High-Stakes Titans: Chronicles of the World’s Richest Gamblers in 2024

Gambling is a divisive topic. Moralists consider it sinful, while others deem it an enjoyable hobby they can profit from. The financial implications behind gambling make it such a compelling activity.

Worldwide, many high-profile individuals have established themselves as the kingpins of gambling, either from big casino wins or developing innovative ways to dominate the betting scene.

This article discusses the richest gamblers in the world, exploring vital information and key betting moments to see how they’ve wagered their way to the gambling summit.

Highlights of the Article

• Kerry Packer faced a setback, enduring a staggering loss of nearly $28 million while gambling at London Casinos, marking the most extensive recorded loss in British history.
• Bill Benter won the 2001 Hong Kong Jockey Club’s Triple Trio, which was estimated at $118 million.
• Edward O. Thorp’s book on Blackjack became an instant success, selling over 700,000 copies and earning a place on the New York Times bestseller list. 
• Billy Walters, a serial sports bettor, made history in 2010 by winning $3.5 million with a strategic bet on the Super Bowl.
• In 2007, Terrence Watanabe experienced a significant downturn, losing $127 million in Las Vegas after placing bets totaling $835 million, marking the city’s most substantial losing streak.
• Zeljko Ranogajec is credited with achieving the highest Keno win on record, totaling approximately $7.5 million at a New South Wales casino.
• In February 2014, Phil Ivey claimed a cash prize of AU$ 4,000,000 after emerging victorious in the 2014 Aussie Millions LK Boutique $250,000 Challenge.
• Sam Farha’s most significant success occurred on May 23, 2003, when he earned $1,300,000 for securing the 2nd position in the 34th World Series of Poker (WSOP) 2003.

The Top 14 Richest Pro Gamblers in the World

1. Kerry Packer – Las Vegas’ Splashiest Player
2. Tony Bloom – Richest Football Punter In The World
3. Bill Benter – The Man Who Used Math To Beat The Bookies
4. Edward Thorp – The Godfather of Card Counting
5. Andrew Black – The Programmer Who Predicted Horse Race Results
6. Alan Woods – The Best Horse Handicapper of All Time
7. Zeljko Ranogajec – Biggest Advantage Bettor in Australian History
8. Billy Walters – The Most Successful Sports Bettor Vegas Has Seen
9. David Walsh – The Eccentric Modern Gambler-Art Connoisseur
10. Terrance Watanabe – The Biggest Whale in Gambling
11. Dan Bilzerian – The Controversial “King of IG”
12. Phil Ivey – The GOAT of Poker
13. Sam Farha – The Old School Gamber
14. Mikki Mase – The Self-Proclaimed Degenerate Gambler

Many people gamble for fun. Still, some people make a living by gambling professionally, either by winning in tournaments and sportsbooks or by using their fame from betting as leverage.

Helpful Articles

Individuals aspiring to be on lists like this and surpass the personalities below must learn the various factors behind mastering the art of gambling.

 

Understanding aspects such as RTPs, payout rates, and casino games offering the best winning odds is essential for bettors who dream of hitting the jackpot.

The world’s richest professional gamblers amass huge fortunes by harnessing their winning odds at casinos, using cunning strategies, relying on a bit of luck, and monetizing their clout through modern media.

Learn about the journey of the most successful betting enthusiasts in the world and how they achieved their immense wealth through gambling.

1. Kerry Packer – Las Vegas’ Most Extravagant Player

Kerry Packer, born on December 17th, 1937, in Sydney, contracted polio at 8, which made his childhood difficult. Despite his early struggles, Packer developed a strong desire for gambling.

Packer loved playing Baccarat and often visited London’s MGM Grand, Bellagio, and Crockford’s. During one visit to Crockford’s, he lost $16.5 million in three days.

The Australian tycoon made his mark in the gambling world when he showed his mastery of Blackjack, reportedly winning around $20 – $40 million at the Las Vegas MGM Grand Casino in 1997.

Packer was among the most influential people in the world, creating and owning one of the biggest media companies worldwide, Publishing and Broadcasting Limited.

The media tycoon also made his mark in the sports industry, founding the World Series Cricket and providing funds for the World Rugby Corporation.

2. Tony Bloom – Richest Football Punter In The World

Tony Bloom graduated from The University of Manchester with a degree in Mathematics. He became known as “The Lizard” due to his calm demeanor while playing Poker for fun.

