It does not matter if you are a newbie or an experienced sports bettor, you have probably heard of the term “Professional Sports Bettor”. You may even aspire to turn your betting into a more serious activity and maybe join the list of names on this page.
Here we are going to tell you the stories of the top professional bettors of all time (in our opinion). We hope these stories help you in your battle to beat the sportsbooks. We’ll also touch on important topics like betting systems, betting strategy, and bankroll management.
So read on to get into the thought process of some of the greatest gamblers of all time.
What is a Professional Sports Bettor?
Before we get into our top pro sports bettors, let’s answer that question.
Most bettors are termed shuffle bettors. They are constantly betting on one event after another. They are not using any proven betting system, and most likely not wagering the same stake or percentage of the bank on each bet.
Is that you? Whatever you take away from this guide, then solid bankroll management would be the key thing to learn and understand. We’ll cover that further down the page.
A professional sports bettor is someone who makes a living betting on sports. That usually means doing extensive statistics research, testing his/her betting models, and rigidly betting only when the odds present value.
5 Tips on How to Become a Professional Sports Bettor
If your goal is to become a pro sports bettor then these five tips will help you get started on that journey.
- Study the top professionals past and present, and find commonalities between all of them. If the majority are using a certain strategy or tool, you can bet (pun intended) it is because it works.
- Learn to show patience. This is similar to the story of the tortoise and the hare. Do not bet just for the sake of having a bet. Learn to be very selective, where possible focusing on just a couple of sports.
- Choose a bankroll strategy and stick with it. The two most common strategies are flat staking and percentage staking (link to bankroll management further down the page)
- Paper trade your selections. Paper trading is tracking your bets using pretend money. This is good practice to help you see the results of a potential strategy and if it is one you should stick with.
- Have a set amount for your betting each week, month, or year. Do not deviate from that amount. This helps you gamble responsibly.
Richard SmithSports Betting Editor
The Top 9 Pro Sports Bettors of All Time
We all know the names of the best NFL icons to step onto the gridiron, and players like Michael Jordan, Shaquille O’Neill, and Lebron James are legends on the basketball court.
But would you recognize the names of Billy Walters or Bill Benter? Maybe not.
1. Billy Walters (US) – Sports Bettor:
Biggest Bet Estimate: $3.5 million
Walters is known as one of the most fearless sports bettors ever, at times wagering millions of dollars per day. His methods combined statistical analysis with good old-fashioned networking to try and gain an edge on the sportsbooks.
He went through a period of making huge profits from the sportsbooks. However, it didn’t start that way as his first bet, money earned from a paper round was bet on the New York Yankees to beat the Brooklyn Dodgers in 1955. A bet that lost but fueled the young Walters to try again.
Billy Walters is another pro gambler to write a book. “Gambler: Secrets from a Life at Risk” was released in August 2023. It details his life story and includes two fascinating chapters on his secrets and strategies for sports betting.
Walters Strategy: Walters has been lauded for his methodical and highly analytical approach to sports betting, and this set him apart as one of the most successful bettors in history. His strategy was founded on the ability and deep understanding of statistical analysis, probability, and the ability to identify inefficiencies in betting markets.
Walters went as far as hiring his own team of experts. This included quant analysts, software and programming pros, and university-educated statisticians. This team was responsible for developing sophisticated models that could predict outcomes with remarkable accuracy. This is something many bettors are trying to achieve nowadays by using AI and ChatGPT.
One of his most potent weapons was a network of insiders and informants, providing him with valuable information that wasn’t available to the general public.
Although he was a heavy gambler, Walters was known for an extremely disciplined betting style, as he portrayed in this interview on the 60-minute show which involved placing large wagers only when he was confident in his edge, a lesson that any aspiring pro gambler should take note of.
2. Zeljko Ranogajec (Australia) – All-around Gambler:
Biggest Bet Estimate: $1 Billion per year
Ranogajec is a gambler known for a love of the ponies as well as frequent casino gambling, and he is another pro sports bettor who preaches the use of mathematical models to gain an edge over the sportsbooks and casinos.
Having studied in Australia, the Croation-born gambler and businessman now resides in London.
