17 Gamblers Who Got Rich

By in Casino & Gaming on
Man Counting Money

Have you ever dreamed of going on a gambling hot streak and winning a fortune?

I know I have.

Unfortunately, I also know that the odds are heavily skewed against it ever happening.

But there are gamblers who’ve seen their dreams come true, either through luck or skill. And in some cases, these players have won millions of dollars!

Below you can see a list of 17 gamblers who won enormous sums of money from the casino.

But the only catch is that their feats will never be repeated!

1. Don Johnson – Blackjack Dealmaker

How Don Johnson Won $15 Million Playing Blackjack

Up until 2011, Don Johnson was synonymous with the Miami Vice actor.

But this changed when Don Johnson the gambler made a killing in blackjack games.

Johnson has extensive experience in the gambling world, working as a state gaming regulator, developing horseracing software, and managing Parx Casino and Racing.

His various roles gave him the math skills and casino knowhow to become a blackjack expert.

In 2010, Johnson was contacted by several Atlantic City casinos, who mistakenly identified him as an unskilled blackjack player based on his previous visits.

Johnson used this false image to his advantage by negotiating for more favorable rules.

Some of these rules included:

  • 20% loss rebate on losses exceeding $500,000.
  • Dealer standing on a soft 17.
  • Re-splitting aces.
  • 3:2 natural blackjack payouts
  • Free bet if the dealer makes a mistake

The loss rebate is the big thing because Johnson was able to get a 20% refund if he had a bad session (although he never needed it).

The free bet for dealer mistakes is the second big factor. This led Johnson to forming an entourage with friends and hired porn stars, where they created a distracting party atmosphere used to throw the dealer off.

Based on the rules he negotiated for, combined with the free bets, Johnson won $15 million from 2010-11. This included a $6 million win against Tropicana, which resulted in their CEO being fired for okaying the favorable rules.

Why Johnson’s Feat will Never be Matched

Johnson caught Atlantic City at a desperate time, where they lost a large number of visitors due to the Great American Recession. This made casinos more willing to negotiate with Johnson on favorable rules that they might not otherwise allow.

But following Johnson’s hit job, which made him a minor celebrity, casinos from Vegas to Atlantic City are more careful with their high stakes negotiations.

2. Billy Walters – Roulette Wheel Bias Master

How Billy Walters Won $3.8 Million Playing Roulette

Billy Walters is a great all-around gambler, having won millions of dollars through both golf and sports betting. Showing that he’s truly a gambling stud, Walters also won $3.8 million in roulette.

In 1986, Walters and his professional gambling team visited Atlantic City’s Golden Nugget Casino.

Their plan was to record results from various wheels in order to find if any wheels favored certain numbers (a.k.a. wheel bias). They got the information they were looking for, and used this knowledge to place wagers involving the biased numbers/sections.

By the time the Golden Nugget realized that Walters’ team wasn’t going to lose, they banned the group. But not before losing almost $4 million.

Why Walters’ Feat Will Never be Matched

Walters won his fortune by spotting biased numbers on imperfect wooden wheels.

The problem with wooden wheels is that they’re more susceptible to wear and tear. When this happens, advantage players have a chance to win long-term profits by recording enough results to find statistical bias.

Following Walters’ win, casinos began installing low-profile wheels (shallow pockets) to keep roulette wheels from wearing down and favoring certain numbers.

Since then, the Starburst Wheel – which features sturdy, metal number dividers – has been even more important with regard to halting wheel bias.

3. Phil Ivey – Online Poker Domination

How Phil Ivey Won $19 Million Playing Online Poker

A Poker Hall of Fame member, Phil Ivey proved he belongs by crushing high stakes online poker games from the mid-2000s to early 2010s.

According to his stats at HighStakesDB.com, Ivey booked the following online cash game profits:

  • 2007 – $1.99 million
  • 2008 – $7.34 million
  • 2009 – $6.33 million
  • 2010 – $3 million

Aside from winning almost $19 million through internet poker, Ivey has earned a fortune in live cash games and tournaments ($23.87 million).

But following Black Friday – when the world’s largest poker sites stopped serving US players – Ivey slowed down his internet poker play and now focuses more time on business pursuits.

As we’ll cover later, he also became an advantage baccarat player who won millions from casinos.

Why Ivey’s Feat will Never be Matched

Ever since Black Friday, the online poker industry has been in a steady decline.

A big reason for this is because the largest sites no longer serve American customers. Another problem is that skill-based players have more options these days like daily fantasy sports, Esports, and Hearthstone.

