Biggest Wins In the History Of Gambling

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As soon as you step into a casino or access a gambling site, you surely expect to win at least a few bucks. The truth is that everyone dreams of winning big at casino games. Whether you’re a newbie or an expert player, there’s always hope to win big time. This article will cover everything you need to know about the people who succeed in winning jaw-dropping millions at both land-based and online casinos. Check out their stories and learn everything you can for your next gameplay!

A Touch Upon Gambling

Gambling has become a very popular activity among people worldwide. If horse races were only available to an upper social class in the beginning, today, everyone has access to a whole new world of online casinos.

Gambling sites’ popularity grows every day thanks to the outstanding experience they deliver. At the best slot sites, a player might try out engaging titles that also give more chances of earning a substantial amount of money.

Besides this, many gamblers love the excitement and the thrill of the games and the casino bonuses. Whether it is blackjack, a game of poker, or slot machines at an online casino — there are a lot of opportunities to enjoy an exciting game with stakes as high as you’d like them to be.

Some players truly have fortune on their side, winning life-changing money. Yet, along with luck, they also had a great set of skills that recommended them as professionals.

To understand how skills and practice influenced their winnings, we’ve prepared a breakdown of each game category and a detailed story of their winners. This way, you’ll have all the advantages in one place to clearly see how to pull out your next gaming strategy.

Some Got Lucky at Slots

Online casinos won’t be successful without an extensive game collection. A study claims that, on average, 85% of the revenue is provided by these exciting games that you may also find at minimum deposit casinos.

Slot games are the most accessible form of gambling, and for that reason, they are a fan favourite. The truth is that new and experienced players can use a slot machine and eventually win some cash. It’s fast, engaging and colourful, and it tells you almost instantly if it’s your lucky day.

Someone got lucky at slots

Let’s see the people who managed to attract luck on their side gaining fantastic payouts. 

Anonymous Player: $39.7 million

The luckiest slot machine winner in gambling history is an anonymous software engineer. He tried these intriguing games for fun at the Excalibur Hotel & Casino. Little did he know that his tryout would pay out so well.

He started playing with $100, and won almost $40 million. This winning amount is considered the most significant ever slot win in the history of slot gambling.

Jon Heywood: $19 million

The 25-year-old soldier won the Mega Moolah jackpot 25 minutes after he opened an online player account. He has won $19 million in 25 minutes, changing online gambling statistics forever.

Thanks to this fortunate event, he even gained a spot in the official Guinness world record book. This is the largest slot machine win-win ever accomplished by an online player.

Amy Nishimura: $9 million

Even retired people can get lucky and win big. Amy Nishimura is a 71 years old lady who managed to win 8.9 million in just three hours by hitting the Megabucks jackpot at Fremont.

There’s also a funny side to this story, as this lady invested only $100 and had $40 to spare after she hit the jackpot. Also, she talked to the machines for more than three hours and eventually, they listened, giving her the best payout. 

John Tippin: $11.9 million

In 1996, John Tippin took the biggest slot machine win ever recorded for $9. He was only 50 years old and working as a postal worker. He took a trip to Las Vegas and wanted to relax with a casino game at Hilton.

He didn’t know how much hitting the Megabucks Jackpot just like in the movies and landing the millions on his last turn of the handle would change his life.

However, he wasn’t prepared for such a change and wealth proved to be too much for him. He even wrote a book about his struggles with isolation, financial woes, loss of friends, and paranoia after winning that jackpot, and he lost all his money to an extravagant lifestyle.

Another Anonymous – Australian this time

Your passion for blockbusters movies can really matter. At least it matters for this Australian gambler who won about $8 million on a Dark Knight slot machine. We may say that he started to build his own empire just like Bruce Wayne! 

Elmer Sherwin: $4.6 million

Elmer Sherwin is perhaps considered the luckiest man alive. Passionate about travel, he started a trip across the country together with his wife in their RV. They decided to make a stop in Las Vegas. He tried his luck at the Mirage, hitting the jackpot worth $4.6 million.

What makes his story special is the fact that sixteen years later, he got lucky again. The 76 years old won $21 million on Megabucks slot machine, located at the Cannery Casino & Hotel in Las Vegas. 

Did Someone Just Say Poker Winners?

Poker is a game you can enjoy both online at live dealer casinos or traditional establishments. This is a skill game and, as the saying states, “Poker’s a day to learn and a lifetime to master”, which is undoubtedly true.