Ranogajec Strategy: Known as “The Joker,” Ranogajec became a master of leveraging mathematical models and analytical strategies, often referred to as advantage gambling. This methodology means identifying bets where the edge to the casino or sportsbook is low, meaning over time it produced a profitable gambling model.
Like Billy Walters, the Croat took his gambling exploits to a higher level by employing a team (you can see a pattern developing here) of analysts to look at statistics and probability. This was the angle he used to identify value bets that others might overlook.
He was a big bettor on horse racing and would go deep into analyzing a combination of track conditions, horse form, and jockey performance. These would then be fed into computer algorithms to process vast amounts of data, seeking out patterns and trends that could inform his betting decisions. Ranogajec’s ability to consistently win large sums is a testament to his strategic acumen and his dedication to maintaining an edge in highly competitive environments.
3. Bill Benter (US) – Horse Racing Bettor:
Biggest Bet Estimate: $200,000
Bill Benter was a physics student from Pittsburg, and very early on in his university days it was clear he was a gifted mathematician, and the young benter decided he wanted to use his talents to make some easy money.
This is exactly what he did, by going on trips to Las Vegas where he was a card counter and won large amounts of money. He had become very good and then invested in the book “Beat the Dealer,” by Edward Thorp. This took his skills to a whole new level and after several years, he was banned from setting foot in casinos ever again in Vegas.
A chance meeting in 1984 with another gambler Alan Woods, would be the birth of what became one of the greatest gambling stories of all time when both moved to Hong Kong to focus on horse racing betting.
Bill Benter Strategy: The Benter strategy in horse racing was centered around the use of sophisticated computer models to predict race outcomes with incredibly high accuracy. Benter was a pioneer in applying quantitative analysis to horse racing, developing algorithms that incorporated a wide range of variables, such as horse performance, track conditions, and odds fluctuations. Just four years after moving to Hong Kong, he had turned a $150,000 starting bank into $3,000,000.
His approach involved processing vast amounts of data to identify patterns and trends that others might miss, allowing him to place bets with a statistically significant edge. In Hong Kong, there is a bet called the Triple Trio. You have to guess the first three home in the correct order in three separate races. This was a progressive jackpot pool just like you might get at online casinos. The pool had soared to over $100 million as told by Bloomberg, and Benter and his partners had used their algorithm to place more than 50,000 bets. They ended up with 36 winning tickets. 35 of them were consolation prizes for picking two of the three legs correctly, the final one was the jackpot ticket that netted the team $16 million.
Benter had this obsession with breaking the code, and he did that on that euphoric night in Hong Kong on November 6th, 2001.
4. Barney Curley (UK/Ireland) – Horse Racing Bettor:
Biggest Bet Estimate: £100,000
Curley was a fearless gambler, risking, winning, and losing huge amounts of money on horse racing, but he was as sharp and shrewd as many Irishmen are and is revered by gamblers for the 1975 Yellow Sam coup which had the bookies reeling.
Even after that huge coup, Curley was responsible for orchestrating several combo betting coups that took millions from the bookmakers.
Curley was also known for his charitable work, particularly in Africa before he sadly passed away in 2021
Barney Curley Strategy: Barney Curley is famed for his meticulous planning and execution of legendary betting coups in horse racing. His strategy involves a deep understanding of the racing and betting industry, but his secret was in the art of handicapping.
Curley had numerous insider contacts in the 1980s and 1990s and owned many horses himself. It was these horses that his trainers would run over the wrong distances on the wrong ground conditions on tracks that would not suit.
Many of these horses would have had form figures of 000000 meaning they had finished down the field in all of their races. This meant that gradually, each horse’s handicap mark would come lower and lower. One such coup was a four-timer that cost the bookmakers an estimated number of between £2-£4 million.
The coup happened on an everyday Wednesday race day in the UK back in 2015. The four horses were:
Eye Of The Tiger – 10/1 > 1/1
Seven Summits – 7/1 > 9/4
Indus Valley 20/1 > 4/5
Low Key 7/1 > 4/7
Huge gambles on their own, but when combined, created one of the biggest payouts ever in UK horse racing history.
