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Legends of the Punt
Bill Benter: The most successful racing punter of all time?
Bill Benter: The most successful racing punter of all time?
Rowan |  May 7, 2023
It’s suggested by some that Bill Benter is the world’s most successful gambler. While estimates of his worth are largely speculation, they range from several hundred million to more than $1 billion. And he won all of it on the punt. So how on earth did he achieve this? And is this sort of success possible for any punter, given the right opportunities? Let’s track his journey.
1. Benter’s beginnings
Bill Benter grew up in Pittsburgh, Pennsylvania and always had a mathematical mind.

He studied physics at university, but his destiny changed when, by a quirk of fate, he came across a copy of the famous gambling bible ‘Beat the Dealer‘, by Edward Thorp. Thorp is known to many as “The Godfather of Card Counting”, and his methods spoke directly to Thorp’s mathematical mind. Benter had an aptitude for the probabilities involved, so got to work memorising every detail of Thorp’s book. Then it was time to put it into action.

2. Bill Benter takes on Las Vegas
Bill Benter was keen to use his natural mathematic prowess and his newly-learned blackjack and card-counting skills to make a profit. Predictably, he chose Las Vegas and its myriad of casinos as target.

Thorp’s approach, as adopted by Benter, is reasonably common knowledge these days. Players gain an advantage by counting cards – keeping track of the number of high and low cards that come of the deck, and therefore knowing the value of the cards that are left in the dealer’s deck. From there, it’s a matter of waiting for the right time to strike. When there are a high ratio of high-value cards (such as 10s and aces) left in the deck, the chances of drawing a desired card fall into the player’s favour. If the player then sticks to the optimal strategy for blackjack – known as basic strategy – the odds are tipped in their favour.

It’s not a simple process, requiring the player to memorise large amounts of information and then use it to make split-second decisions as cards are dealt. But for those who can master it and play accurately for long enough, the odds say they’ll end up in front.

Benter was one who was able to master card counting. While it’s impossible to know just how much he won, Benter spent seven years in Vegas playing full-time.

As knowledge of card counting grew, the exponents of it became public enemy #1 for casinos! These players were winners, and winners are not welcome in casinos. The houses banned card counting and upped their efforts to quickly identify those doing it – including employing card counters as lookouts. Inevitably, Benter was caught up in the crackdown and was banned by all Vegas casinos.

3 Benter beats roulette?
This part of Benter’s tale is very light on evidence, but it’s fun speculation all the same. There are stories told that during his time in Las Vegas, Benter developed a system that was actually able to beat the odds at roulette. The system – that he supposedly created in his spare time in between playing blackjack – was said to be able to calculate the speed at which the roulette ball was travelling immediately after release. If a player could memorise the equation to measure the ball’s speed, note the ball’s entry point and instantly calculate the formula in their head, they would supposedly be able to determine which quadrant of the wheel it would end up in.

Again, it’s never been confirmed. But it’s some story!

4 Bill Benter meets Alan Woods
Around the time they’d both been banned from casinos, Benter met a fellow blackjack professional, Alan Woods. Woods had studied to be an actuary but was an all-round gambler and a horse racing expert. The two joined forces in 1984 and set about turning their success in Vegas into a consistent edge at the racetracks of Hong Kong. Hong Kong is one of the world’s biggest horse racing markets. Crucially, there are plenty of casual punters more focused on luck than worrying about winning long-term.

Benter, Woods and a third member, Wally Sommons, worked together on a horse racing system that backed favourites. They quickly discovered that if they bet on overlays they had a decent edge. However, it took some time before their efforts were rewarded.

Over the course of two years, the team managed to give away most of their $150,000 starting bankroll. But after another couple of cash injections, they managed to get their system working. They made $100,000 profit in their third year.

5 Bill Benter goes solo
In 1987 the team split up following disputes over money. Benter was determined to continue on his own, taking the early model and building it into something more powerful. The focus of Benter’s model was to determine the various factors in racing and then weigh them accordingly.

The tool Benter used for this was known as multinomial logit regression. This tests factors to determine their significance as to the outcome of a race – more specifically, if it leads to the horse winning. The multinomial logit regression model then calculates the weighting of the factors.

In the early days, Bill Benter started out with only 16 form factors to determine the outcome of a race. Many of the factors were calculated manually and databases were created from scratch. Over time the number of factors grew more than 100 as Benter incorporated not only statistics but also video analysis and subjective form factors. Benter’s model allows him to determine the ‘true odds’ of every runner in a race and only bet on overlays. He also uses the same mathematical techniques to bet on the huge exotic pools in Hong Kong.

