great story? Let us know in the comments below.


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