The Biggest Gambling Wins – Top Land-Based and Online Gambling Wins

Every gambler dreams of hitting the jackpot, retiring, and living the good life. Although it is rare, there are instances where individuals have become millionaires overnight through winning the lottery or succeeding in poker. In this article, we will explore the fascinating world of these extraordinary stories and delve into the biggest gambling victories.

Published: 13th December 2022

Prepare yourself for an in-depth compilation showcasing the most significant wins in the history of gambling. You will have the opportunity to learn about skilled professional players and those who were incredibly fortunate, proving that anything is possible. Use the quick navigation below to easily navigate through the various sections.

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Top Gambling Wins in History

It goes without saying that the majority of the most significant gambling victories in history have occurred in brick-and-mortar gambling establishments. However, the most impressive online gambling victories are just as noteworthy, so in this blog post, we will examine both. Additionally, you will discover the greatest gambling victories ever in lotto, poker, blackjack, slots, roulette, and even sports. Therefore, keep reading for more information.

Examine our comprehensive list below to gain an understanding of the various categories we will cover in this blog post and the format it adheres to. Feel free to utilize our list to quickly navigate through the page and find your favorite sections.

The Biggest Land-Based Gambling Wins

Within the subsequent paragraphs, you will discover information concerning some of the most significant triumphs in the realm of gambling, and you will have the opportunity to peruse remarkable accounts of how both renowned proficient participants and their polar opposites – individuals who relied solely on fortune and nothing else – transformed into millionaires practically overnight. In each classification, we will acquaint you with the three most noteworthy successes, so keep your eyes peeled.

The Biggest Land-Based Lotto Wins

The Mega Millions jackpot of $1.337 billion was recently claimed in July 2022. There is limited information available about the unidentified individual from Chicago, Illinois, except for the fact that they must be elated to join the ranks of the most significant lottery victories in history and amass such a vast fortune.

Coming in second place for the largest lottery wins is the Mega Millions jackpot of $1.537 billion, which also holds the record for the largest jackpot won with a single ticket. Although the fortunate winner has opted to remain anonymous, it is widely known that the winning ticket was purchased in South Carolina.

The $1.586 billion Powerball jackpot that was won in 2016 holds the title for the largest lottery jackpot ever won, making it one of the most significant gambling wins in history. The three fortunate winners from California, Florida, and Tennessee divided the prize, each receiving approximately $533 million.

For those interested, be sure to visit our blog for additional notable gambling successes and plenty of fascinating information on the topic.

The Biggest Land-Based Poker Wins

After three days of intense competition, Aaron Zang emerged victorious at the renowned 2019 Triton Super High Roller Series, taking home an impressive prize of $16,775,820. Bryn Kenney secured the second position, while Dan Smith secured the third spot. Initially, Kenney held a substantial chip lead of over five to one, but Zang remained composed and patient, ultimately claiming the coveted first place.

In the memorable 2012 WSOP Event, named “The Big One for One Drop,” Antonio Esfandiari triumphed over 48 other skilled players in a grueling three-day battle, earning a staggering $18,346,673. Throughout the tournament, Esfandiari appeared remarkably serene and tranquil, as if he possessed foresight into his forthcoming victory.

Bryn Kenney, who is considered to be one of the most skilled poker players ever, came in second place at the Triton Super High Roller Series in 2019 but managed to claim the largest portion of the prize money, taking home an impressive sum of $20,563,324. Despite not securing the top spot in this particular event, Bryn Kenney’s outstanding performance allowed him to surpass Justin Bonomo on the all-time money list and claim the coveted first position.

The Biggest Land-Based Slot Wins

In 1998, a retired flight attendant who prefers to remain anonymous achieved an incredible feat by winning a staggering $27,582,539 while playing the Megabucks slot game at the renowned Palace Station Resort in Las Vegas. What makes this victory even more astounding is the fact that just a few months prior, she had already experienced a stroke of good fortune at the same casino, pocketing a noteworthy sum of $680,000 while playing the popular Wheel of Fortune slot game. It’s hard to find words to describe the sheer luck and serendipity that accompanied her remarkable winning streak!