Since 1987 Benter and his team have won incredible amounts in Hong Kong. These days he also spends his time lecturing on mathematics and statistics at Harvard, Hong Kong and Southampton. Much of his time is also dedicated to philanthropy, through the Benter Foundation, and he also has a considerable presence in politics and makes regular political donations.

It’s an amazing rise from humble beginnings.
Other Posts
Billy Walters: Rags to riches
Rowan |  Dec 1, 2022
Billy Walters might just go down in history as the most infamous name in high stakes gambling.
Walters grew up in a small town called Munfordville in Kentucky. His family didn’t have much: not even indoor plumbing. They were, however, avid gamblers. Walters’ father was a keen poker player and his uncle was actually a professional gambler for a time. These figures in childhood would have a profound effect on Billy Walters. His keen interest in the punt developed early.

At the age of nine, Walters took the money he earned on a paper round and wagered it on the World Series. That bet would be the beginning of one of the great gambling careers.

As he got a little older, Walters raised what money he could by selling second-hand cars, and at the same time set about becoming a bookmaker. This was, of course, illegal in his native Kentucky. He was prosecuted and fined $1,000.

Walters didn’t need any further incentive to move. He headed straight to the gambling mecca of America: Las Vegas

Billy Walters: Legendary Sports Bettor
Walters made his name as a sports bettor, but in the early days also played poker and other table games. He was somewhat successful in poker tournaments and won at roulette. The story regarding his roulette success goes that he gained an edge by identifying that older roulette wheels wore in different places, making them predictable and ultimately profitable.

In Vegas, Walters connected with two others to form one of the first computer-based betting syndicates. Walters, Michael Kent and Dr Ivan Mindlin exploited early data techniques to build computer algorithms for sports betting. Walters’ role was largely to get the money on, exploiting the weakest lines the group had identified placing the biggest wagers possible. The size of the bets skyrocketed and ultimately, so did the profits.

Operating in the pre-internet era, Walters and his associates were ahead of their time. One of their famous ploys was dispatching runners to the airport to grab interstate newspapers immediately, getting a jump on any sports news and using it to their advantage. Before long the runners were also placing bets on behalf of Walters, with sportsbooks unwilling to take him on.

Property Deals
As Walters’ wealth grew, so did his search for bigger edges – both in and beyond gambling.

Walters used his wealth to expand into property and the stock market. An avid golfer who plays off scratch, in 1996 he won a contract to develop a Las Vegas golf course. It was Walters’ idea to purchase the land outright, and he negotiated an extremely good price with the city to do so. Real estate values in Vegas would soon take off, with Walters and his partners gaining planning permission to redevelop the land into residential property. This would prove Walters’ biggest payday, pushing his personal wealth well beyond $100 million.

The stock market & coming undone
On top of decades of success in sports betting, Walters had long played the stock market successfully. But in 2017, Billy Walters’ luck ran out.

Walters was receiving stocks tips from Thomas Davis, chairman of Dean Foods. Davis reportedly had a gambling habit and fed tips to his friend Walters. Investigators would ultimately charge Walters with insider trading. He was convicted and sentenced to five years in prison. In 2020 Walters, 73, was permitted to serve the remainder of his sentence in his California home… where a cable television subscription and phone access will be welcome luxuries!

Insights from Billy Walters
Billy Walters may live a somewhat more low-key existence now, but the proof of Walters’ success is clear: hundreds of millions in profit over decades, and an empire that includes mansions, golf courses, hotels, property developments, car dealerships, a private jet and various other business interests.

So what are the lessons we can learn?

Information gives you an edge
Billy Walters surrounded himself with sharp minds of very different backgrounds whose only contact with the syndicate was a direct line to Billy. They didn’t know or have anything to do with each other. Walters employed an array of experts in the roles of consultants, statisticians, mathematicians and computer programmers to help him compile, analyse and ultimately profit from huge amounts of information.

Whether it’s business or gambling… value is everything
“If you value something at ten, then you’re a buyer at eight and a seller at 12.”

Walters wasn’t emotionally attached to teams or players. His concept of value is very different to how many punters operate, which is to back a favourite team or horse without seriously analysing whether the odds available represent good value.

The bigger the value, the bigger the bet

The Walters team produced their own lines and only bet when they are different to the market. The bigger the difference between their line and the market odds, the more they bet.

