Biggest Poker and Casino Winnings

Luck never gives. It only lends. Do you believe this to be true? Those with the biggest gambling wins beg to differ. Some of them even won despite very low odds several times in their lifetime.  But how did they do it? Are these winners good players, lucky, or both? Check out the stories of […]

Luck never gives. It only lends. Do you believe this to be true? Those with the biggest poker and casino wins beg to differ. Some of them even won despite very low odds several times in their lifetime. But how did they do it? Are these gambling winners good players, lucky, or both? Check out the stories of their biggest wins and judge for yourself.

Biggest Poker Winners  

As the saying goes, “Poker’s a day to learn and a lifetime to master.” And unlike getting that lucky big win on slot machines, poker requires actual skill.

Skill and luck both contribute to winning. The real magic happens when these two work together, as it did for the following poker celebrities.

Antonio Esfandiari: $18.3 million

His big moment happened during WSOP’s event called Big One for One Drop 2012. Esfandiari won an incredible $18.3 million, which is, to this day, one of the biggest gambling wins ever.

The win came with a platinum bracelet, which was the second WSOP title for the 33-year-old Brit. Therefore, his total winnings summed up to about $23.2 million.

Daniel Colman: $15.3 million

Daniel won the second-largest tournament in poker history—Big One for One Drop 2014. This 23-year-old professional player is extremely talented. Yet, the most memorable thing about Colman’s biggest win in Las Vegas is his refusal to pose for the cameras.

Elton Tsang: $12.2 million

The third-largest win in poker history happened in Monaco’s Casino de Monte-Carlo. The winner was Elton Tsang — a 35-year-old Canadian businessman and professional poker player. And unlike the preceding WSOP tournaments, only 26 players entered the game in 2016.

Jamie Gold: $12 million

One of the biggest gambling wins was made by an unlikely player. Namely, Jamie Gold, a 37-year-old television producer, and talent agent, triumphed at WSOP 2006.

Critics say that he bluffed his way to the top, concurring the largest-ever WSOP main event. Because of his profile, Jamie’s victory is legendary in the world of poker.

Sam Trickett: $10.1 million

When Esfandiari triumphed at the WSOP, this 26-year-old took second place. This was the biggest gambling win of his career to that point.

Trickett has come a long way since his days as a professional soccer player in England. Today he’s a successful poker player with a net worth of $5 million.

Martin Jacobson: $10 million

Martin Jacobson was a 27-year-old Swedish trainee chef when he won the main prize at the 2014 WSOP Main Event. It took him 16 hours of gameplay to reach his dream.

Justin Bonomo: $10 million

This is yet another one of the few big casino wins with a peculiar story. Namely, Bonomo had to borrow money to make the $1 million buy-in, so he ended up sharing his winnings. ESPN estimates that his earnings are higher than Daniel Negreanu’s.

Hossein Ensan: $10 million

Hossein Ensan (55) is the oldest poker player to win the main event so far. He won the 50th World Series of Poker after 101 hands played.

So far, Ensan is the third Iranian-born competitor to claim a poker title. He’s also the oldest. The youngest player to win a poker tournament was Joe Cada, 21 at the time.

Biggest Gambling Winnings From Bets 

Nothing boosts the sports viewership statistics like betting. While the saying “nobody has ever bet enough on a winning horse” holds true, gamblers still collect massive sums from various forms of betting.

Some claim to have the winning formula, while others have a certain “sixth sense.” Recently, this was the case with an anonymous 69-year-old furniture retailer. He won $6.18 million on a Super Bowl bet—one of the biggest gambling wins in 2021.

Sports betting is prevalent everywhere, but Las Vegas still holds the throne. Namely, Westgate Las Vegas SuperBook is the largest sportsbook in the world.

Vegas Dave: $2.5 million for $140,000

Dave Oancea, aka Vegas Dave, is famous for his bet placed on Kansas City Royals back in 2015. Oancea predicted the team’s victory in the World Series. At the time, the KCR hadn’t claimed a victory in 30 years.