Cynthia Jay-Brennan, a cocktail waitress, became the lucky winner of a staggering $34.9 million at the renowned Desert Inn Casino in Las Vegas. After finishing her shift, she decided to visit the casino and join in the celebration of her future mother-in-law’s birthday. Little did she know that within an hour, her life would change forever as she hit the incredible jackpot on a Megabucks slot machine. However, tragedy struck a few weeks later when Cynthia and her sister were involved in a car accident, resulting in the loss of her sister and leaving Cynthia paralyzed. Despite her devastating circumstances, Cynthia chose to use a significant portion of her winnings to support charitable organizations that assist individuals with disabilities.

Among the plethora of monumental gambling victories in the realm of slot machines, one particularly stands out: the remarkable $39.7 million jackpot secured by an anonymous software engineer at the Excalibur Casino in Las Vegas in 2003. To this day, it remains the most substantial slot win in history, leaving an indelible mark on the gambling world.

The Biggest Online Gambling Wins

It’s common knowledge that online casinos are gaining popularity among players. In addition to the wide selection of games, their easy accessibility, and numerous other advantages, they are gradually becoming the preferred choice for gambling. Therefore, let’s take a closer look at the remarkable and lucrative biggest wins in online gambling that we assure you will be equally impressive.

The Biggest Lotto Wins Online

This anonymous player managed to win a staggering amount of $23.5 million while playing the popular Mega Moolah slot game at the renowned Grand Mondial online casino. The incredible win, which occurred within a mere 50 spins, quickly garnered global attention and even earned a spot in the prestigious Guinness Book of World Records. Despite this newfound fame, very little is known about the lucky individual who is now officially a millionaire. If you’re curious to learn more about Mega Moolah, the beloved game that made this player’s dreams come true, be sure to check out this expert review.

The second place on our list of big wins in online lotteries goes to a player from Belgium who, in late April 2021, won a staggering $23.6 million at Napoleon Sports and Casino. This player is also a Guinness World Record holder for the largest online gambling win and was playing his favorite game, Absolootly Mad: Mega Moolah, when he hit the massive jackpot after just a few games.

Another remarkable addition to the history of big gambling wins is the Guinness World Record set by Lottoland for the largest online gambling payout ever, which amounted to $105,121,000. Lottoland Group, which includes Lottoland Limited and EU Lotto Limited, operates a platform where players can bet on lottery outcomes. The lucky winner of this record-breaking EuroJackpot win is Christina, a 36-year-old cleaner from Berlin.

The Biggest Poker Wins Online

In 2009, there was a game of Omaha Hold ‘Em Poker between Viktor Blom and Phil Ivey. This game is similar to Texas Hold ‘Em Poker, and the stakes were set at $500 / $1000. Viktor managed to defeat his opponent and walk away with a grand total of $1,127,955 in winnings. This victory came after a recent loss to Patrik Antonius, which we will discuss further in the next paragraph.

Shortly before the match with Phil, there was a legendary battle between Patrik Antonius and Viktor Blom in 2009. Once again, they played Omaha poker with the stakes set at $500 / $1000. In the end, Antonius emerged as the victor and claimed the largest pot in online poker history, amounting to $1,356,946.

Recently, in early 2022, Tony G (Tony Guoga), a professional poker player and politician, achieved a remarkable feat by setting a new record for the largest online poker hand ever won. Tony G participated in a high-stakes Pot Limit Omaha Poker game on CoinPoker, an online platform that utilizes cryptocurrency. In this intense 3-handed game with stakes ranging from $5000 to $10,000, Tony G emerged victorious, claiming an astounding pot of $7,750,652.

The Biggest Slot Wins Online

In 2016, D.P., an online player, achieved the incredible feat of winning the Mega Moolah jackpot, which amounted to a staggering $11.6 million. This triumph marked the largest victory ever recorded on a mobile device, showcasing the immense potential for success that exists within the realm of online gaming. With the constant influx of new mobile users, it is not inconceivable that the next record-breaking win could be just around the corner. Perhaps it’s time to test your luck and try your hand at one of the premier casino apps available to players in the United Kingdom.