He had incredible confidence in his own numbers and looked to exploit his advantage the most when that edge is the biggest. That’s not to say that it’s all about making one big bet – Walters spreads out his bankroll across many opportunities where he has a positive expectation.

… but we’re not talking huge margins
Simply tossing a coin will get you a 50% strike-rate.

But to be profitable, betting at the standard odds of $1.90 requires a strike-rate of 52.4% or more.

For all of his work and success, Walters winning strike-rate is estimated to be ‘just’ 57%. But the sheer volume of his bets and the ability to optimise his bankroll management has enabled him to amass hundreds of millions in profits.

Don’t expect instant success
“I know what every sucker thinks, because I used to be one. I can assure you that every successful gambler I know has been through some monumental failures on his way to getting there.”

Walters went broke many times early on and described his younger self as a compulsive loser and gambling addict.

Early failures are a very common experience amongst gamblers who ultimately become very successful. Many punting lessons are learned the hard way.

Don’t become a dinosaur
“I probably had to re-invent myself 25 times in the last 20 years. If I hadn’t re-invented myself, I would have been out of business. That goes for anyone in any business. There’s going to be constant change of any industry you’re in and if you don’t change with it and you don’t change ahead of it, you become like a dinosaur. You become extinct.”

“The game of handicapping sports is really the same game as it was 40 or 50 years ago. It’s much more competitive now, and the numbers are much better than they were in the 80s, but it’s still the same game. It still comes down to evaluating information.”

The edge that came from reading all the small-town newspapers disappeared as soon as the internet became widely available. Edges disappear over time – sometimes gradually and other times quite quickly.
Walters repeatedly adapted his approach to stay ahead of the game, whilst understanding that the fundamentals of gambling success remain unchanged.

Execution is as important as edge
“The computer whiz kids who are involved in sports today don’t have a clue, I mean a clue about how to bet their money. They don’t have a feel at all for which way the line is going to move. There is a big difference in knowing how to bet and when to bet your money in sports. It is almost as important as handicapping.”

Don’t be in denial
“A lot of people have a difficult time stepping back and doing a re-valuation and deciding ‘I was wrong’. A lot of people want to continue on in denial until they’re completely broke.”

Long-term winners DO exist
Walters amazing ability to beat liquid markets over such a long period is living proof that success is possible.
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David Walsh: 8 lessons on punting and life from the billion-dollar bettor
David Duffield |  Jan 28, 2025
David Walsh and Zeljko Ranogajec rose from humble Hobart university students to become two of the most successful professional gamblers in history. Their betting syndicate turns over literally billions of dollars each year and is recognised as one of the world’s biggest gambling operations.
Both David Walsh and Zeljko Ranogajec are private individuals who rarely – if ever – speak publicly about their gambling operations. But in 2018 when Walsh granted a wide-ranging interview to The Good Life podcast, he covered many fascinating gambling topics.

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We’ve summarised the highlights from this rare public conversation with David Walsh, so you can learn from one of the best ever!

8 lessons from David Walsh
  1. The wisdom of crowds is very real
  2. Recent trends are over-bet
  3. Longshots are poor value
  4. Weight is overrated
  5. It’s not about picking winners
  6. You must avoid ruin
  7. Pokies are poison
  8. Luck plays an enormous role for the ultra-successful

1. The wisdom of crowds is very real
“My experience of gambling taught me to understand that the wealth and prestige that I grew to possess had very little to do with my talent. I didn’t gain wisdom by standing on the shoulders of giants. I gained wisdom by surfing the crowd,” says David Walsh.

“We’ve done a lot of analysis on horse racing over the last 30 years. It took me years before I was able to generate a model that was more accurate than the public. Turns out it doesn’t matter how much analysis you do, how sophisticated you are, how much you know about regression and logistic regression… you end up with a model that is inferior to the public unless you include the public market as a factor in your model. So, what you end up with if you’re actually going to win is a perturbation model that assumes the public is right but also finds the biases that they introduce. Things that in the psychology literature are called cognitive biases.”

2. Recent trends are over-bet
“The hot hand bias is an example. There’s a belief in basketball that someone who has had a great three-point percentage throughout the game is more likely to make a three-pointer in the last quarter than he was before. When, in fact, their lifetime average is the better predictor of the next outcome,” says David Walsh.

“Hot hand bias is foraging behaviour. It was once useful, this cognitive bias, but now in certain applications, it leads to misadventure.