Steve Whiteley: £1.5 million for £2 

This modest 61-year-old heating engineer managed to win a Tote bet. Whiteley guessed six winners in a horse race — a result that even the biggest gamblers couldn’t predict.

Fred Craggs: £1 million for £0.5 

Craggs’ incredible win contradicts those who believe that betting more means winning more. He placed only a 50p bet on eight horse races for his 60th birthday.

All the horses in his accumulator bet had low chances of winning. It’s cases like these that boost the gambling winning statistics. Overcoming the low probability—2,000,000 to one—made Fred one of the luckiest winners ever.

James Adducci: $1.2 million for $85,000

Tiger Woods winning the 2019 Masters made James Adduci a rich man, but his investment wasn’t exactly small. This 39-year-old day trader from Wisconsin used his savings to bet on his favorite player.

The gain is far from the largest slot machine payout in history, but it’s the biggest payout in golf betting history.

Charles Barkley: $800,000 for $500,000 

This NBA professional is also a talented gambler. His biggest win was during the 2002 Super Bowl. Back then, he bet half a million and 14 points on New England Patriots. When they beat St. Louis Rams 20–17, he gained $800k.

Darren Yates: $765,800 for $86

It happened in 1996, amidst the era of the biggest gambling wins. Yates won about $765,800 on a sporting bet. He cashed in on Frankie Dettori’s seven consecutive wins at the Ascot Races. Dettori was Yates’ favorite jockey, so they celebrated the “magnificent seven” together.

Mick Gibbs: £500,000 for £0.30 

Gibbs is another accumulator-bet wiz. He made it big through future sports bets across Europe. Even the biggest Vegas winners can be envious of this roofer’s luck.

In 2001, he put a mini-bet of 30p with which he predicted the outcomes of as many as 15 different games. The odds of him winning were one in 1,666,666.

Phil Mickelson: $560,000 for $20,000 

Given his alleged $2 million debt, Mickelson is far from being the biggest blackjack winner or overall gambler. Nevertheless, this golfer has a neck for sporting bets.

Once, 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.

Vegas Dave: $200,000 for $20,000

One of the biggest winners in Vegas did it again. This time Vegas Dave bet on the Ultimate Fighting Championship (UFC 193). He predicted that Holly Holm would overthrow Ronda Rousey when the odds of this happening were 1 in 11.

Mick Gibbs: $218,600 for $3.50

This lucky Staffordshire roofer made another successful bet. In 1999, he predicted nine European football games winners, taking the odds of only one in 1,666,666.

Biggest Casino Winners in the History of Blackjack

Also called twenty-one, blackjack is a casino game that combines luck and strategy. There are many books on beating the odds of winning this game.

Moreover, blackjack has the highest number of cheating attempts. It’s one of the most popular games, but, surprisingly, the house’s edge is lower than 1%.

Kerry Packer: $40 million 

Kerry Packer took the biggest blackjack win in casino history. The Australian billionaire played eight tables waging over $250,000 in a single night. The Las Vegas revenue statistics show that this event boosted MGM Grand casino’s popularity.

Don Johnson: $15.1 million

Johnson won this hefty sum playing in three different casinos—Borgata, Caesars, and Tropicana.

This former corporate executive had been trying his luck for five consecutive months. One night, he won nearly $6 million. And although this is not the biggest casino win in history, it’s extremely high even for Atlantic City’s bustling gambling scene.

Ken Uston: $4.5 million

Uston used card counting to win in Las Vegas casinos for six consecutive years (1975–1981). In fact, he’s the one who invented it. Needless to say, it took a while for casinos to get the drift and protect themselves with a ban.

Dana White: $2 million

Bans are not uncommon for players who claimed the biggest casino wins. In 2014, Dana White, the UFC’s president, nearly got banned from the Palms Casino. This high-roller won $2 million over three months. Casinos dealt with this by limiting him to a maximum of $25,000 per hand.