Fast forward to March 2022, and another major win has captivated the online gaming community. Tyler Niknam, more commonly known as Trainwreck, emerged victorious with a mind-blowing prize of $22.5 million. What sets this win apart is the fact that Trainwreck achieved this cosmic triumph without hitting a jackpot. As a result, he now holds the distinction of claiming the largest non-jackpot online slot win in history. This monumental achievement serves as a testament to the limitless potential for success that awaits those who engage in online gaming.

This incredible triumph is one of the most monumental successes in the history of gambling and is credited to a Finnish bettor who played the Mega Fortune slot game at an online casino based in Scandinavia. The magnificent prize of $24 million was won with a mere $0.25 wager during the bonus round. Despite taking place in 2013, it remains the largest online slot victory to this day.

In conclusion, we highly recommend checking out our article on the most impressive online slot victories, where you’ll find the greatest rewards and the highest Return to Player (RTP) percentages.

The Biggest Blackjack Wins

When it comes to casino games, many players choose blackjack as their first option. The reason behind this choice is not only because blackjack is easy to play but also because it offers the best odds of winning, with a mere 1% house edge in most casinos. Another advantage of playing blackjack is that you are only competing against the dealer, which increases your chances of winning. If you are looking for a profitable game to play, blackjack is definitely your best bet, as long as you have a strategy in place. Below, we present the top 3 biggest blackjack victories in the history of gambling.

The CEO of Heritage Development, Don Johnson, was not only a millionaire, but also a highly skilled blackjack player. Renowned for his exceptional mathematical abilities, he managed to win a staggering $15 million over a period of five months. His strategy involved sticking to the most advantageous house rules and splitting every high hand into four before doubling his bets. It was undoubtedly his unique playing style that enabled him to achieve such remarkable wins, but unfortunately, it also resulted in him being banned from playing blackjack at the casino.

In 1991, Kerry Packer, an Australian entrepreneur, entered a casino and departed with $7 million, all thanks to blackjack. On another occasion, he managed to win an astonishing $40 million in just 40 minutes at the MGM Grand Casino in Las Vegas. His strategy involved playing eight hands simultaneously on the same table and placing a substantial $250,000 bet on each round.

Finally, we would like to discuss the famous MIT Blackjack Team, which served as the inspiration for the popular film 21. In case you are not familiar with them, this team was under the leadership of Bill Kaplan and comprised of a group of students who utilized advanced mathematical tactics in order to outsmart casinos in the game of blackjack. The team was active for a number of years and managed to accumulate a staggering sum of over $50 million in winnings, solidifying their status as legendary figures and holding the record for the largest gambling victories ever achieved in the realm of blackjack.

The Biggest Roulette Wins

There is a certain allure to roulette that ignites excitement and captivates players. The iconic roulette wheel has become synonymous with casinos and holds a special place in the world of gaming. Join us as we delve into the fascinating stories behind the three most colossal roulette victories and the skilled individuals who achieved them.

Charles Wells, who was often referred to as ‘Monte Carlo Wells’, gained notoriety as an English gambler and con artist. He is also the inspiration behind the popular song ‘The Man Who Broke the Bank at Monte Carlo’. In 1891, Charles made his way to the Monte Carlo Casino Resort for a game of roulette, where he astonishingly won 23 out of 30 consecutive spins, accumulating nearly a million francs. However, this impressive feat did not satisfy the ambitious player, as he soon returned to the casino and, relying solely on luck, managed to amass another million francs.

In 2008, Mike Ashley, a billionaire entrepreneur and former owner of the English Premier League club Newcastle United, entered London’s Fifty Casino for a brief gambling session. During his time there, Ashley placed a bet of over $550,000, covering all possible combinations such as splits, corners, streets, and six-line bets. Additionally, he placed a straight-up bet on the number 17. Remarkably, within a span of less than 15 minutes, Ashley walked away from the casino with a staggering sum of $1,493,875.