“We get the odds mostly right but when there’s been a particular sequence, like a jockey has won a bunch of races, we might think they’re more likely to win the next race. We overweight trends.”

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Think. Is this a bet you really want to have?
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3. Longshots are poor value
“If you back a favourite in a horse race you might lose 2 or 3%. If you back a longshot, you might lose 40%. That’s preferred for two reasons,” says David Walsh

“The first is for boasting rights because if you happen to get a winner it’s very useful and I believe that plays a big part, especially with men who exert this bias more than women.

“The second is non-linear utility. 1x $100 might be worth a lot more to you than 200x $1. Because $1 has no apparent purchasing value to you, whereas $100 does.”

4. Weight is overrated
“Punters tend to overweight the importance of the weight the horse is carrying. Don Scott was a gambling guru who published his system based around weight and a lot of people incorporated this ideal into their behaviour. He was wrong about it as a feature – it was never as relevant as he thought it was. But once you misdirect the wisdom of the crowd, they’re all over-playing this. As far as I know, this feature doesn’t exist in many markets,” says David Walsh.

“You get huge negative coefficients on weight if you include the public. You get huge positive coefficients on weight if you don’t include the public. Weight is relevant to the outcome, but it is over-discounted by the weight of numbers.”

5. It’s not about picking winners
You don’t need to forecast the outcome. A lot of people aren’t aware of this. What you need to do is simply get odds that are better than the public odds. I use a die analogy quite often…it doesn’t matter what number you bet on, if you can get 10/1 and it’s a fair die, you’ll make money. If you get 4/1 you won’t make money. Every economist knows that, but it isn’t universally known, and it probably should be,” says David Walsh.

6. You must avoid ruin
“The first thing that successful investors do that is a discriminating factor based on being different from inputs (and I didn’t do this) is survival,” says David Walsh.

“When you have lost half your capital you’ve got to bet half the size. Because the biggest thing that can happen to you is destruction. The first thing you’ve got to avoid is ruin. And that applies to anything you do.”

7. Pokies are poison
“If you bet on the horse races there’s about 1 chance in 5000 it’ll destroy your life because you’ll become addicted,” says David Walsh.

“But if the first time you bet is on a poker machine there’s about a 5% chance that it’ll destroy your life.

“If you’ve never placed a bet, the best decision you can make is to never place a bet. If you’re ever going to place a bet, don’t do it on a poker machine because the ‘addiction-by-design’ clever bastards built them.”

8. Luck plays an enormous role
“Success is only slightly correlated with talent,” says David Walsh.

“When we see a magazine interview of an ultra-successful Bill Gates-type they only look at the output cohort. They don’t look at the input cohort. I always use tennis as an example…there is no point in interviewing Roger Federer because all of the things he has done to make him good, the people who didn’t become good also did. It might seem incredible but most of his edge was a lucky retrospective outcome. He was slightly better than everyone else and there’s a feedback loop and he got better and better.”

“There were a lot of people including me who made really bad business decisions early on and got lucky. I over-estimated my edge and there was about a 20% chance of succeeding with my horse racing gambling. That’s not a good position to be in.

“There were a lot of other people like me that were just as talented at gambling and figured out the same strategies as me and made the same mistakes as me…but they got wiped out and I didn’t.

“And then of course once I’m in the market and successful, people like me make the characteristics of the market more untenable and more deceptive. So that the new players think they’ve got an edge but are less likely to have an edge. And indeed, they’re less likely to bet big with the edge that they have. So, they’re more likely to blow up.”

Listen to the full podcast with David Walsh here

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The Unlikely Partnership That Built a Billion-Dollar Betting Syndicate
Rowan |  Jan 29, 2025
Zeljko Ranogajec & David Walsh
Few people outside the gambling world know the name Zeljko Ranogajec. In stark contrast, his best friend and business partner David Walsh has gained notoriety for his efforts away from the casino and racetrack. Together they have grown one of the most powerful gambling operations the world has ever seen, although little is known about the inner workings.

Having met in Tasmania, Walsh and Zeljko (everyone calls him Zeljko) began their gambling journey at Wrest Point Casino through a group of like-minded friends, intent on beating the blackjack tables. Walsh, who was borderline Aspergers, has an incredible mind for mathematics and was a great fit with the charismatic and business-savvy Zeljko.

Before starting their punting journey, Walsh gained a degree in mathematics and then worked at the ATO. Zjelko studied to be a lawyer and was working at the casino. As their skills grew, they moved to Sydney to pursue more opportunities. However, casinos Australia-wide quickly caught on and refused to take their action.

