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The legendary wealth of the richest gamblers

People often say that the house always wins, and most of the time, that’s true. However, occasionally, a gambler with a lot of skill, courage, or money can turn the tables and make millions in the process. Many enjoy the thrill of gambling regularly, but some individuals consider beating the bookmakers to be their lifelong pursuit. Continue reading the following article from to discover the top 5 richest gamblers today!

The legendary wealth of the richest gamblers
The legendary wealth of the richest gamblers

What makes a successful sports bettor?


Successful sports bettors need self-control and discipline to adhere to their betting plans and focus only on meaningful wagers from a financial perspective. These are important traits that distinguish top sports bettors from recreational bettors, who are more spontaneous and emotional.

Strategic Thinking and Tactics

Top sports bettors stand out for their strategic thinking and tactics. They value considering and analyzing historical data as well as comparing odds and markets from bookmakers.

They often develop their own systems and compile Excel spreadsheets with automated formulas to evaluate important variables for them and lay the groundwork for their strategies. Additionally, they keep up with the latest statistical data and trends in sports betting.

Patience is crucial for these strategic experts as it helps them stay focused on long-term goals and pursue their tactics.

Continuous Learning and Research

In addition to gathering historical data, the most successful sports bettors analyze their betting to see what works and what doesn’t. When losses occur, they use their deep understanding to evaluate and improve their strategies. Research is consistent for them and not limited to specific game teams. It’s also about finding the best odds.

Online shopping is an important strategy for the best sports bettors. This tactic allows them to compare markets across different websites and select the most favorable ones. This way, in case of a win, the bettor earns more money and thus maximizes their efforts.

Not Afraid of Losses

Professional sports bettors are adept at managing money. They know how much they can afford to bet on a match, so losses don’t affect their balance. An example is Texas businessman Jim McIngvale, “Mattress Mack,” who lost $9.5 million on the Bengals to beat the Los Angeles Rams in this year’s Super Bowl and said he’d be “fine.” With a net worth of $300 million, he can afford to lose that amount.

How makes a successful sports bettor: Not Afraid of Losses
How makes a successful sports bettor: Not Afraid of Losses

Losses are part of the game, and the most successful sports bettors in the world know this and don’t despair over unsuccessful bets. However, the most important thing is that they know exactly how much money would be harmful to them if lost and never exceed that limit.

Accepting Uncertainty

No matter how much research and strategy you put into it, betting is still uncertain. Successful bettors deal well with uncertainty and understand that there’s no guaranteed win. That’s why they don’t take wins for granted or despair over losses.

Furthermore, their career is trial and error because no strategy or tactic is effective forever. Circumstances constantly change, and so do each player’s betting styles.


Because there are many variables involved, top sports bettors must trust in their strategies and reasoning to make decisions and execute moves that others may not even consider.

Confidence is an important trait that helps bettors stay strong. However, when it goes too far and isn’t supplemented by the knowledge that things don’t always go your way, it can lead to pursuing victory at any cost.

Self-Control of Emotions

Strategy, research, and risk acceptance will only get you so far. Another important factor that sets top sports bettors apart from your average “Joe” is their ability to understand and control their own emotions. A strategic sports bettor will never be blinded by a win nor be defeated by a loss, no matter how big, and will always be aware of and in tune with their mental state. Cathy Hulbert, a professional gambler who has made about $5 million playing cards and gambling, says she’ll decrease her bet amount if she gets too excited.

Richest soccer gamblers in the world

1. Matthew Benham – Net worth of Matthew Benham: $20 million USD

Matthew “Moneyball” Benham epitomizes the classic rags-to-riches narrative. After graduating from Oxford University in 1989 with a degree in physics, Benham left his comfortable position at Bank of America to pursue wealth through sports betting, eventually acquiring ownership of his beloved football club.

Transitioning from finance to analytics, Benham joined Premier Bet in 2001, where he honed predictive models using his financial background. Despite a short-lived apprenticeship under Tony Bloom, another successful football bettor, Benham departed the company in 2003.

Richest football gamblers in the world: Matthew Benham
Richest football gamblers in the world: Matthew Benham

His decision proved fortuitous as he became a millionaire bettor in 2004, founding his own sports betting organization, Smartodds. A lifelong fan of Brentford FC, Benham intervened in the club’s financial crisis in 2007, providing a loan to fans for club ownership.

When the fans defaulted on the loan in 2012, Benham assumed ownership. Leveraging his betting skills, he steadily improved the team’s value and performance, leading Brentford FC to compete in the Premier League.

