The Most Successful Gamblers in the Last 50 Years

Many folks think of gambling as being purely a matter of luck. However, consistent winners over the years prove that some forms of the pastime involve a lot of skill. Sure, you don’t often see the same names winning national lotteries repeatedly but, in other games of chance, the best players do indeed rise to the top more often than not. 

In this article, we look at five of the most successful gamblers from the last half a century. Their skill allowed them to overcome the element of luck in their respective betting endeavours. So, here they are!  

Phil Ivey

Hall of Famer Phil Ivey is an absolute legend in the world of poker. The 43-year-old California native has won an impressive 10 World Series of Poker bracelets from 31 final table appearances. Three of those came from the 2002 event alone. Yet, despite being known as the Tiger Woods of poker, he’s, unfortunately, never actually taken down the WSOP main event – no doubt a serious bone of contention for Ivey!

Ivey’s success isn’t limited to collecting World Series bracelets though. He’s also the holder of one World Poker Tour title, having made the final table nine times in total. Overall, he’s taken more than $26 million in tournament winnings but tournament poker is by no means the only string to Ivey’s bow. A prolific online and live cash game player too, it’s practically impossible to tally the millions he’s made away from tournament tables. 

Chris Moneymaker

The appropriately-named Chris Moneymaker might not be quite in Ivey’s league, yet he’s still a legend in his own right. Moneymaker won the 2003 World Series of Poker, having qualified for the main event through an online satellite game. He effectively turned $86 into $2.5 million. The story inspired millions of people, effectively kickstarting a boom in online poker. 

The Georgia-born player’s success wasn’t limited to one epic winner though. He’s also taken down prizes at several other notable tournaments. His second place at the 2004 Shooting Stars event on the World Poker Tour earned him $200,000 and two decent finishes at the 2008 World Championship of Online Poker netted a further $167,000. Moneymaker also finished well in tournaments in 2009 and 2011, taking his total live tournament winnings over $3.67 million. 

His biggest contribution to poker, however, was to show that it was possible to beat household names like Phil Ivey and Doyle Brunson at their own game. For that, he was inducted into the Poker Hall of Fame in 2019. 

MIT Blackjack Team

It’s easy to understand the element of skill in a game like poker. Players face off against one another and their actions influence how the game unfolds. Yet, skilled players can do very well in other card games too. Blackjack is one such example. However, consistent wins require outsmarting the casino itself. That’s where card counting comes in! 

Card counting is a system that attempts to track the probability of favourable cards landing for players at the blackjack table. Essentially, it’s a form of advantage play. Card counters will remember the cards that have already been dealt. They wait for opportunities to increase the size of their bet to take advantage of the odds being in their favour. 

Edward Thorp, a Chicago-born maths professor, effectively invented card counting and wrote the 1966 book Beat the Dealer. Although Thorp, rightly, became a legend in the gambling community, it was the MIT Blackjack Team that took his ideas and ran with them. 

The team was comprised of a group of present and former Massachusetts Institute of Technology students. They operated various highly successful card counting rings from 1979 until the early 21^st century. It’s difficult to quantify how much the team actually made using their card counting techniques. However, they were profitable enough to warrant a movie in their honour. The 2008 motion picture 21 pays homage to what is surely the most successful blackjack group in history. 

Zeljko Ranogajec

Tasmanian businessman and gambling legend Zelijko Ranogajec is easily one of the most prolific gamblers of recent years. In fact, the Australian Daily Telegraph claims he’s bet around $1 billion in a single year at venues around the world. The man actually denies being the world’s biggest bettor but many disagree. 

Ranogajec found early success at the Wrest Point Casino playing blackjack. The gifted mathematician understood that keeping track of the deck could give him an edge to exploit. His skills encouraged him to strong out of university in the mid-1980s. Eventually, the casino staff wised up to his card counting and banned him from playing.

The Aussie’s real passion, however, is horse racing. He’s known for placing massive bets and deploying advanced systems that take advantage of mug punters. In fact, his betting operation is believed to employ more than 100 people who analyse form and spot profitable propositions. 

However, it’s not exactly clear just how much Ranogajec has taken from his escapades at the blackjack felt or track. Much of his life is shrouded in mystery. Reports suggest that he goes by an alter ego – John Wilson – to fly under the radar. One of those working for his betting operation even told a journalist: 

“If he knew I was talking to you about him, he’d never talk to me again.”

Gambling has changed with the emergence of online casinos. There are now over 5000 online casinos offering casino games across the world. It interesting to note that the most successful gamblers cannot replicate their epic wins online. This is due to restrictions on wagering amounts and the simple fact that many of these online casinos cannot pay out huge wins. These sites are really better for casual gamblers.

Alan Woods

Another Aussie with a particular penchant for a punt is Alan Woods. Woods also got his start counting cards at the blackjack table. Introduced to the system by a group of bridge players, the businessman and mathematician racked up big wins in Hobart and Las Vegas before retiring from blackjack to focus on horse racing in Hong Kong. 

Together with two associates, Woods developed a computerised model to pick winners. The system considered form, previous winners, track conditions, and other factors. It was incredibly profitable. In fact, it’s widely regarded as being one of the most successful ever. 

After parting ways with the original syndicate, Woods actually teamed up with Zeljko Ranogajec. The pair continued to reap the rewards of their understanding of racing at the tracks in Manila. Woods passed away in 2008. However, his legacy lives on. He’s believed to have generated a fortune of more than AU$670 million!

Just a Handful of Greats from the Last Half Century! 

Unfortunately, this article isn’t long enough to really delve deeply into the many legends of gambling from the last 50 years. Notable omissions from the casino floor include Stu “One of a Kind” Ungar, Doyle “Texas Dolly” Brunson, the Finnish phenom Patrick Antonius, Don Johnson (a hugely successful blackjack player that didn’t count cards), Phil “the Poker Brat” Hellmuth, or Daniel “Kid Poker” Negreanu. Then there’s the legends of betting on horse racing. Amongst them we could have included the likes of Kerry Packer, David Walsh (best friend of Ranogajec), and Harry Findlay. Each could easily be the subject of their own dedicated article!