Did Someone Just Say Poker Winners

Skill and luck are the perfect winning formula. When these two work together, the real magic happens, giving you a fantastic result as it did for the next poker stars. 

Antonio Esfandiari: $18.3 million

One of the biggest gambling wins ever was accomplished by Esfandiari, who won an incredible $18.3 million. The fortunate event happened during WSOP’s event called Big One for One Drop 2012.

The win also brought him a platinum bracelet, which was the second WSOP title for the 33-year-old Brit. This means that his total winnings were up to $23.2 million.

Daniel Colman: $15.3 million

He is the winner of the second-largest tournament in poker history called Big One for One Drop in 2014. Daniel is a professional player who is also highly talented.

Even though the winnings are pretty impressive, his most significant win in Las Vegas is actually the refusal to pose for the cameras.

Elton Tsang: $12.2 million

Elton enjoys the third-largest win in poker history that happened in Monaco’s Casino de Monte-Carlo. The 35-year-old Canadian businessman is also a talented professional poker player determined to follow his passion.

His skills and luck paid off in 2016 as, unlike the preceding WSOP tournaments, only 26 players entered the game this time. 

Jamie Gold: $12 million

With such a glorious name as Gold, it was almost predestined to win one of the biggest gambling wins. He is no ordinary player, as Jamie Gold is a 37-year-old television producer and talent agent. He triumphed at WSOP 2006, adding even more fame to his name. 

He concurred gradually on the largest-ever WSOP main event. Thanks to his unique profile, his victory remains legendary in the poker world.

Sam Trickett: $10.1 million

The same year Esfandiari triumphed at the WSOP, Sam Trickett, a 26-year-old, took second place. To that point, that was his most significant gambling win.

His career had seen a significant change. If in the beginning he started as a professional football player in England, he is today a successful poker pro player with a net worth of $5 million.

Martin Jacobson: $10 million

Martin Jacobson is not an ordinary player. He was only a trainee chef when he won the main prize at the 2014 WSOP Main Event. The then 27-year-old Swedish trainee chef spent 16 hours of gameplay to reach his winning goal. 

Justin Bonomo: $10 million

Justin’s story is also one with a peculiar twist. Bonomo said he had to borrow money to make the $1 million buy-in so he had to share his winnings after the roaring success.

Hossein Ensan: $10 million

He is the oldest poker player that won the main event, at least so far. The 55-year-old player won the 50th World Series of Poker after 101 hands played.

He is also the third and the oldest Iranian-born competitor to claim a poker title. The youngest player who won a poker tournament was Joe Cada, 21 at the time of the tournament. 

Those Who Found Success At Roulette

Roulette games rely on pure luck. Even though experienced players know that exceptional circumstances influence the outcome, the wheels may roll only to your fate. Given the past pandemic event, more winnings happened at online roulette casinos.

Those Who Found Success At Roulette

Let’s see how these “kings of the wheel” followed their intuition for success against all incredible odds.

  • Pedro Grendene Bartelle: Won $3.5 million in 2017 with an all-in bet on Red 32. Thirty-five to one payout turned his $100,000-worth chips into $3.5 million.
  • Sir Phillip Green: The British media mogul won $2 million in one of London’s most exclusive casinos—Les Ambassadeurs Club.
  • Charles Wells: Even if it happened in 1982, with today’s calculations, Wells’s winnings are worth $13 million. He inspired the artist Charles Coborn to write the song “The Man Who Broke the Bank at Monte Carlo.”
  • Mike Ashley: The owner of Newcastle United won $1.14 million by betting on Black 17 in 2008. It was a so-called complete bet on everything related to Black 17—James Bond’s pick.
  • Chris Boyd: He won $440,000 while betting his savings on the luckiest number in roulette — 7 Red. 
  • Joseph Jagger: He was a resourceful player who studied the roulette wheel in the Monte Carlo Casino in 1873. He discovered that the wheel is drawn towards some numbers, so he cashed in on it. He won $375,000, which in today’s money means millions.
  • Ashley Revel: He was only 32 years old in 2004 when he gambled his savings to win $270,000. He placed his bets on Red & and doubled the savings.
  • Sir Sean Connery: The famous actor beat the one in 50653 odds of winning on roulette and gained £27,000. The event took place at the Casino de la Vallee in Saint Vincent, Italy, in 1963.