Tony Bloom graduated from The University of Manchester with a degree in Mathematics. He became known as “The Lizard” due to his calm demeanor while playing Poker for fun.

Throughout his career, he has accumulated around $2.5 million in winnings. He has competed in big events like the World Poker Tour and Poker Million IX, where he achieved a second-place finish.

This monumental win is a testament to how significant Horse Racing is to the English and the Brits, showing how vital the sport is to the history of the regions.

It’s important to note that most of Bloom’s wealth did not come from Poker. Instead, he founded his own consulting company, Starlizard, one of the world’s top betting firms, earning him millions.

Remember: Gambling laws vary across the US, as not all states allow wagers. It is crucial to consistently verify the legal status of gambling in each U.S. state before engaging in such activities.

3. Bill Benter – The Man Who Used Math To Beat The Bookies

Bill Benter, who gained fame for defying the Blackjack odds in casinos, and his Horse Race betting expertise, pursued a physics education at the University of Pennsylvania to refine his abilities.

Although he had no experience in casinos, Bill used Edward Thorp‘s book “Beat the Dealer” to master how to count cards successfully. He began winning thousands of dollars playing Blackjack in no time.

Benter became friends with another prominent gambler and mathematician, Alan Woods. In 1984, the two would profit from Hong Kong’s Horse Race betting using their mathematical models.

Did You Know?

Horse Racing is one of the only three legal forms of gambling in Hong Kong, alongside Football betting and the Mark Six Lottery.The Hong Kong Jockey Club (HKJC) monopolizes the region’s Horse Race betting market, managing its two racecourses: Sha Tin Racecourse and Happy Valley Racecourse.

In addition to his net worth of $1 billion, it is speculated that he earns around $100 million annually through Sports Betting using his software, which considers over 130 different variables.

4. Edward Thorp – The Godfather of Card Counting

Edward Oakley Thorp, known for his expertise in mathematics, is famous for creating the first card-counting system. Thorp is dubbed “The Man Who Beat The House.”

Thorp’s work went beyond gambling. His application of Probability Theory and statistical analysis to games of chance influenced various fields, including finance and economics. 

Warning

Although counting cards is technically legal, many casinos view it as cheating. Counting cards involves assigning values to cards and keeping track of high and low-valued cards dealt, which casinos and non-counters deem as manipulating the game.

Through his mastery of various games, Thorp achieved global renown for his victories against casinos, earning himself a place in Blackjack history as part of the esteemed Blackjack Hall of Fame.

His overall impact on gambling and probability is undeniable. He challenged the status quo, empowered players with knowledge, and paved the way for a more analytical approach to games of chance.

Fun Fact

Thorp’s book, “Beat The Dealer,” sold over 700,000 copies and made the New York Times bestseller list, with thousands of copies sold yearly since its release.Many gambling analysts credit the book for inspiring individuals to play Blackjack and other card games, increasing the casino industry’s player base and revenue.

Ultimately, Edward O. Thorp’s biggest win might not be a single, record-breaking sum of money but rather the lasting impact he’s had on how we understand and approach games of chance.

5. Andrew Black – The Programmer Who Predicted Horse Race Results

Black began his career in computer programming. He later became a professional bettor, developing an unconventional betting strategy of placing large bets on Horse Races. 

After his brother’s death, he briefly worked at a derivatives firm in London but left to pursue his passion for betting. Black later founded a software company, where he met Edward Wray while playing Bridge.

Wray saw the potential in Black’s algorithm, which could predict the results of Horse Races. He decided to invest in the project, and together, they founded an online betting exchange site called Betfair. 

Fun Fact

Betfair is among the highest-earning online casinos, contributing to the US Sports Betting revenue of $1.55 billion in 2023. 

Betfair Casino is the largest betting exchange worldwide, handling over 5 million transactions daily and boasting a market of over 1 million. The site is among the best platforms to offer Crash Gambling and other new and exciting games.

Short Disclaimer: Andrew Black is not to be confused with Andy Black, an Irish professional Poker Player.

6. Alan Woods – The Best Horse Handicapper of All Time

Alan Woods, an Australian professional gambler, accumulated most of his wealth by Horse Race betting in Hong Kong in collaboration with Bill Benter.

Launching his betting career as a skillful card counter and Blackjack player, Woods redirected his focus to Horse Racing and Sports Betting after encountering Benter during one of his visits to Las Vegas.