With the online poker industry in decline, nobody makes $6-$7 million a year anymore. That said, don’t expect an internet player to win as much as Ivey.

4. MIT Blackjack Team – Card Counting Corporation

How the MIT Blackjack Team Won Millions through Card Counting

Formed by students from the Massachusetts Institute of Technology, Harvard University, and Harvard Business School, the MIT Blackjack Team was a well-organized group of blackjack card counters who dominated casinos.

They especially became famous through the 2008 film 21.

Card counting was nothing new when the MIT Blackjack Team formed. In fact, Edward Thorp was counting cards in the early 1960s.

But what made the MIT Blackjack Team special is that they worked like a corporation, drawing investments and using these to fund teams and casino trips across the world.

A testament to the group’s success is how they lasted from 1979 until the early 2000s.

Why the MIT Blackjack Team’s Feat will Never be Matched

Every time an individual or group burns casinos, they make efforts to curb or eliminate advantage play in the aftermath.

Of course, the MIT Blackjack Team was so skilled that they burned casinos for tens of millions of dollars.

Over the decades, casinos have become very adept at catching counters and banning them from casinos. This means you won’t ever see anything to the degree of the MIT Blackjack Team again.

5. Patricia Demauro – Dice-Rolling Granny

How Patricia Demauro Won $180,000 Playing Craps

Patricia Demauro, a New Jersey grandmother, is the unlikeliest of people to go on an incredible gambling streak. In fact, her notable gambling story came on her second-ever time playing craps.

Demauro went to the Borgata Hotel & Casino with her friend, John Capra. The pair ended up playing craps together, and Demauro eventually got her chance to roll the dice.

What ensued next was a 4-hour dice-rolling clinic, where Demauro rolled 154 straight times without sevening out. This is officially recognized as the longest craps-rolling streak in world history.

While Demauro declined to say how much money she won, I’ve seen estimates of $180,000.

Why Demauro’s Feat will Never be Matched

What are the odds of rolling dice 154 times without a seven coming up?

According to Time, the odds are roughly 1 in 1.56 trillion.

Maybe somebody will roll more times than Demauro. But I wouldn’t bet on it happening any time soon.

6. Kelly Sun & Phil Ivey – Beating Baccarat with Edge Sorting

How Kelly Sun and Phil Ivey Won $21.6 Million Playing Punto Banco

A wealthy Chinese socialite, Cheung Yin Sun (a.k.a. Kelly Sun) lost most of her fortune through gambling. It was at this point that she set out to beat casinos, studying card decks so she could spot imperfections (a.k.a. edge sorting).

Sun eventually found that a purple Gemaco deck had tiny flaws that could be spotted with a trained eye. She then used this information to predict what card values would come up before they were flipped over.

In 2012, Sun worked out a partnership with Ivey, whereby they’d use Ivey’s large bankroll and Sun’s edge sorting knowledge.

The pair made $12 million at Crockfords Casino, and another $9.6 million at the Borgata while playing punto banco (baccarat variant).

While the Borgata paid Ivey, Crockfords refused pay out, citing a bank holiday. The London casino then investigated the matter and decided not to pay Ivey at all.

Ivey launched a lawsuit against Crockfords to claim his winnings and lost. He was then sued by the Borgata for $9.6 million and lost this case as well.

He’s currently in the process of appealing both decisions.

Why Sun and Ivey’s Feat will Never be Matched

Ivey and Sun relied on a flawed deck, which is hard to find without investing a considerable amount of time.

And based on the fact that Ivey and Sun haven’t been able to collect on their winnings, we doubt anybody will try to emulate their feats.

7. Keith Taft – Inspector Gadget Beats Blackjack

How Keith Taft Won Hundreds of Thousands (Legally) Cheating Blackjack

Keith Taft was inspired by Edward Thorp’s card counting book, Beat the Dealer. But Taft had no luck in becoming a card counter himself.

That said, he turned to his real skill – electronics and computing – to create computer devices that helped card counters beat the casino.

Taft himself won $40,000 the first time that he used a computer called David. He then began selling the gadget to interested players for $10,000.

Along with his son, Marty, Keith made another device called the “Belly Telly,” which, when placed in one’s belt buckle, reveals the dealer’s hole card.

By 1985, Nevada regulators made it a felony to cheat casinos with electronic devices. But Taft had already made hundreds of thousands of dollars and retired by this point.

