Only a select few are living the dream that every casino players have, beating the house. Certain individuals found a winner pattern, a profitable strategy, and incredible luck to amass an incredible fortune.
Do you think you have what it takes to follow in their footstep? Find out as we talk about successful gamblers' stories.
1. Edward O. Thorp
You may not be familiar with the name, but you should be familiar with the concept of "card counting" for blackjacks. Edward Thorp is a mathematics professor with a mathematics doctorate and physics master's degree. His talent and skill helped him develop a system of calculating the probability of a card to appear based on the ones that were dealt.
Players attempting to copy his strategy can read about it through a book he published. Thorp moved on from the world of blackjack tables to the risky world of stock markets where he uses his wits to make more money.
2. Bill Benter
William Benter has his professional gamblers' stories coincide with Alan Woods since the two became racing partners when they moved to Hong Kong in 1984.
Benter's analytical mind and mathematical skills allow him to develop robust analysis software for the horse racing industry, earning him $1 billion. His program allows any punter to spot factors that significantly influence a horse racing result.
3. Bill Kaplan
Found of the MIT Blackjack Team, Bill Kaplan and his crew are some of the top gamblers in the US who have had their story adopted to a Kevin Spacey movie called 21. In 1979, this group of students used a mixture of common card counting techniques along with their shuffle and ace tracking methods. Kaplan managed to get up to a 4% edge against the house, letting them amass a fortune.
Members of the MIT Blackjack Team separated and pursued other interests. One interesting trivia to note, a few former members of the team along with Bill Kaplan appeared in the 21 movie.
4. Daniel Negreanu
If you ask anyone to name one of the famous gamblers of 2020 or even the decade, you are likely to get Daniel Negreanu. Negreanu made a name for himself by winning six WSOP bracelets and two WPT championships awards. Chances are also high that he will be at the final table of most poker tournaments he attends.
Even if you have yet to watch a WSOP match, you know Negreanu from his participation in different poker TV shows. Negreanu also plays Hearthstone from his Twitch channel and in the Hearthstone World Championship during BlizzCon 2015.
5. Zeljko Ranogajec
A businessman by day, a gambler by night. Zeljko "the Joker" Ranogajec has the mathematical skill to gain an advantage over the world of banking and finances as well as the casino floor. Ranogajec managed a $1 billion annual betting turnover from playing across different Australian casinos while killing it at the blackjack tables.
Apart from casinos, Ranogajec also found his fortune through horseracing and sports betting. He utilized his complex betting system to know which small margins to beg big.
6. Phil Ivey
Named the Tiger Woods of Poker, Phillip Dennis Ivey Jr. is regarded as the best all-round poker player with 10 WSOP bracelets, a WPT title, and nine appearances on the WPT final tables.
One notable technique Ivey used to win $9.6 million from the Borgata Casino's baccarat table is edge sorting. Ivey made mental notes of subtle differences on the back of each card to identify them when dealt with.
7. Joseph Jagger
Back in 1881, there was a textile business owner named Joseph Jagger who is one of the first people to find and exploit within the roulette table. Jagger figured that the roulette wheel was not balanced properly and that there are numbers that the ball frequently lands on due to the surface condition.
Through his attention to detail, Jagger took home £80,000 that day and became one of the famous gamblers in the UK who has beaten the house.
8. Archie Karas
Anargyros Karabourniotis, or Archie Karas, began his gambling career upon visiting Las Vegas in 1990 with only $50 and a $10,000 loan from a friend. Within a couple of hours of playing at the Razz tables, he tripled his initial $10,000 bank loan. That night in Vegas was the start of his famous "The Run" period of his career where he won up to $40 million after three years.
Karas lived out the highs and lows of the most successful gamblers. He accumulated a total net income of nearly $40 million collected before his ban from any casino due to an incident in 2013.
9. Alan Woods
Starting as a casual player of slots and poker as well as horse betting during his college years, Woods only committed to a full-time gambling career after his wife left him in 1979. From then on, he became a professional blackjack player by using a card counting method he learned from his bridge player acquaintance.
Woods' main fortune came from horse racing where he used his mathematician skill and developed a pioneered quantitative gambling method. With a total net worth of AU$670 million, Woods became one of Australia's successful horse bettors.
10. Tony Bloom
Nicknamed the Lizard, Tony Bloom is a renowned Brighton sports bettor, poker player, football club chairman, and the owner of Starlizard.
While his poker career yielded a total of $1.5 million as of 2008, his real fortune comes from his other investments such as his company Starlizard that offer accurate sports betting consultations. Bloom is making more than £100 million through the company alone.