Woods was distinguished for his highly analytical approach to gambling, characterized by his mastery of Sports Betting and his constant quest for new strategies to gain an advantage over the house.

Fun Fact

One of the most intriguing facts about Horse Racing is that the most expensive horse sold was worth a staggering $70 million.Fusaichi Pegasus, the horse in question, was sold for $4 million as a yearling. However, after winning the Kentucky Derby, its value skyrocketed to an incredible $70 million.

7. Zeljko Ranogajec – The Most Enigmatic Bettor in Casino History

Zeljko Ranogajec, famously known as “The Joker” of gambling, amassed a substantial fortune through diverse gambling ventures, such as Keno, Blackjack, Sports Betting, and Horse Racing. 

Utilizing his outstanding math skills and expertise in banking, finance, and taxes, together with his time working in a casino, Ranogajec mastered the art of card counting at Blackjack tables.

Zeljko’s experience working Blackjack tables in casinos and expertise in various types of Blackjack games, such as California No Bust and Surrender Rules, was pivotal in his success at gambling.

Ranogajec, who also goes by the name of John Wilson, had gambling proficiency so remarkable that he faced bans from major casinos in both Australia and Las Vegas.

Like Bill Benter, The Joker partnered with Alan Woods to beat various casinos using complex mathematical models that they developed.

8. Billy Walters – The Most Successful Sports Bettor Vegas Has Seen

Billy Walters, an American entrepreneur and former professional gambler, rose to prominence due to his notable success in Sports Betting. Walters is dubbed as “The Most Successful Sports Bettor Vegas Has Seen.”. 

Walters was born in Munfordville, Kentucky, in 1946. He began gambling at nine and lost all his savings on his first bet. Billy is infamous among sportsbooks for his decades-long losing streak.

During the first two decades of his career, Walters had little success in gambling. However, after formulating a winning strategy for Sports Betting, he has been “in the red” only once in the last 39 years.

Side Note

In gambling terms, the phrase “in the red” refers to bettors who have wagered more money than what their bankroll has and are most likely in debt due to this.

9. David Walsh – The Eccentric Modern Gambler-Art Connoisseur

David Walsh developed an interest in gambling while studying at the University of Tasmania. He later created software that could predict the outcomes of Horse Races.

Thanks to his exceptional analytical abilities, Walsh was responsible for performing all mathematical calculations for the syndicate.

Despite his success in gambling, Walsh is notable for his disapproval of traditional gambling practices, which he has openly criticized.

Using his wealth for a different purpose, Walsh funded the creation of the Museum of Old and New Art (MONA) in Hobart, now recognized as one of Australia’s leading cultural institutions.

Fun Fact

Red Bull, a major sponsor in the world of esports for 2022 and 2023, began their involvement by enlisting the talents of David Walsh Bill.

10. Terrance Watanabe – The Biggest Whale in Gambling

Terrance Watanabe inherited his father’s Oriental Trading Company business, which sold arts and crafts, party supplies, school supplies, and toys. 

In 2000, Watanabe sold his company to pursue his love for playing Baccarat, Roulette, and Blackjack.

Helpful Articles

Baccarat and Roulette are the two most recognizable casino games worldwide. Both games are attractions due to their prestigious presentations and social appeal.But, there are key differences that players must learn about the two games to help bettors pick which game suits their playing preferences more.

He became famous for his significant gambling losses at the Wynn and Caesars Palace, casinos that played a role in the expansion of the Las Vegas Strip.

The “Whale” lost $127 million in Las Vegas in 2007 after placing bets totaling $835 million, the biggest losing streak in the city’s history. Watanabe owed Caesar’s Entertainment $14.7 million in credit, which he never paid back. He accused the casino of not returning 30% of his losses. 

Side Note

Las Vegas is renowned for its gambling scene, where fortunes can be made or lost instantly. While some of the first Las Vegas casinos are no longer in operation, new ones have taken their place, drawing both novice and seasoned gamblers from around the globe for many years.

In 2013, Caesar’s Entertainment was fined $225,000 for allowing Watanabe to gamble while intoxicated. Despite his high-stakes losses, Watanabe’s family supported him. He sought help with his sister at a treatment facility in Omaha and has not gambled since.

Did You Know?

Gambling addiction is very prevalent in the US; 1% (2.5 million) of the US population is diagnosed with harmful gambling, and 3 million adults are considered compulsive bettors.