How it started

Walsh and Zeljko were beating the casinos in the early days by counting cards. They gained an edge by tracking the ratio of high and low cards as more and more hands were played in each shoe. In Blackjack, tens and aces have the most value. If a shoe is dealt out and a lot of smaller cards (2s to 6s) have been seen, that means there is a higher probability of landing a blackjack, which pays out better odds. Card counters become advantage players and incur the wrath of casinos.

As their skills at the tables developed the duo also got involved in working in a blackjack team and pooling their bankrolls in a betting syndicate. By working as a team, they could stay under the radar for longer and turn over more money. However, their betting eventually got to the point that they were no longer welcome at Australian casinos, so their attention turned to other forms of advantage play.

Horse Racing

After building a bankroll well into the millions, Zeljko and Walsh turned their attention to horse racing. They focused on all manner of ways to build systems with an edge. Their focus has always been on generating rebates and turning over huge amounts of money on the Australian and global totes.

Many totes cater to large punters and betting syndicates by offering a rebate on losing bets. These rebates range from 2-10% and are enough to turn a mildly unprofitable betting strategy, into a winning one. The systems they deployed involved both statistics and video form analysis and are reported to account for 6-8% of the TABs revenues.

One of the major focuses of the betting operations was the betting exchange Betfair. The team not only placed outright bets on a wide range of sporting events but also developed systematic strategies that capitalised on market mispricing in almost every event that was available to be bet on. Specifically, they looked for markets that were framed below 100%, based on the available odds and they could quickly take up those opportunities.

As operations grew, so did the scope of what was now a gambling business. To gain better and more accurate data that wasn’t widely available, Zjelko outsourced many operations to contractors and at the same time set up a multi-million-dollar office in Pyrmont. They reportedly use a network of spotters, analysts and bettors to both get bets on and gain the most accurate data available.

Keno

It was reported that in 1994, Zeljko started visiting the North Ryde RSL Club in New South Wales, trying to take down a $7.5 million jackpot. He eventually won the jackpot, but not before he spent a decent portion more than that on wages. It was said that he managed to make a profit thanks to several smaller prizes along the way.

MONA

While Zeljko was heavily focused on building his gambling empire into a billion-dollar business, Walsh was focused on another great passion of his – art. Over the years Walsh had obtained a wide-ranging art collection and in 2011 officially opened a museum that featured much of it. The Museum of Old and New Art (MONA) is based in Hobart and is the largest privately owned museum in Australia.

The museum boasts over 400 artistic works from Walsh’s private collection and is now one of the main attractions in Tasmania. To fund the museums and its operations, Walsh took an $80 million dollar loan from Ranogajec.

ATO Troubles

For nearly 30 years the Australian Tax Office (ATO) has been looking into the gambling operations of Zeljko and Walsh. In Australia, gambling is considered to be a hobby and as such is free from taxation. Some of the early investigations by the ATO confirmed that, but in more recent years the sheer size of their operations and the fact that it operates like a business has opened them up to the tax man.

It was reported that the ATO was seeking to reclaim more than $900 million from the betting operation in back taxes. Zeljko and Walsh were prepared to pay in the order of $50 million. At the time Walsh suggested to the media that he would be forced to shut down MONA if the ATO kept on pursuing them.

MONA had become one of the largest tourist attractions in Tasmania and became a key bargaining chip in negotiations. Ultimately Zeljko and Walsh settled with the ATO for an undisclosed sum. Even Walsh appreciated the irony as he had started his career many years earlier working for the ATO, who ultimately nearly ended it.

Given the highly secretive nature of their betting operations, more is speculated about Zeljko and Walsh than is known. Estimates of their net worth is just a guess, and employees of seven years like former Champion Bets analysts Aaron Barby never even crossed paths with Zeljko.

What is known is that together they formed one of the most innovative and impressive gambling operations the world has ever seen. For many years they were able to do it under the radar, until ultimately, they become so big and so successful that they could no longer avoid the spotlight.

Lessons learned

David Walsh shared some of his best betting advice on a podcast interview:
  1. The wisdom of crowds is very real
  2. Recent trends are over-bet
  3. Longshots are poor value
  4. Weight is overrated
  5. It’s not about picking winners
  6. You must avoid ruin
  7. Pokies are poison
  8. Luck plays an enormous role for the ultra-successful

>>> David Walsh's eight betting tips is a great read.

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