5. Haralabos Voulgaris (Canada) – Sports Bettor:
Biggest Bet Estimate: $1 million
Canadian Haralabos Voulgaris is known for his exploits as an expert in basketball betting, particularly on the NBA circuit. His prime skill was finding gaps in betting lines. He would take advantage of differences of opinion on sportsbooks and find value bets where others would bet on the other side of the spread lines.
Haralabos Voulgaris Strategy: Haralabos Voulgaris, also known as “Bob,” is renowned for his analytical approach to NBA betting, which has made him one of the most successful sports bettors in the field. His strategy involves a deep understanding of basketball statistics and the ability to identify inefficiencies in betting lines.
Voulgaris developed sophisticated models that incorporate player performance, team dynamics, and situational factors to predict game outcomes with high precision. His approach is data-driven, relying on quantitative analysis to assess the probability of various outcomes and identifying value bets where the odds are favorable.
Voulgaris’s expertise in basketball analytics eventually led to a position as an executive for the Dallas Mavericks, where he applied his skills to basketball operations and player evaluation. His success as a bettor and his transition to a professional role in the NBA highlight the power of analytical thinking and data-driven decision-making in both gambling and sports management.
6. Tony Bloom (UK) – Sports Bettor and Casino Gambler:
Biggest Bet Estimate: £400,000
Tony Bloom who is well known to sports fans as the owner of Brighton & Hove Albion is also an extremely shrewd gambler and businessman. He is widely given the nickname “The Lizard” for his calm and cool attitude to sports betting.
He has a love of soccer and this is his favorite sport to bet on along with playing high stakes poker.
However, a lot of his wealth stems from a private betting syndicate with high rollers as members. This syndicate has proven to be profitable year after year, which led to Bloom buying stakes in various properties and real estate projects. From there the rest is history.
Tony Bloom Strategy: Over the years, Tony Bloom has mastered both poker and sports betting, particularly in soccer. His sports betting strategy leans into the use of data analysis and the leveraging of statistical models to make strategic betting decisions. These models are focused on various team performances, player stats, historical head-to-head results, and short-term odds trends. Over the years, these have allowed him to identify value bets where the odds are favorable.
Bloom is a highly successful poker player, having won multiple six-figure paydays, with his best reported to be just under $1,000,000 for his win in the 2011 Aussie Millions Poker Championship, Melbourne in 2011. He has career earnings of just under $4,000,000 according to the poker data site The Hendon Mob. His poker strategy involves a deep understanding of game theory, psychological insight into opponents, and the ability to adjust his playing style based on his and other players’ table positions. His success in multiple arenas showcases his strategic versatility and why he is a popular character to the fans of his beloved Brighton & Hove Albion soccer team.
7. Jimmy “The Greek” Snyder
Biggest Bet Estimate: $10,000 (in 1948)
Jimmy Snyder, also known as “Jimmy the Greek,” was a well-known sports commentator and oddsmaker. Born in Steubenville, Ohio, in 1918, Snyder became a well-known figure in the world of sports betting and broadcasting. He gained fame in the 1970s and 1980s as a commentator on the CBS sports show “The NFL Today,” where he provided viewers with insights into game odds and predictions. His charismatic personality quickly made him a household name.
Jimmy Snyder Strategy: Jimmy the Greek rooted his sports betting strategy in his deep knowledge of sports and his ability to analyze various factors influencing game outcomes. He combined statistical analysis with intuitive insights gained from years of experience watching the NFL.
He had an uncanny knack for understanding the dynamics of betting lines and identifying value bets where the odds did not accurately reflect the probable outcome. Although his approach was not as data-driven as modern betting strategies, his ability to take information from different sources and his instinctive feel for the game made him a formidable oddsmaker. Snyder’s legacy lives on as a pioneer in bringing sports betting to mainstream television, helping to popularize the practice among the general public.
8. Gadoon “Spanky” Kyrollos
Biggest Bet Estimate: $800,000
Gadoon Kyrollos, better known as “Spanky,” is a highly successful professional sports bettor renowned for his expertise in leveraging technology and analytics to gain an edge in the sports betting market. Born in New Jersey, Spanky has developed a reputation for his innovative approach to sports betting. Particularly, in the realm of using software and algorithms to identify profitable betting opportunities. He has his own product on his website SpankOdds.com.
