Astonishing Live Casino Wins You Won’t Believe

While online casinos have awarded some considerable jackpots to players since they first rolled onto the scene in the late 1990s, their live-action counterparts are very much ahead of the game. Believe it or not, all of the most significant prizes ever awarded come from a brick-and-mortar venue, and have come from games including slots, blackjack, poker and roulette. 

The names of the lucky winners and what they spent their prize on, however, are not always publicly known, but the sheer size of the winnings definitely are. Believe us, there are some genuinely eye-watering sums you will not want to miss. Read on, chums.

The Three Biggest Slots Wins Ever

In both an online and live setting, one game has the title of offering the biggest jackpots out there: slots. Progressive slots, in particular, can have prize pools well into the millions. How? Well, these games are linked in a network, and a small percentage of every spin of the reels is fed into a running jackpot. This process only stops when it's triggered and won.  

Biggest Jackpot of All Time

As of 2024, the single largest jackpot ever awarded to a casino player is a whopping $39.7 million over 20 years ago back in 2003! According to a CPI inflation calculator, this prize is worth roughly $66 million in 2024's purchasing power. It's been reported the winner was a 25-year-old software engineer from Los Angeles who visited the Excalibur Hotel & Casino in Las Vegas for a quick hit of the Megabucks slot machine. Other than that, little is known about the winner. Their name isn't public knowledge or what the person did with their massive prize. Nobody has ever topped this win in the two decades since this anonymous player won. 

Second Biggest Slots Jackpot Ever

Coming in second place with a $34.9 million jackpot is Cynthia Jay-Brennan, possibly the luckiest and unluckiest person to ever win a prize at the casino. While working as a Las Vegas casino waitress in 2000, Brennan would occasionally have a few spins on the slots. Most of the time, she walked away empty-handed. However, that all changed while she was at the Desert Inn Hotel and Casino celebrating her boyfriend's mother's birthday.

Following the meal, she decided to have a few spins on the Megabucks slot machine, playing with $27; she had her first two spins, nothing of note happened. Then, on the third spin, the machine erupted in light and three flashing symbols; she had won the jackpot. And not just any jackpot mind you, one of the largest ever at the time: a staggering $34.9 million. Surprisingly, she still went to work the next day and gave her employer two weeks' notice, even offering to train her replacement.

What about that unlucky part, we mentioned? Well, for a few months, Brennan's life changed greatly for sure; by all accounts, she was happy to share her prize with whoever needed it. She was delighted to provide financial support for old friends, family, and pretty much anyone who reached out with a story of woe. She also got married and went on a holiday. Everything was looking up. Sadly, her life changed again in March, and this time, not for the better.  

Brennan was travelling in a car with her sister, and a drunk driver struck them. Her sister died, and Brennan was left paralyzed from the waist down. For a time, she was in a coma. To this day, she is still in a wheelchair and, barring a miracle, is unlikely to ever walk again.  Despite the tragedy, Brennan has still made sure to spend her life and considerable wealth helping others through grand acts of charity, such as donating wheelchairs to patients in similar situations to hers.

Another Anonymous Player Takes Home a Fortune

The third biggest slots jackpot ever was won by a retired flight attendant who took home $27.6 million playing the Megabucks slot machine at the Palace Station Casino in Las Vegas around 1998. Like many of her fellow winners, she decided to keep her name out of the public eye. Very little is known beyond her profession and the size of the prize. Reports indicate she spent roughly $300 before hitting the jackpot.

Three of Blackjack's Biggest Winners

It's a game known by a few different names: 21, pontoon and, of course, blackjack. Often characterized as the perfect blend of luck and skill, blackjack has the potential to award some huge prizes to lucky players as the following three men discovered. 

The Legend of the Media Mogul

During his lifetime, Australian media tycoon Kerry Packer was a frequent sight at blackjack tables all over the world. The stories about his losing streaks, and more importantly, his winning streaks, are legendary. He apparently won and lost a fortune playing blackjack over the years. One story of note claims he won quite possibly the largest prize ever awarded in blackjack. 

Depending on which version of the tale you read, in the 1990s, Packer was playing at a casino in Las Vegas. Which casino and the exact date differ, as does the amount won. Depending on who tells the story, over the course of 40 minutes across eight tables, Packer won between $20 and $40 million, playing $250,000 a hand. If true he would likely have the record for the biggest win at the blackjack tables ever. Few people could afford such high stakes to replicate the feat. 

Lowering the House Edge Works Wonders

Don Johnson spent a great deal of his early years around the horse racing industry. At various points, he was the manager of a racetrack, a state regulator of the horse racing industry, and even founded a company that creates computer programs to help predict the winner of horse races. Away from the racetrack, it turns out Johnson was also a top-notch blackjack player who won over $15 million in late 2011/early 2012, with one of his biggest winning streaks netting him over $6 million in one night.

Following the 2008 financial crisis, it was a grim time for many businesses. Consumers were strapped for cash and the economy was in turmoil. Casinos were also in dire straits and had begun offering favorable terms to entice high rollers to visit. In 2011, Johnson took up the offer and played blackjack with some very favorable terms that are almost too good to be true. 