“Shoeless” Joe: $1.5 million

This nickname describes a barefoot gambler, by all appearances homeless. This 80-year-old gambled his social security check of $400.

Though his gains are far from the most money won at a casino, the event left no-one even-hearted. The story continues to live on at the Treasure Island Hotel and Casino, in part because Joe’s lucky streak lasted for an incredible 96 hours before he started losing.

Ben Affleck: $800,000

The famous actor was caught card counting and got a lifetime ban from the Hard Rock’s blackjack tables. Still, Affleck won $800,000 before getting the label “advantage blackjack player.”

Although frequent in blackjack, there are no bans for the biggest win on a fruit machine and similar types of games.

Michael Geismar: $470,000

This hedge-fund manager won almost half a million during a 2012 business convention. His lucky streak stretched over six hours! These long lucky hours were enough to make him a celebrity in the Bellagio casino in Las Vegas.

Goksel Selay: $132,000 

The luckiest taxi driver in the UK, Selay (53), won a combined jackpot of $132,000. This was the combined jackpot of Genting Casino Westcliff and 35 other casinos. Goksel says he had dreamt of big money coming his way before he won.

Largest Casino Winnings

Anyone can play casino slots or a fruit machine, as the British call it. Plus, it’s fast, and in a turn of the handle, you find out if it’s your lucky day or not. Online Casino Slots account for, on average, 85% of the revenue.

Anonymous: $39.7 million

At the Excalibur Hotel & Casino, an anonymous software engineer became the luckiest slot machine winner in gambling history.

The man started with a modest sum of $100 but went home with almost $40 million—the biggest ever casino winning in the history of slot machine gambling.

Jon Heywood: $19 million

This 25-year-old soldier changed the world of online gambling statistics forever. He won the Mega Moolah jackpot 25 minutes after he opened an online casino account! The sum he won is about $19 million.

This event entered the official Guinness world record. It is the biggest slot machine win-win ever for an online player.

Amy Nishimura: $9 million

The 71-year-old Nishimura won 8.9 million in just three hours by hitting the Megabucks jackpot at Fremont. The funny bit is that she invested only $100 and had $40 to spare after she hit the jackpot.

John Tippin: $11.9 million

The then 50-year-old postal worker hit the Megabucks Jackpot in Hilton, Las Vegas. In 1996, Tippin took the biggest slot machine win ever recorded for $9. Like in the movies, he landed the millions on his last turn of the handle.

Anonymous Australian: $8 million

The win was made on a Dark Knight slot machine by an anonymous Australian who won about $8 million.

Elmer Sherwin: $4.6 million 

The 76-year-old WWII veteran Elmer Sherwin is another lucky Megabucks Jackpot winner. What’s incredible is that he won the same jackpot 16 years later, and it was worth $21 million at the time.

Biggest Roulette Winners of All Time

Roulette has a reputation for being a pure-chance casino game. Its wheel rolls in every state except California, where the game is played with cards.

The following “kings of the wheel” had their intuition tuned-up for gain. Moreover, all relevant casino statistics reveal that most of them won against incredible odds.

Moreover, seasoned players know that exceptional circumstances also influence the outcome. But for the past year, the casino’s ambiance didn’t play a part. Given the pandemic, most of the big casino wins in 2020 happened online.

Pedro Grendene Bartelle: $3.5 million

2017 was a lucky year for this Brazilian businessman. An all-in bet on Red 32 made him a millionaire. Thirty-five to one payout turned his $100,000-worth chips into $3.5 million.

Sir Phillip Green: $2 million 

This British media mogul hit it big in one of London’s most exclusive casinos—Les Ambassadeurs Club. Although this is not the most money ever won at a casino, it endangered this casino’s existence back in 2004.