11. Dan Bilzerian – The Controversial “King of IG”

Dan Bilzerian is a controversial figure on social media and the gambling world, earning him the nickname “King of Instagram” for his extravagant way of life.

Besides his online image, Dan indulged in exclusive high-stakes Poker, claiming to have won money as big as $50 million in one night.  In 2014, Dan Bilzerian tweeted that he had won $10.8 million while playing Poker.

Fun Fact

During an interview with Graham Bensinger, he revealed that he once bet $6 million (£4.4 million) on a coin toss, considered one of his wildest bets.

Bilzerian, however, remains a controversial figure, facing accusations of fabricating and exaggerating his narratives surrounding victorious bets.

On January 18, 2017, Doug Polk, a professional Poker player, released a YouTube video disputing Bilzerian’s ludicrous claims, establishing that Dan inherited his wealth rather than from playing Poker.

12. Phil Ivey – The GOAT of Poker

Phil Ivey is a professional gambler and Poker player from the United States who is widely regarded as one of the best all-around Poker players in the world.

Ivey’s feats are amazing because Poker is among the most complex games to play and win. With 2,598,960 potential hand combinations, success in Poker requires a balance of pure luck and extreme strategic prowess.

Ivey is often called the “Tiger Woods of Poker” because of his prowess and impeccable Poker skills, reportedly bagging $16.6 million from businessman Andy Beal in a single Poker session.

Phil holds 10 WSOP bracelets, the second-highest number of bracelets held by WSOP participants, and is tied with four other players. In 2017, the Phenom was inducted into the Poker Hall of Fame.

In addition to his success in competitive Poker events, Ivey has also had notable victories against casinos.

Ivey innately mastered how to play Baccarat and won $11 million playing the game at a London casino in 2012. However, a legal issue arose when the casino refused to pay his winnings. 

Eventually, the court ruled that Ivey had used illegal techniques to gain an advantage over the casino, which created significant controversy in his gambling career.

Quick Tip

In Poker, winning requires more than just sheer luck. Players can enhance their gameplay with practice and knowledge of different Poker strategies. Previously, players had to rely on coaches or books to gain this knowledge. Nowadays, anyone can easily access the best Poker training sites and courses online to learn the basics and complexities of the game.

13. Sam Farha – The Old School Gamber

Sammy Farha stands out as one of the most controversial figures in the Poker world, crafting his identity as an old-school gambler at the tables and beyond.

Farha’s first encounter with gambling happened in the ‘80s in Texas. Afterward, he found success playing Poker in Las Vegas and decided to move there to get a full experience of the casinos in the state.

For several years, Farha predominantly engaged in cash games and private sessions. However, in 1996, he expanded his horizons and entered the World Series of Poker (WSOP), clinching his first gold bracelet.

Fun Fact

The World Series of Poker is commonly regarded as the most notable Poker tournament in the world.Interestingly, the WSOP has awarded a whopping $3.29 billion in prize money since its establishment.

The turning point for Farha occurred in the 2003 WSOP, marking his significant presence in one of the most colossal Poker events ever held. 

14. Mikki Mase – The Self-Proclaimed Degenerate Gambler

Mikki Mase is among the most controversial high-rollers in the 2020s. Mase built a reputation on social media for his luxurious lifestyle, posting pictures of women and suitcases filled with cash.

Mase got in trouble at a young age. He once got locked up in prison for pushing drugs. Mikki turned things around when a friend offered him work at a tattoo shop in exchange for shelter.

Mikki Mase found gambling success after frequenting Los Angeles. Mase stated that his gambling ventures were always fruitful, winning $50,000 per trip at best. The “King of Baccarat” soon increased his wagers and won around $300,000 per trip.

The self-proclaimed “Degenerate Gambler” has yet to disclose his winning strategy in Poker and Baccarat. Mase has repeatedly stated that: “Playing cards is not about feelings. You can’t get a feel for the cards. It doesn’t work that way.”

The Ultimate Cash-In

Gambling has been popular for centuries. Some have turned it into a profession, amassing fortunes by making bold bets and using cunning strategies. 

However, gambling is risky, carrying the possibility of significant losses. It is essential to know when to resist the temptation to continue playing further, even after losing all the money.

While it can be a source of entertainment and wealth, by playing sharp and knowing when to quit, you can appreciate the thrill of gambling while minimizing the risks.