Johnson asked for rules such as six decks, a maximum table play amount of $100,000, and a 20% loss rebate that would reset every day, to name just a few of the stipulations. Overall, he estimated with his desired rules and playing strategy, the house edge was lowered to less than 1%. Generally, the house edge for blackjack is over 2%. Casinos must have been desperate because at least three agreed. Under these terms, Johnson was able to win nearly $6 million playing blackjack in one night in Atlantic City's Tropicana Casino. 

He also managed to win around $5 million from the Borgata and at least $4 million from Caesars. According to Johnson, he won $800,000 in one hand, while another three-hand sequence scored him $1.2 million. Needless to say, the reason he only took home $15 million was because the casinos eventually refused to continue offering Johnson the rules he had asked for, instead reverting back to the standard set. At this point, it appears Johnson quit while he was ahead and just stopped playing.

The Card Counters

The MIT blackjack team is notorious and arguably the most famous card counters in casino history. Formed around 1979 by students from MIT, Harvard, and other prestigious institutions, the team used card counting and other acts of subterfuge to win millions from unsuspecting casinos. 
Operating until the early 2000s, the team had dozens of members during the years it operated. No one knows for sure how much the team won over the decades, except maybe the team members themselves. The few who have spoken publicly are very careful not to disclose the actual sum. However, estimates range from $5 million to nearly $100 million. Either way, it's a significant prize to win from blackjack, even if it is split between many people. 

Poker 

Poker is a rare game at the casino. The player's skill plays a huge factor in success or failure. A few lucky pros managed to leverage their skills to take home a prize far bigger than some people receive after an entire lifetime of playing poker.

Making Millions for Charity

All the most significant prizes for poker came from one tournament, the Big One for One Drop. The game is an invitation-only, multi-day no limit Texas Hold 'em tournament hosted as part of the World Series of Poker (WSOP) circuit in the United States. Founder Guy Laliberté created the tournament in conjunction with the One Drop Foundation, an initiative focussed on providing permanent safe water to people in crisis areas. The charity receives contributions from the poker tournament prize pool.

Since the first event in 2012, the buy-in has ranged from $111,111 up to $1 million, creating some of the largest prize pools in poker history. In its first year, poker pro Antonio Esfandiari won a staggering $18.3 million after beating 48 others who entered the tourney. To date, it's still the largest ever single prize won in a poker game, both live and online. 

In second place for the biggest poker win ever is poker pro Dan Colman, who won the 2014 event, taking home $15.3 million for his efforts. Elton Tsang has the third largest prize ever won in poker, with just around $12.2 million from winning the second Big One for One Drop event held in 2016. Fedor Holz won the other 2016 event but didn't even get close to matching Tsang's prize. American Daniel Weinman came close to bumping Tsang out of the top three when he won the 2023 WSOP Main event, taking home $12.1 million.

Roulette

A game that involves pure luck, roulette has still managed to award some huge prizes to players over the years. Nobody knows where the ball will land after the wheel stops spinning, but it certainly gets the adrenaline pumping trying to guess. It’s hard to know who has the biggest wins from playing roulette because it’s not a competition that receives media coverage like poker, however, there have been several big wins that made it into the public eye. 

A British Media Mogul Nearly Shutters a Casino

One of the wealthiest men in the United Kingdom, British billionaire and media mogul Sir Philip Green, apparently nearly forced the Les Ambassadeur's Casino in London out of business after a massive win at the roulette table. Back in 2004, the media mogul played $680,000 on a single spin and managed to walk away with $3.6 million. A hefty sum at the best of times, apparently the casino was very concerned about its finances in the aftermath and had to start enforcing table limits.

Nephew of Brazilian Businessman Goes All in on Red 32

Roulette is fast, nerve wracking and often heartbreaking when your number doesn't come up. However, that only makes it all the sweeter when you do win; just ask Pedro Grendene Bartelle, a man who turned roughly $100,000 into $3.5 million by putting it all on red 32.
In 2017, at Uruguay's Hotel Conrad in Punta del Este, Bartelle took the chance of playing it all on one number, which has roughly 1 in 38 odds of success. It certainly paid off though; there is even a video online showing the moment he won, and it's everything you'd expect. Pedro, who is the nephew of famous Brazilian billionaire Alexandre Grendene Bartelle, won what could possibly be one of the biggest prizes from roulette ever.

The Old Conman

Charles Wells was a well-known conman and career criminal when he won around $2 million on a spin of roulette back in 1892 at the Monte Carlo. Wells spent his time working as a thief and conman in London during the 1860s. After spending some time in jail, he decided a move to France was on the cards. One night he ended up at the famous Monte Carlo casino, which had only opened 27 years earlier in July of 1865.

Wells was a known casino cheat and had multiple aliases he used while conducting his scams, so if he ever got caught, he just changed his name and went to another casino. It turns out it was much easier to scam a casino before the invention of CCTV and other electric cheating countermeasures. 

Despite his dubious background, and newspapers dismissing his wins as a publicity stunt, the casino claimed Wells's win was legitimate. He was allowed to walk away with his roughly $2 million in winnings, which would be worth about $13 million in 2024. There's even a song about this event entitled "The Man Who Broke the Bank at Monte Carlo," sung by Charles Coborn.