Gadoon Kyrollos Strategy: Spanky’s strategy revolves around the use of advanced technology and data analysis to inform his betting decisions. He uses sophisticated software to automate the process of identifying value bets across various sports using algorithmic output. He focuses on discrepancies between his models and the bookmakers’ odds. Spanky’s approach involves continuously refining these algorithms to incorporate the latest data and trends. This strategy allows him to stay ahead of the market.
He places a strong emphasis on betting discipline and managing his bankroll effectively. This ensures that he maximizes returns while minimizing risk. Spanky also values networking within the betting community to find a possible edge from news and information. His success is attributed to his ability to adapt to the rapidly changing landscape of sports betting, utilizing technology to maintain a competitive edge in an increasingly data-driven industry that is now venturing into the area of artificial intelligence.
9. Teddy “Covers” Sevransky
Biggest Bet Estimate: $800,000
Six years after graduating from the University of Michigan, Teddy Sevransky, better known as Teddy Covers, moved to Las Vegas to become a full-time sports bettor. While other professional bettors on this list may have kept a lot of their success private, Sevransky has been a prominent figure in the sports betting world, primarily through the media.
Sevransky’s writing has been featured in the New York Times, Wall Street Journal, Washington Post, Boston Globe, Las Vegas Review-Journal, and Playboy magazine. His TV highlights include CBS This Morning, CNBC, and PBS, to name a few. Bettors can also see Teddy Covers in action in the documentary “Life on the Line.” This followed Sevransky and other professional bettors maneuvering Las Vegas sportsbooks.
Sevransky is still an active pro bettor today. Teddy can be found selling picks to casual bettors on his website, where you can pay for more advanced advice, as well as offering odds analysis, shopping lines, and free picks on his YouTube channel.
How do Professional Sports Bettors Use Technology?
As you have read in the section above. The very best pro bettors use statistics and data analysis to make informed decisions on the bets they will place. So if they are doing it then it is wise for you to do it.
Even 5 years ago, getting this type of data would have been expensive and time-consuming to get. However, with the AI wave now in full flow, there are lots of tools that you can use to pull and analyze data. Several AI tools like Deepseek can help you build your own analytical software. This is without the need to be a computer whizz.
You can learn more about these tools in our guide on sports betting bots.
Top 5 Celebrity Sports Bettors from Around the World
Some of the most famous sportsmen and stars of the silver screen make our list of the top 5 celebrities who love sports betting.
This section is well worth taking note of as it contains some great points about betting strategy but also some strong messages about the need to gamble responsibly.
1. Michael Jordan:
The Chicago Bulls legend is well-known for his love of gambling. The award-winning documentary “The Last Dance” highlighted and reported some of his gambling exploits.
Jordan competed fiercely both on and off the court. He often backed up his golf game with high-stakes matches on the golf course. At one point, he wagered $300,000 on a single putt. When questioned about having a gambling problem, Jordan replied with a definitive “NO,” explaining that his issue was actually a competition problem.
He would regularly bet against the crowds at pro-am golf events, betting a $100 – $500 that he could hit the green on par 3 holes.
That sort of money is irrelevant to somebody like Jordan, it is the thrill of the victory that has been there since his competitive basketball days. It was once reported that Jordan had lost a staggering $1.25 million during a weekend of golf betting. However, that has not been factually proven.
Michael Jordon Strategy: Jordan’s approach to gambling boils down to his competitive nature and desire to beat anybody or any challenge he undertakes. Whether he is betting on golf, playing blackjack, or engaging in other casino games. Jordan’s strategy revolves around his deep confidence and willingness to take significant risks.
However, he also factors his fame into the equation. He knows that many of the people he bets against may be better in terms of skill, but they fear him just through reputation. Jordan is aware that this narrows the skill gap leading to value in the wagers he takes on.
Jordan’s approach is less about mathematical precision and more about the buzz of competition and the mind games that go with it.
At the end of the day, he is a legendary athlete who has not lost any of the appetite for winning.
2. Floyd Mayweather:
Mayweather was one sports icon who took his sport to a whole new level. Mayweather has helped boxing become a huge box office draw and no surprise considering a 50-0 record in the ring.
Since his retirement, Mayweather has taken to the sportsbooks for his thrill-seeking. He is known to wager huge sums on boxing, NFL, and college football.