Another prosperous businessman named Pedro Grendene Bartelle had a similar stroke of luck while visiting the Punta del Este casino in Uruguay. Bartelle decided to test his luck on French Roulette and placed most of his $500 chips on the numbers within the third dozen. Furthermore, he concentrated a significant portion of his chips on the number 32. Astonishingly, when the ball landed on that exact number, Pedro transformed his initial $35,000 into an astounding $3.5 million.

The Biggest Sports Gambling Wins

When discussing the most impressive victories in gambling history, it would be remiss not to mention the remarkable successes in the world of sports betting. In this final paragraph, we will explore the three most significant triumphs in sports gambling, so brace yourselves.

One of the most renowned gamblers in Las Vegas, known as Vegas Dave (whose actual name is Dave Oancea), achieved an extraordinary feat during the 2015 baseball season. He placed a staggering bet of $140,000 on the Kansas City Royals to win the World Series and ended up walking away with a jaw-dropping $2.5 million. Due to the immense size of his wager, he had to split it amongst 15 different casinos, as none of them were willing to accept such a colossal bet. Nevertheless, he navigated this hurdle and emerged victorious, leaving everyone in awe.

Billy Walters, a well-known poker player, placed a massive bet of $3.5 million on the New Orleans Saints in their Super Bowl XLIV match against the Indianapolis Colts. In a stunning victory, the Saints emerged as the winners of their first-ever Super Bowl with a score of 31-17. While the exact amount of his winnings remains unknown, it is undeniably one of the most significant gambling triumphs in sports history.

At the top of our list of the greatest sports gambling victories is an unnamed individual, supposedly from Eastern Europe and approximately 30 years old. This fortunate bettor raked in an astounding $14 million during the 2017 World Series, thanks to a string of successful wagers. The final bet, placed on the game between the L.A. Dodgers and the Houston Astros on November 1st, 2017, secured his incredible winnings.

The Top 3 Largest Gambling Wins in History

We’re sure those incredible prizes have really sparked your imagination. After covering a wide range of games and categories, it’s time for the most exciting part. Here is our compilation of the three most monumental wins in the entire history of gambling.

Evidently, nothing can surpass the Mega Millions jackpot – not even blackjack strategies or elaborate schemes, let alone the enormous jackpot prizes. The bottom line is that you should play the lottery more often, as you never know when fortune will come knocking at your door.

Biggest Gambling Wins FAQ

Hopefully, this article has provided both entertainment and intrigue, while also offering comprehensive answers to all inquiries about notable gambling victories. However, we understand that there may still be lingering curiosities or overlooked details. To address this, we have compiled a list of commonly asked questions that you can consult for additional information.

1️⃣ What is the biggest gambling win on poker?

Bryn Kenney, a skilled poker player, emerged victorious in the Triton Super High Roller Series in 2019, raking in an astonishing $20,563,324. To delve deeper into the realm of poker fortunes, check out the most monumental triumphs in the game’s history highlighted earlier in this piece, or explore the most captivating online poker victories.

2️⃣ What is the biggest sports betting win in history?

3️⃣ What is the biggest slot jackpot win ever?

4️⃣ What is the biggest ever online slot win?

In 2013, a Scandinavian online casino witnessed an incredible win when a Finnish gambler hit the jackpot on the Mega Fortune slot game. With a mere $0.25 bet during the bonus round, the lucky player walked away with an astounding $24 million! This remarkable story serves as a testament to the potential of online slots to deliver life-changing wins. If you’re looking for inspiration, be sure to explore our list of the top 3 biggest gambling victories on slot machines.

5️⃣ What is the biggest gambling win on roulette ever?

The person who achieved the biggest roulette win in history goes by the name of Pedro Grendene Bartelle, a prosperous entrepreneur who managed to transform $35,000 into a staggering $3.5 million. Take a look at the three most significant victories in roulette gambling to explore more remarkable successes and the individuals responsible for them.

Pedro Grendene Bartelle, a triumphant businessman, became known as the gambler who accomplished the largest roulette win ever by turning $35,000 into an impressive $3.5 million. To delve into additional incredible triumphs and their respective players, make sure to review the top three most substantial gambling wins in the game of roulette.