The Nassau is three bets in one: low score on the front nine, low score on the back nine. A while back, VegasMaster held a contest asking our global readers to provide us with their best gambling stories. In response, we received some of the most bizarre, funny and craziest gambling stories, ever! We selected the best ones for you to enjoy. You won’t believe some of the real-life experiences our readers from all over the world.

This list was originally published in January 2010, last update was January 2020, let is know in the comments if you think anyone should be added.

Phil Bull

Phil Bull made a massive amount of money from betting, but not only was he a successful gambler he was also a breeder, owner, writer and publisher. It is estimated he made millions during his career.

In 1948 he launched the now internationally renowned organisation Timeform.

Phil had a shrewd attitude towards betting. He looked at the season as a whole and his form study was the same for every race.

How To Make A Book by Phil Bull
Phil Bull: The Biography by Howard Wright

JP McManus

Multi millionaire JP McManus is a renowned gambler and race horse owner.

Originally from Limerick in Ireland, McManus started betting as a schoolboy before working in his family’s plant hire business. He had his own betting stand for a while at Limerick’s greyhound track and it wasn’t long before he moved into owning horses as well as betting and laying. These days JP owns the largest number of National Hunt’s horses.

His first ‘big’ win (rumoured to be around £250,000) was at Cheltenham with a horse called Mister Donovan who was 2nd favourite but ended up winning the race. He also won over £1 million from famous Scottish bookie Freddie Williams in 2006 at Cheltenham.

Although McManus is a high level gambler a large part of his wealth is said to have come from international financing and money dealing which he overseas from his base in Geneva.

Still a big player and maybe he should be at the top of this list as he is still very active. If there is a book to read about JP let me know in the comments, I’d love to read it.

Alex Bird

The late Alex Bird made a considerable amount of money from betting after the war. It is estimated he had an annual turnover of £2 million from gambling.

His interest in gambling began when he was a child. He learned a lot from his father who was a bookmaker. However, he decided there was more money to be made from the other side and he become one of Britain’s most well known professional punters of all time.

Bird had several methods for getting one over on the bookies but his most famous was probably his success on betting on photo finishes which in those days took about 5 minutes to develop. This process earned him a fortune over a period of around 20 years and only stopped when the modernisation of technology meant there was no longer the delay in photo developing.

Alex Bird made his own mind up when it come to betting and rarely listened to anyone – he stuck to his rules and systems. Even now, almost 30 years after his death, there are current systems available that are based on the practices he used.

His biggest bet was on the well known horse Mill Reef at Gimcrack. The season after this Mill Reef won the Derby, again backed by Bird who had by then backed 7 Derby winners in 8 years.

One of his last bets was on a horse called Final Shot in 1990 when it won the Ayr Gold Cup.

Patrick Veitch

Patrick Veitch is one of Britain’s most successful gamblers who has won over £10 million from betting.

At just 15 years of age this mathematical genius got a place at Cambridge although he never completed his degree, instead he turned to gambling and started his own tipping line.

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By his mid 20s Patrick Veitch was already making a lot of money but then came a turning point in his life. He become the target of a criminal and was forced to live in hiding for many months putting his career on hold and leaving him broke. However, following this episode he become more successful than ever and was soon making £1 million a year from his strategic betting methods.

Veitch is a strong believer that there is no short cut when it comes to betting – the only way to win is by working hard at it to get it right.

It is very rare to see Patrick at the races. He uses agents to place his bets and spends most of his time watching and analysing events from his computer.

Harry Findlay

Harry Findlay is a larger than life gambler who has not only made a fortune but also lost a fortune from gambling over the years.

He has always had a love for greyhounds and worked with them for a while after leaving school. Then aged just 20 Findlay spent 11 months in prison convicted of credit card fraud.

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These days bets from his home office which is fully equipped with a number of TV screens and monitors often with different sporting events on at the same time.

As well as being a professional gambler Harry is also an owner. He jointly owns the 2008 Cheltenham Gold Cup winner, Denman who also won two Hennessy Gold Cups. Big Fella Thanks was another of his co-owned horses who he named after his beloved greyhound 1999 Coursing Derby winning Big Fella.

Barney Curley

Barney Curley is a professional gambler and trainer from Northern Ireland who has a reputation for being one of racing’s most colourful characters.

During his childhood he watched his Father run up huge gambling debts but still took up betting himself.

In 1975 he famously organised one of the biggest betting scams of all time – Yellow Sam which made him over £300,000. He has also appeared in court for illegal lottery after raffling his mansion for £1.5 million.

More recently Barney organised big coups in 2010 and 2014 and 2016.

Terry Ramsden

Terry Ramsden originally made his fortune from investment company Glen International in the 80s. He was worth millions and, amongst other things, owned a string of race horses.

He was also well known for his betting and in 1985 won £2 million on one horse. The following year he had another big win on Motivator in the 1986 Coral Golden Hurdle Final.

Towards the end of the 80s however, Ramsden’s company collapsed and he started losing massive amounts on bets – he reportedly lost £1 million on one bet alone. This lead to him going bust at which time he fled to America. He had won but also lost millions of pounds.

In the late 1990s he was jailed for concealing assets during his bankruptcy – one of which was rumoured to be a £70,000 plus win on the horses.

Despite returning to public life a few years later Ramsden has failed to recreate his earlier success and has since been involved in a number of arguments over money.

Pro gambler or rich man who lost it all on the horses? Many think the latter but he was a big player all the same.

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Dave Nevison

Dave Nevison became a professional gambler in 1993 after he lost his job working as a currency trader in the City.

He now has an estimated six figure income made up largely from gambling but also from journalism columns he writes. Dave has also written 2 books and has his own horse racing tipping service.