Charles Wells: $2.2 million

This win dates back to 1981, and with all calculations done, Wells’s gain in today’s money is worth $13 million. He did actually “break the bank.” There’s even a song about this event entitled “The Man Who Broke the Bank at Monte Carlo,” sung by Charles Coborn.

Mike Ashley: $1.14 million

Mike Ashley, the owner of Newcastle United, won big by betting on Black 17 in 2008. The invested amount of $670,000 is almost the biggest bet ever placed in a casino. It was a so-called complete bet on everything related to Black 17—James Bond’s pick.

Chris Boyd: $440,000

Betting his savings on the luckiest number in roulette — 7 Red — paid off for Boyd in 1994. The programmer put $220,000 or his three-year savings on the table.

Joseph Jagger: $375,000

This resourceful player studied the roulette wheel in the Monte Carlo Casino in 1873. When he noticed that the wheel has a bias towards some numbers, he cashed in on it.

The sum may not be the biggest casino win ever, but in today’s money, it’s worth millions.

Ashley Revell: $270,000

Revell was 32 back in 2004 when he put his entire life’s savings on Red 7 at the Plaza Hotel and Casino. This single roulette spin could put him on the streets. Instead, he doubled it.

Sir Sean Connery: £27,000

It happened at the Casino de la Vallee in Saint-Vincent, Italy, in 1963. The famous actor beat the one in 50653 odds of winning on roulette and gained £27,000. He won the most improbable of the big casino wins — betting on 17 three times in a row!


What is the biggest bet ever won?

The sports betting statistics reveal that the most significant bet won is an astounding $2.5 million. The now-famous Dave Oancea, aka Vegas Dave, won the amount during the baseball World Series in 2015.

Dave bet on the Kansas City Royals, a team that hadn’t won the WS in 30 years. He placed the bet in week one and let it ride until the end, refusing to cashout on several occasions.

Who has won the most money gambling?

Kerry Packer, an Australian gambler and a billionaire, won $40 million in a single Las Vegas night in 1995. Not only did he break the blackjack record, but he did it for the second time in a row.

His lucky streak lasted only 40 minutes, but we wagered approximately $250,000. The record is still standing, worldwide and in the MGM Grand, where he won this fantastic sum.

Who is the biggest gambler of all time?

We could say it’s Edward Thorp, who also wrote a book on the subject called “Beat the Dealer.” He may not be the luckiest, but he’s one of the most passionate players.

So much so, he left his career as a math and physics teacher to become a professional gambler. Now he’s worth $800 million and is a member of the Blackjack Hall of Fame.

What is the largest slot jackpot ever won?

The biggest slot machine jackpot so far is an impressive $40 million, won by an anonymous player in 2003. The lucky 25-year-old identified himself as a software engineer from LA. He won the exact sum of $39,710,826.36 for an investment of only $100.

What’s the most money ever won at a casino?

Kerry Packer’s $20–$40 million in MGM Grand in 1995 is the largest sum won at a casino so far. That night Packer invested $250,000.00 on eight different blackjack hands to reach it.

A strong second is the $39.7 million from a slot machine in Excalibur casino made by an anonymous 25-year-old.

Which casino has the most winners?

The MGM Grand has the luckiest casino status ever since it hosted the biggest ever win in 1994. Then, Kerry Packer won somewhere between $20–$40 million in a single night.

Opened in 1993, it remains one of the largest casinos in the world today. Actually, it’s the 9th-biggest casino on the Las Vegas Strip.

When going in for the win, choosing a lucky casino is as important as wearing your lucky clothes. It’s worth knowing that the MGM Grand has counted the biggest gambling wins for almost three decades now.

Bottom Line 

Gambling is a principle inherent in human nature. But the majority dream of “breaking the bank.” Still, not every winner on our list has the “greedy gene.” In fact, some of the wins were pure accidents.

However, it’s lucky coincidences like these that keep gamblers trying. These success stories will remind you that lady luck may be hiding just around the corner.

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