Don’t underestimate Mayweather. His biggest reported win was over $1 million on an ordinary run-of-the-mill college football game, a sport where astute pro bettors also take advantage of discrepancies in lines and odds.
Floyd Mayweather Strategy: Mayweather builds his gambling and betting strategy around sports betting, particularly in boxing, where he places bets in the hundreds of thousands range. As a general sports bettor, he vocally celebrates his big wins and supports them with sound statistical analysis. As a boxer, he showcased his ring craft more than his power, although he achieved more than half of his wins by knockout. He wore down his opponents with ring movement and precise jabs, and when they tired, he landed the killer blow.
He has taken a similar approach to his gambling showing strategic thinking in selecting bets. However, he has that fearless streak of placing large wagers when he feels the odds are in his favour.
3. Wayne Rooney:
The former England, Manchester United, and Everton footballer has been known to frequent casinos and enjoy sports betting.
With fame and glory at a young age, and being constantly in the spotlight, gambling was an outlet for Rooney.
Rooney reportedly lost £500,000 in just two hours at a Manchester casino. He also lost hundreds of thousands of pounds betting on various sports while away with the England National team. Rooney’s betting definitely got out of hand. In a 2020 interview, he advocated for responsible gambling among young soccer players.
Wayne Rooney Strategy: It is pretty clear that Rooney did not have a strategy like the professional bettors that we highlighted earlier. This just goes to show that successful sports betting is not just about how much money you bet. It is how you evaluate your bets and manage your bankroll.
A lot of Rooney’s bets were of course on Football, and given his expert status, you would expect him to have been successful. However, this is a stark reminder that understanding core betting principles is more important than gut feel.
Rooney’s experiences serve as a reminder of the importance of discipline and strategic planning in managing the inherent risks of gambling, especially for those who engage in such activities frequently.
4. Ben Affleck:
As an Oscar-winning actor, Affleck is known for his skills on the silver screen. This was especially the case with the critically acclaimed Argo in 2012 which he produced and directed. He also played the lead part of an undercover CIA agent extracting US government employees from Iran.
From a gambling viewpoint, Affleck has participated in a number of professional poker tournaments. In 2004 won the California State Poker Championship in 2004, taking home $356,400.
Affleck is also unlike many celebrity sports and casino bettors. He was reportedly banned from playing blackjack at the Hard Rock Casino in Las Vegas for counting cards, a testament to his strategic approach to gambling.
Ben Affleck Strategy: Ben Affleck is well known for his strategic approach to blackjack. In the past he has applied card counting techniques to gain an edge over the casino. His overall strategy involves a deep understanding of the game’s mathematical underpinnings, allowing him to track the ratio of high to low cards remaining in the deck. This information enabled Affleck to adjust his bets and playing strategies accordingly, maximizing his chances of winning.
Affleck’s approach to gambling reflects a disciplined and analytical mindset, using skill and knowledge to overcome the house edge. In poker, Affleck applies a similar strategic focus, relying on his ability to read opponents and make calculated decisions to succeed in high-stakes games. His gambling activities underscore the importance of skill, patience, and strategic thinking. This is how he acheived success at the casino and in sports gambling.
5. Charlie Sheen:
The actor came to real prominence when playing the cocky young trader Bud Fox. He was trying to get in the good books of the trading magnate Gordon Gekko played by Michael Douglas in the 1987 film Wall Street.
That certainly gave an insight into Sheen on the screen but his off-screen gambling is also well documented.
Sheen had gone through a divorce with Denise Richards, the actress citing that he was gambling and losing up to $200,000 per week at the height of a gambling problem.
Sheen himself confessed to being a heavy gambler and suffering from gambling addiction.
Charlie Sheen Strategy: Charlie Sheen’s gambling strategy was nonexistent. As a continued thrill seeker and love of sports betting and high-stakes wagers, it was not based on a solid strategy like a professional sports bettor.
Over the last few years, Sheen has worked hard in many areas of his life and is now a reformed gambler. This is a lesson to anyone, that having a gamble should be just for fun.
Why Are Professional Sports Bettors Successful?
As we have seen with the stories throughout this page. Being successful in sports betting is about taking a statistical approach, using data, being analytical, and not just betting for the thrill of the action.