11. Andrew Black
While famous sports gamblers on this list made their fortune in beating the house, Andrew Black is the exception for creating the house by establishing the very first and largest exchange site: "Betfair". Black's gambling career was not as successful as others who found a fortune from making profitable bets.
Instead, he took upon a bigger gamble by investing all of his life savings and looking for other investors to create a sports exchange that uses moneymaking betting software. Betfair went live in 2000 and drew millions of punters around the globe. Black's net worth in 2020 is at £500 million thanks to the risk he took.
12. Billy Walters
Billy Walters gambling story was all about getting back up no matter how many times you fall. At the age of nine, he lost his hard-earned savings on the 1955 World Series bet and continues to lose money well onto his young adult years. Walter's luck turned around upon his visit to Atlantic City where he and a gambling partner took advantage of a roulette table with a wheel bias. Both of them won $3.8 million that night, but for Walter, it was only just beginning.
Joining the Computer Group that uses computer hardware to make sports outcome analysis in the 1980s, Walters began his 30-year win streak. In a profitable year, Walters claims he can get $50 - $60 million.
13. Chris Moneymaker
Christopher Bryan Moneymaker (actual name) made his debut in the 2003 World Series of Poker by winning an $86 satellite tournament prize through PokerStars. Lou Diamond, a professional sports handicapper, caught wind of Moneymaker's skill and considered him "Dark Horse to win the whole tournament".
Moneymaker managed to make it to the final table and win the tournament's first prize of $2.5 million. He turned his back on his accountant career and never looked back as he lived a successful career as a professional poker player. In 2019, Moneymaker got the honor of being inducted into the Poker Hall of Fame.
14. Chris Ferguson
One of the WSOP popular personalities is Christopher Philip Ferguson who is known for his signature hats. During his college years, brushed up on his poker skills through an IRC poker room and participated in live tournaments held in California.
Ferguson talks and reacts less to avoid giving out any psychological tells. By using a mathematical method with a backing of game theory knowledge through developing computer simulations, Ferguson took home six WSOP bracelets. By 2017, he won a total of $8.9 million from live tournament winnings.
15. Patrik Antonius
Before engaging in a full-time poker career, Patrik Antonius was a tennis player, a coach, and even a model. Life took a major turn for Antonius due to a back injury that saw him moving from the tennis courts to the Monte Carlos casino floors and poker tables.
Antonius managed a successful poker career with total live earnings of more than $12 million. He is also the highest-ranking Finnish professional gambler in the world based on all-time money rankings.
16. Don Johnson
What set Don Johnson apart from other professional blackjack player is his way of making a fortune on the tables without using any card counting skill. Instead, he asked to use a blackjack rule that will set the house with a 0.26% house advantage and a loss rebate deal with the casino.
Successfully getting the terms he wants, Johnson managed a "positive expectation bet" that would give him a better edge due to the limited loss. Johnson took home $15 million thanks to that player's edge.
17. Standford Wong
John Ferguson or Standford Wong made a name for himself with his professional gambling books, including his Professional Blackjack book. Wong has helped numerous novice and experienced players over the years with 14 of his books that tackled blackjack, craps, video poker, and more.
Wong became the go-to consultant for any blackjack writer and was the first to create an odds computation software for blackjack.
18. Phil Hellmuth
Nicknamed the Poker Brat, Phil Hellmuth is a heavyweight in the WSOP tournaments with 15 bracelets to his name. His nickname comes from his intense reactions to bad beats and behavior.
Despite the attitude, Hellmuth can walk the walk with total live earnings of more than $24 million. Hellmuth also ranked first for Wisconsin's professional gamblers in terms of all-time money made.
19. Bryn Kenney
After a competitive Magic: The Gathering TGS career, Bryn Kenney got his start in a poker career by attending the East Coast Poker Championships 2007. He earned a coveted WSOP in the 10-Game Mix Six-Handed even in 2014 and took home $153,220.
What makes Kenney worth adding to this list is his incredible payout of £16 million prizes from the Triton Million for Charity Event. With a total live tournament winning of more than $55 million, Kenney ranked 1st among the US all-time-money ranking.
20. Vivek Rajkumar
Rajkumar was an underdog upon entering the World Poker Tour Borgata Poker Open Main Event in 2008 and took home $1.4 million. His win was a massive achievement at that time considering he just turned into a full-time poker player in 2006.
When you consider the ranking of India's highest gambling earners, Rajkumar is India's biggest gambler with a total earning of $8 million.
Whether a gambler has the mathematical skills or method to increase their edge, it is all about taking a large risk and gain an amazing return. It does not hurt to read up on blackjack card counting strategies or sports betting analysis to improve your odds and join the handful of successful gamblers on this list.
This article was published on February 12, 2021, and last updated on October 26, 2022.