Why Taft’s Feat will Never be Matched

I don’t suspect that criminals will stop using electronics to cheat casinos in the future.

But the days of computer geniuses like Taft legally winning gambling profits with James Bond-like devices are long over.

Every major gambling destination will prosecute you for doing anything close to Taft’s feat.

8. Antonio Esfandiari – Winner of $18.3 Million Poker Payout

How Antonio Esfandiari Won an $18.34 Million Poker Payout

Antonio “The Magician” Esfandiari has a long poker career dating back to the early 2000s. But none of his accomplishments are as notable as winning the 2012 WSOP Big One for One Drop along with $18,346,673.

The Big One for One Drop’s $1 million buy-in helped Esfandiari win this incredible sum.

A combined of 48 poker players and businessmen ponied up the record-poker tournament buy-in. And Esfandiari beat Sam Trickett ($10.1 million) heads up to win the event.

Why Esfandiari’s Feat will Never be Matched

While live poker remains popular, the days of $1 million buy-in tourneys appear to be over.

In fact, the World Series of Poker is featuring more tournaments with buy-ins from $500-$2,500 than ever before. And their current largest buy-in is $111,111 for the One Drop High Roller.

Looking at the current trends, Esfandiari’s $18.34 million payout will likely never be topped.

9. Joseph Jagger – The Original Roulette Wheel Bias Genius

How Joseph Jagger Won £120,000 (£12 Million) Playing Roulette

In the 1870s, Joseph Jagger used his engineering background to deduce that with enough wear and tear, roulette wheels will favor certain numbers.

The Englishman put this theory to the test by hiring clerks to visit Monte Carlo and record roulette results. When they returned with the data, Jagger used this info to find out which numbers the wheels favored.

He found one wheel in particular that was biased towards several numbers, then he left for Monte Carlo.

In the 1901 book, Monte Carlo Anecdotes and Systems of Play, author Victor Bethell claimed that Jagger won £120,000 (£12 million) through wheel bias.

Why Jagger’s Feat will Never be Matched

It’s beyond me why casinos didn’t make more of an effort to change wooden roulette wheels after Jagger won a fortune through wheel bias.

Whatever the case may be, it allowed Walters and Gonzalo García Pelayo (discussed later) to also profit from wheel bias.

10. Tobey Maguire – Crushing Underground Celebrity Poker Games

How Tobey Maguire Won $40 Million Playing Poker

Known for his roles in the Spiderman trilogy and other films, Tobey Maguire has made a fortune from acting. But he padded his bank account even more in 2011 through underground celebrity poker games.

Hosted by the infamous Molly Bloom – author of Molly’s Game – these games featured major celebrities, including Alex Rodriguez, Ben Affleck, Dan Bilzerian, Leonardo DiCaprio, and Matt Damon.

The ring was blown wide open after hedge fund manager Brad Ruderman lost $25 million worth of his clients’ money. Ruderman’s former clients sued Maguire and other players to recoup some of their losses.

According to the Daily Mail, Maguire won an estimated $40 million through the poker action.

Why Maguire’s Feat will Never be Matched

For one thing, we’re not in the poker boom any longer, and it’s unlikely that underground games will reach these stakes again.

Another reason is that the odds of this much star power getting together for a high stakes poker game again are slim.

Throw in the fact that Maguire must be a rare breed to excel in both poker and acting, and it’s unlikely that another star will bank this much in poker again.

11. Gonzalo García Pelayo – Tracking Roulette Numbers with His Family

How Gonzalo García Pelayo Won $3 Million Playing Roulette

Pelayo is a jack of all trades, having worked as a film director, music producer, radio announcer, and television presenter. But what he’s best known for is beating casinos out of a fortune.

The Spaniard recruited his son, Iván, and they recorded results from different roulette wheels in Casino Gran Madrid. He then entered the information in a computer to see what numbers the wheels favored.

Pelayo discovered biased numbers on one wheel, and he used this information to win approximately $1.5 million.

Casino Gran Madrid banned him afterward, leading Pelayo to use the same advantage-play method in Las Vegas. He won another $1.5 million, running his grand total up to $3 million.

Why Pelayo Feat will Never be Matched

See the Billy Walters’ section in point #2.

12. Archie Karas – Greatest Gambling Streak Ever

How Karas Won $40 Million Playing Casino Games

Archie Karas claims to have gambled the most money in casino history. And based on his incredible gambling streak, I wouldn’t be surprised.

