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Famous Australian Gamblers

13 July 2023 - 3 min read

Our list of five of the most famous gamblers includes names you will be familiar with, including an immigrant’s son, a bullish business tycoon, a whizz-kid programmer and a real estate hotshot who lost over a billion dollars in thirteen months. Intrigued? Read on to find out more about this (in)famous five!

Table of Contents


Harry Kakavas  - Australia’s Biggest Loser?

Every member of this esteemed group of famous Australian gamblers has at some stage had big losses to go along with their wins. None, however, can match the quite extraordinary losses of Harry Kakavas who reportedly lost $1.5 billion in a single, solitary year!


Before experiencing outrageous losses in the casino, Kakavas was an extremely successful businessman. He had an undeniable gift for sales, and he converted that ability into becoming one of the most notable real-estate salesmen in Gold Coast making millions through the late nineties and early noughties.


His gambling would soon lead his life in a different direction. Soon, his gambling losses mounted up and he lost a reported $1.5 billion in just thirteen months, from June 2005 to July 2006. Had he accepted the losses and carried on with his life his losses may not have been so public. Instead, everything was disclosed as he sued the Crown Royal casino claiming they took advantage of his addiction to gambling. Unfortunately for Kakavas, he could not shake the losing habit as both the High and Supreme Courts ruled in favour of the Crown Royal.


David Walsh –  Gambling With Syndicates

Tasmania-born David Walsh is one of the most famous gamblers Australia has ever produced. He and fellow Tasmanian Zeljko Ranogajec gained notoriety in gambling circles when they formed The Bank Roll, a gambling syndicate which used quantitative research to beat the bookies across the world.


The Bank Roll developed their own statistical models to hunt down and take advantage of what they considered to be errors in pricing by bookies at home and abroad. The result? Almost three decades of success and hundreds of millions of dollars won.


While his gambling success brought him fame, Walsh’s legacy is likely to be in the world of art. Using his winnings from gambling, Walsh built the $75 million Museum of New and Old Art (MONA) in his hometown of Hobart. The museum, partially funded by an extraordinary $17 million win at the 2009 Melbourne Cup, has become one of Tasmania’s biggest attractions and ensures that Walsh’s fame extends further than the racetrack.


Zeljko “The Joker” Ranogajec – Billion Dollar Gambler

The fiercely private Zeljko Ranogajec is possibly the most famous gambler in the world. As the co-founder of the betting syndicate The Bank Roll, Ranagajec and his colleagues found both success and a place on the backlist of every casino in Las Vegas and Australia thanks to their incredibly successful blackjack strategy. For many gamblers, being blacklisted by so many casinos may be the end of the road, but not for Ranogajec and his merry band.


Instead, following their swift exit from Las Vegas, Ranogajec turned his attention to the keno tickets of Australia.


He and his colleagues bet millions upon millions of dollars on keno games, eventually winning a record $7.5 million in 1994. These winnings were reinvested in a series of subsequent keno draws, with around 90% of all available tickets purchased by the syndicate. The investment proved to be sound as some experts believe that the group took home jackpots in 40 of Australia’s 44 jackpot draws.


While the group was successful in keno and blackjack, this success was dwarfed by the triumphs they enjoyed on the racetrack. With a strategy in hand, Ranogajec’s group are thought to regularly generate a turnover of over $1 billion on horse racing each year. All of this has contributed to The Joker having an estimated net worth in 2022 of over $610 million and a reputation of being one of the world’s greatest gamblers.


Alan Woods – Gambler Programmed to Win


Whilst the other members of this list have had been prominent gamblers, none have revolutionised the industry like Alan Woods. Born in New South Wales, Woods was one of the first punters to leverage technology in sports betting.


In the 1970’s Woods was introduced to card-counting by a friend, and he quickly proved quite adept! Soon, he left Australia to implement his strategy in the casinos of Europe, Asia and Las Vegas. As his success grew, so too did his fame amongst casino bosses and before long not even his extravagant disguises could help avoid being removed form any casino he visited.


In actual fact, it would prove fortunate that Woods was no longer able to visit casinos as it focused his attention in another direction, a direction that would see him become wealthy beyond belief. Teaming up with fellow gambling legend Bill Benter, Woods built a a computer programme which used data to predict the outcome of horse races.


After a rocky start, he made $100,000 in his third year and that number only continued to grow as the years went by. By the time of his death in 2008, Woods’ fortune had swelled to over $680 million, mostly thanks to his revolutionary computer programme.


Kerry Packer – Australia’s Greatest Gambler

How to describe Kerry Packer? Billionaire business tycoon, media mogul and cricket fanatic are just a few ways to describe the famously bullish entrepreneur. Packer was all of these things, but he was also a legend in the gambling world for his extreme play and lavish tips.

Packer’s business career is the stuff of legend, as the billionaire racked up win and after win in the media world. The story of him selling Nine Network to Alan Bond for $1 billion only to buy it back for $200 million two years later has become entrenched in business folklore. Whilst he did not have any $800 million wins on the casino floor, his prolific wagering was known to be so extreme that it could even affect a casinos stock price!

Being a billionaire does not increase your chances of winning, but it does afford you the opportunity to make bets that result in wins and losses beyond most people’s comprehension. One such loss totalled over $15 million when Packer perhaps overextended himself by playing four simultaneous games of roulette. In another famous tale, he rented a private room in The Ritz in London only to find himself suddenly down more than $19 million in one night! This loss went down in history as the biggest the country had ever seen.

It was not all doom and gloom for Packer however, as he was also one of the biggest winners of all time on the blackjack table. In the MGM Grand in Las Vegas, Packer made the decision to play eight separate hands of blackjack at the same time. Packer was betting $250,000 on each hand, and just kept winning, and winning and winning!

To the casino boss’s relief, he finally stopped after playing for 40 minutes, but that was only after he had racked up over $20 million in winnings. You may think that no one in that casino could possibly be happier than Packer after that effort, but you would be wrong! Packer’s tips were as legendary as his gambling and the staff at the MGM on that fateful night took home a share of his $1 million tip!

Although Kerry Packer died in 2008, his place in gambling history is assured forever. Even today his name  is heard on casino floors across the world and stories are still shared of this casino legend whose exploits have become almost mythical!