A Bloody Good Winner: Life As A Professional Gambler by Dave Nevison
No Easy Money: A Gambler’s Diary by Dave Nevison

Alan Potts

At the age of just 14 Alan Potts started betting on horse racing and become a full time professional gambler after being made redundant from his office job in 1991.

He has admitted it took him many years to become a regular winner and despite making an estimated £50,000 a year from betting in the past, he has also suffered losing runs. Although he is also an owner, author and pundit Potts’ main source of income is from gambling.

In 1999 he jointly formed The Golden Anorak Partnership and this is the banner under which his horses now run.

Alan has written 2 books and also wrote for the betting exchange WBX until it closed in 2015.

Against The Crowd by Alan Potts
The Inside Track by Alan Potts

Clive Holt

Legendary punter Clive Holt was first shown that money could be made from betting by his father who kept a couple of greyhounds during the 1960s.

In the early part of 1975 Clive decided he was ready to quit his job working for the Electricity Board and take up gambling on a full time basis.

He started out using a fairly random approach dictated by his finances and he kept no proper records of bets he had placed. He soon made the decision to start recording his bets and this was the first of two business methods he implemented in order to make a better profit. The second was to setup a betting bank.

His first bet was £67 to £30 on Western Jewel who won comfortably and within 6 weeks he had made more money than he was earning in a year working in electricity. Over the years, although rarely winning more than £1,000 at a time, Holt’s profits from betting provided a lifestyle of luxury cars, exotic holidays and a listed country house with acres of land.

A number of books have been written by Clive Holt who was also the man behind Fineform.

Profitable Winners Always Back Winners
Be A Successful Punter
Fineform Winners Guide
Profitable Betting Strategies

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Although some bettors bet for fun and entertainment purposes, there are plenty out there that want to make a living from betting. During our most recent Discussion Day on Twitter, we offered our help and the expertise of various betting experts to those who wanted to know what is required to be a professional bettor. Read on to learn more about the advice that was shared.

Anyone serious about betting knows that it takes time and dedication to become a professional bettor. Building expert knowledge of a sport and gathering enough funds to invest in betting full-time is merely the starting point of making a career out of beating the bookmakers.

Even if you have access to information that others don’t have, a refined strategy that has been rigorously tested and a carefully calculated staking method, there is still a long way to go. The most popular questions from our Discussion Day and the betting experts’ responses are below.

How important is your staking method?

When you bet for a living, it isn’t about always making money. One of the keys to success is to limit your losses when you don’t win. Even the most profitable bettors will place losing bets - the trick is to use the right staking method that will manage your money in the most efficient way possible.

You could create the perfect model with better results than anyone else but if you don’t use the right staking method, you will eliminate any edge you have. There are countless staking methods that most bettors will be aware of - our Staking: One method to improve your betting article tests several of these and answers the question; which staking method is best?

Understanding the value of information

Bookmakers will effectively buy information from bettors by offering odds and then make adjustments to the market depending on how valuable that information is. Professional bettors can make money by predicting the outcome of a match based on skill, but they can also do it by using information no one else has - the most successful bettors will obviously use a combination of both.

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Whether it is a soccer player being injured, an NFL quarterback being suspended for disciplinary reasons or a sudden change in weather or playing conditions, knowing about something before anyone else and acting on it will affect how profitable a bet can be.

It's not just about predicting skill

While any edge you have requires the right staking method to maximise its profitability, it is pointless having the right staking method if you can’t predict the outcome of an event and calculate whether your potential bet has positive expected value.

Instead of trying to bet on anything and everything, you will be better off focussing your attention on one particular sport. Sometimes niche markets like corners betting offer better value because there is a lack of bookmaker knowledge, but there is still money to be made with an NFL betting strategy or by betting on the Over/Under market in soccer.

What sport should you bet on?

As mentioned above, if you want to become a professional bettor, you need to find an edge over the bookmaker in any sport or market you can. However, some sports might be easier than others when it comes to forging a career in betting.

Pinnacle’s Betting Resources can help you learn how to bet on baseball or teach you about the basic basketball bet types. It also explains how external factors can be more influential in some sports compared to others - Golf betting, for example, can be heavily influenced by luck.

How do you measure betting success?

The most efficient way to measure if your betting exploits can be deemed a success is to compare them against the closing line (the most adjusted, and therefore accurate odds available before an event takes place).

Testing the results of your strategy against a bookmaker’s closing line over a long period of time eliminates the influence luck could have. Similar to testing the credibility of a tipster, analysing your own results is essential if you want to become a professional bettor.

How to find the right bookmaker

Becoming an expert in a particular sport, developing a successful strategy and ensuring you use the correct staking method to maximise returns whilst limiting your potential risk might be the hard part, but finding the right bookmaker can be just as difficult.

If you want to make enough money from betting to earn a living, you need to use a bookmaker that consistently offers the best odds. Being able to bet as much as you want is also important, so using a bookmaker that offers the highest limits online makes sense. Finally, you need to bet somewhere that welcomes winners and won’t restrict or ban anyone that makes money from betting.

Find out how to calculate betting margins so you can work out how Pinnacle compares to other bookmakers.

In addition to the advice above about how to become a professional bettor, there are some basic rules that all bettors should try and stick to. Don’t let emotion get in the way of betting, don’t get fooled by randomness or controlled by optimism bias. Finally, as world famous bettor Lewis Deyong explained in his interview with Pinnacle; 'Never bet money you can’t afford to lose.'

Ready to test the waters as a professional bettor? Bet with the best odds online at Pinnacle. Need more advice? Follow us on Twitter for unique betting insight.