The stories of Billy Walters and Bill Benter underpin what it takes to become a successful professional bettor. The stories of Wayne Rooney and Charlie Sheen however, tell the story of the potential of addiction from gambling due to boredom.
5 Tips for Professional Sports Betting Success
Each of the biggest sports bettors we’ve featured has their weapon of choice when determining their wagers. These tips and tricks they use can lead to success once implemented. Here are a few sports betting tips and secrets our experts have extracted from researching our professional gambling icons.
Effective Bankroll Management
At the very beginning of this article, we talked about sharing information on betting strategies and bankroll management. It is these types of tools used by the top pro sports bettors.
The best sports bettors understand that the only game that matters is the bankroll numbers game. Without a growing bankroll, bettors can assume they aren’t getting the wins they need from their bets. After all, if you’re breaking even you haven’t begun to start winning.
This is where bankroll management comes in. Knowing the precise amount to wager when placing bets to ensure your bankroll grows, is something all of our pro bettors understand. It’s never about the game you’re betting on, it’s about making sure you’re money is growing with every win.
In-Depth Research Ahead of Time
If you’re a bettor who enjoys betting on one set of odds of one game with an offshore sportsbook, you’ll still be doing a fair amount of research ahead of time. But all sporting events have their own set of variables. Each one may contain a nugget of insight into how things will shake out.
The very basic idea of this concept is looking at a player or team’s home and away splits. Some basketball players play better with certain teammates or hit certain metrics when coming off the bench. Some teams cannot play in cold weather. This research can help you read a point spread better or lead you to better player props. This type of game information can be the difference between winning by one point or losing by 20.
Discipline and Separating Your Mind From Your Money
Week 5 in the NFL season shouldn’t feel like the Super Bowl to bettors. The key to keeping a clear head about the money you’re wagering and your betting strategy. Your research and strategy should lead your betting odds selection, not emotion. This is the main pitfall for bettors. To become a pro, you need to accept that this is your livelihood and that you’re self-employed, so you must stay disciplined and keep your emotions out of your bet slip.
Focusing on a Core Sport or Sports
The thinking behind this is that you gain an edge by focusing your resources and time on one core sport. If you remember the backgrounds of Billy Walters and Bill Benter, they had a focus on baseball and horse racing respectively.
Money Management
Top sports bettors do not wager beyond their means. They will either keep to a level staking plan or a percentage of their bank plan.
The only way they diverge or increase risk is by betting with 1,2 or 3 betting bank points, or 1,2, or 3 betting percentage points.
Richard SmithSports Betting Editor
What Are the Winning Percentages of a Pro Sports Bettor?
Pro sports bettors have to take risks like any gambler would. However, they use sound mathematics in terms of the number of bets they place, the odds at which they place them, and the staking.
The table below shows how making more bets at a lower success rate beats placing fewer bets at a higher success rate.
| % of Winning Bets | 50 Bets | 100 Bets | 150 Bets | 200 Bets | 250 Bets |
|---|---|---|---|---|---|
| 65.0 | 13.3 | 26.5 | 39.7 | 53 | 66.2 |
| 62.5 | 10.6 | 21.2 | 31.9 | 42.5 | 53.1 |
| 60.0 | 8 | 16 | 24 | 32 | 40 |
| 57.5 | 5.4 | 10.7 | 16.1 | 21.5 | 26.9 |
| 55.0 | 2.7 | 5.5 | 8.2 | 11 | 13.7 |
| 52.5 | 0.1 | 0.2 | 0.4 | 0.5 | 0.6 |
As you can see from the above table, placing 50 bets at a strike rate of 60% would have gained you 8 points profit. Placing 200 bets at 55% would have gained you an 11-point profit.
Responsible Gambling
Betting on anything is risky; even the pros know that. After all, not all of us have multi-million dollar contracts to fall back on. If your betting habits become overwhelming, know that you’re not alone and there are resources out there that can help. Responsible gambling is the key to a positive wagering experience!
We recommend contacting the National Problem Gambling Helpline at 1-800-GAMBLER if your betting gets out of hand. You can also find more information by visiting the official website or speaking to customer support at your preferred betting site!