2. Tony Bloom – Net worth of Tony Bloom: $1.3 billion USD

Tony “Lizard” Bloom, born in Brighton, stands as one of the most successful professional sports bettors. He currently divides his time between business ventures and managing two leading football clubs, Brighton & Hove Albion in the Premier League and Royale Union Saint-Gilloise in Belgium.

Bloom’s journey began with using fake IDs to bet on horse races as a teenager. Despite occasional setbacks, with a degree in Mathematics from the University of Manchester, he applied his knowledge to sports betting, becoming highly successful in the field.

Richest gamblers in the world: Tony Bloom
Richest gamblers in the world: Tony Bloom

Dubbed “The Lizard” for his cool demeanor in poker, Bloom reportedly won £2 million in a high-stakes poker game. While poker initially brought him success, Bloom later shifted towards business and investment, becoming a prosperous entrepreneur in the gambling and real estate industries.

He also manages two major football clubs and allocates a portion of his betting fortune to social causes, including supporting the construction of a Jewish school in Hove.

3. Bill Benter – Net worth of Bill Benter: $1 billion USD

Bill Benter is a professional sports gambler born in Pennsylvania, who became wealthy through horse race betting and wagering on various sports events. Benter graduated with a physics degree in 1977. His first foray into professional gambling was with blackjack in Las Vegas, where he excelled at card counting.

However, his encounter with Alan Woods shifted his focus to sports betting. Both became professional sports bettors and moved to Hong Kong in 1984. They devised a statistical model to predict winners in various sports events. He also collaborated with professional sports gambler Robert Moore.

Richest soccer gamblers in the world: Bill Benter
Richest soccer gamblers in the world: Bill Benter

Bill Benter has contributed to various charitable organizations and political groups. He was a donor for Barack Obama’s presidential campaign and the Democratic Party of Virginia. His philanthropy also extended to Rabbis for Human Rights and J Street. Ultimately, Bill Benter was recognized for donating $1 million to the University of Pittsburgh.

4. Haralabos Voulgaris – Net worth of Haralabos Voulgaris: $500,000 – $2 million USD

Haralabos Voulgaris has made a name for himself by participating in various sports events, especially in the NBA. His approach differs from those who bet on soccer, leaning more towards mathematics. Bob Voulgaris, a Canadian of Greek descent, began betting on sports, mainly NBA events, in the late ’90s. By 2000, he had accumulated substantial wealth and felt confident enough to wager $1 million in a single day.

Richest gamblers: Haralabos Voulgaris
Richest gamblers: Haralabos Voulgaris

His nickname is observing the coaching strategies of some head coaches. Bob Voulgaris is also passionate about poker, earning over $3 million from live tournaments over 14 years. On October 4, 2018, the Dallas Mavericks hired Bob Voulgaris as director of quantitative research and development. His tenure there ended on June 16, 2021, due to conflicts at the main office.

5. William Walters – Net worth of Billy Walters: $200 million USD

William Walters is an American businessman who made his fortune from betting on sports events. He’s also privileged to be considered one of the most successful professional sports bettors in Las Vegas, maintaining a winning streak for over 30 years. Billy Walters was born in Kentucky to an auto mechanic father and an alcoholic mother. His father passed away when Billy was only 18 months old, and he was eventually raised by his grandmother. However, she passed away when Billy Walters was 13.

He moved to Louisville and held two jobs. In 1965, William Walters worked as a car salesman, selling an average of 32 cars per month. He demonstrated an impressive work ethic, working 80 hours a week. However, simultaneously, Billy Walters began getting involved in sports betting.

Richest gamblers: William Walters
Richest gamblers: William Walters

William Walters left the auto industry to devote himself entirely to gambling in 1981. In 1982, he was convicted of a minor offense relating to gambling records in Kentucky. But Billy Walters quickly bounced back. Not long after, he decided to move with his family to Las Vegas.

That’s where he amassed wealth through sports betting. In the ’80s, William Walters joined the Computer Group, using computer analysis to make predictions in sports betting. This professional sports gambler had only one losing year in 39 years and is believed to have earned between $50 to $60 million in a winning year.

Unfortunately, Billy Walters was convicted of insider trading involving Dean Foods stock and sentenced to 5 years in prison along with a $10 million fine.


In summary, these five individuals epitomize the pinnacle of success in the realm of sports gambling, each with their own unique journey to wealth and recognition. Through innovative strategies, relentless dedication, and a deep understanding of their chosen fields, they have not only amassed significant fortunes but have also left a lasting impact on the industry. Their stories serve as inspiration for aspiring gamblers, highlighting the diverse paths one can take to achieve success in this dynamic and challenging field.

See more: Find out the list of best sports bettors in the world