Biggest Blackjack Winners Of All Time

Blackjack, also known as twenty-one, is a game that needs attention, strategy, and a little luck. There are many chances of beating the odds and winning the game at specialised blackjack sites.

Here are the winners who attracted winnings on their side.

Kerry Packer: $40 million

The biggest blackjack win in casino history was taken by Kerry Packer. The Australian billionaire played eight tables waging over $250,000 and won 80x times his bet.

Don Johnson: $15.1 million

The former corporate executive managed to win that amount by playing at three different casinos, Borgata, Caesars, and Tropicana.

He tested his luck for more than five months of constantly playing when suddenly, one night, he won $6 million.

Ken Uston: $4.5 million

He is the brilliant mind behind card counting. He did this starting in 1975 until 1981. It took casinos a while to understand what he was doing, and soon after, they created a ban to protect themselves.

Dana White: $2 million

In 2014, White, the UFC’s president, nearly got excluded from the Palms Casino because he was winning a high amount for more than three months in a row. Casinos fixed this by allowing him to bet a maximum of $25,000 per hand. 

The So-Called “Shoeless” Joe: $1.5 million

The 80-year-old gambler surprised everyone with his homeless look by betting with his social security check of $400. His story has become a legend at the Treasure Island Hotel and Casino as he managed to win $1.5 million before losing everything.

Ben Affleck: $800,000

Believing he was a natural in the game, the famous actor was caught card counting. He then got a lifetime ban from the Hard Rock’s blackjack tables but still won $800,000.

Michael Geismar: $470,000

During a 2012 business convention, Geismar almost won half a million. His lucky streak amazingly stretched over six hours, making him a celebrity at the Bellagio casino in Las Vegas.

Goksel Selay: $132,000

One lucky taxi driver from the United Kingdom, Goksel Selay, won a combined jackpot of $132,000. He said he dreamt of big money coming his way before winning, and, apparently, dreams do come true eventually! 

Gambling Winnings From Bets

A large part of the gambling world includes sports betting. Gamblers collect massive sums from various forms of betting, yet sports have a place in their agenda. Here are the winners of the biggest gambling winnings from bets.

Name Winnings & Bets Facts
Vegas Dave $2.5 million for $140,000 On his actual name Dave Vancea, placed his famous bet on Kansas City Royal back in 2015. He predicted the team’s victory in the World Series. 
Steve Whiteley £1.5 million for £2  The modest 61-year-old heating engineer managed to win a Tote bet. He guessed six winners in a horse race, a thing that even the most experienced gamblers could not predict. 
Fred Craggs  £1 million for £0.5  He placed only a 50p bet on eight horse races for his 60th birthday. Even though all horses he chose had low chances of winning, he won an incredible amount making him one of the luckiest winners ever.
James Adducci $1.2 million for $85,000 The 39-year-old day trader from Wisconsin used his savings to bet on his favourite player—Tiger Woods, who also made him a rich man. This is the biggest payout in golf betting history. 
Charles Barkley $800,000 for $500,000  Barkley happens to be an NBA professional and also a talented gambler. He got his biggest win in 2002 during the Super Bowl. He bet half a million and 14 points on the New England Patriots, and when they beat St. Louis Rams 20–17, he gained $800k. 
Darren Yates $765,800 for $86 1996 was the era of the biggest gambling wins. That year, Yates won about $765,800 on a sporting bet. He bet on Frankie Dettori’s seven consecutive wins at the Ascot Races.
Mick Gibbs £500,000 for £0.30  In 2001, he placed a mini-bet of 30 pounds with which he predicted the outcomes of as many as 15 different games. The odds of him winning were one in 1,666,666, yet he managed to win big time! 
Phil Mickelson $560,000 for $20,000  He wagered $20,000 on the Baltimore Ravens when they played the New York Giants for the 2001 Super Bowl. The odds of this happening were only 22 to one, and he got lucky.

Final Thoughts

Gambling is a way of entertainment, a fun way to spend your free time and win some extra money. While some games require a good strategy and top-notch skills, others will just pay out randomly. You faced the success stories of countless people; maybe now is your turn to get lucky.

If you feel fortune is on your side, try these games today and elevate your professional betting skills. At the same time, remember that responsibility is the key to a successful gambling career. Therefore, have fun, and place your bets, but play responsibly!

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