The story of Karas’ legendary run began after he lost all but $50 playing high stakes poker. Rather than trying to slowly rebuild his bankroll, the Greek-born gambler left L.A. for Las Vegas.

“You’ve got to understand something,” Karas once said.“Money means nothing to me. I don’t value it. I’ve had all the material things I could ever want. Everything. The things I want, money can’t buy: health, freedom, love, happiness.”

Karas used this philosophy in 1993, when he turned a $10,000 loan into $7 million through a combination of pool and poker.

Feeling his hot streak, Karas took on elite poker players like Doyle Brunson, Johnny Chan, Johnny Moss, Puggy Pearson, and Stu Ungar. Karas won millions against these pros, citing Brunson as the only player to beat him.

Armed with $17 million, Karas couldn’t get any action in poker or pool, so he turned to craps. Despite playing a house-banked game, he ran his bankroll up to $40 million through craps games at Binoin’s Gambling Hall.

The streak would finally come to an end in 1995, when Karas lost the following amounts in order:

  • $11 million in craps.
  • $2 million in poker to Reese.
  • $17 million in baccarat.
  • $10 million in craps and baccarat.

Amazingly, Karas would go on another run in 1995, where he turned $40,000 into $5 million. But he lost the entire amount in a single day.

Why Karas’ Feat will Never be Matched

Karas is often cited as turning $50 into $40 million, which isn’t true because he started gambling with a $10k loan.

Nevertheless, he got a 4,000-to-1 return on his investment when his bankroll reached $40 million.

The odds of anybody replicating this type of run are slim to none. And the fact that Karas turned $40k into $5 million just a year later is mind-boggling.

13. Aaron Jones – Biggest Ever Daily Fantasy Sports Champ

How Aaron Jones Won $5 Million Playing Daily Fantasy Sports

Before entering the daily fantasy sports (DFS), Aaron “aejones” Jones was a successful live and online poker player. He also bought a poker training site called LeggoPoker, then sold it to Ivey four years later.

But Jones – an Indianapolis native – would eventually tire of spending half the year in Toronto and Mexico just so he could play at the largest online poker sites (due to Black Friday).

By 2014, he had transitioned all of his time towards DFS.

This turned out to be a great decision because Jones won $5 million in the 2016 DraftKings $15 Million Fantasy Football World Championship.

The contest featured 14 weeks’ worth of qualifiers during the NFL season. The top 200 points earners advanced to the final round in Las Vegas, with a $5 million top prize on the line.

Jones, who was sitting in fifth place during the final day, got big performances from Arizona’s Larry Fitzgerald and Pittsburgh’s Martavis Bryan to win.

Why Jones’ Feat will Never be Matched

DraftKings $15 million football championship came in January 2016 – the pinnacle of daily fantasy sports.

But months afterward, industry leaders DraftKings and FanDuel became locked in bitter lawsuits over DFS’ legality.

Many states like New York settled with the two DFS giants and legalized and regulated their markets. But prior to 2016, DFS sites were free to offer services to any state without regulation, licensing fees, and heavy taxation.

For these reasons, I don’t ever see a DFS company offering a prize as big as $5 million again.

14. Peter Edwards – Betting on His Grandson’s Football Future

How Peter Edwards Won £125,000 on His Son Making the Welsh National Football Team

A big football fanatic, Peter Edwards had a strong belief that his grandson, Harry Wilson, would one day play on the Welsh National Football Team.

Edwards approached a William Hill betting about the matter, and laid £50 on Harry achieving this goal.

Given that Edwards was just three years old at the time, this was a long shot. And the Wrexham, England-based betting exchange gave him 2,500-to-1 odds on the wager.

Just 13 years later, Edwards’ bet came through when Harry played in a World Cup Qualifier. Appearing in Wales’ 2013 match against Belgium at age 16, Harry is the youngest player to ever represent the Welsh National Team.

Perhaps just as impressive is that Edwards won £125,000 ($200,000) for the bet.

Why Edwards’ Feat will Never be Matched

Wales has a population of 3 million, and national football teams carry 23 players on their roster.

Doing the math (3,000,000 / 23), this means that Harry Wilson had 130,434-to-1 odds of playing for the Welsh National Team at any time.

Of course, players rotate on and off national teams all the time. And many of Wales’ 3 million people wouldn’t be the proper age or physical condition to play professional football.

But even if we include these factors, it’s still a long shot for somebody to make a national football team roster – especially in a football-crazed nation like Wales.

Maybe someone will pull of another bet like this again in a smaller country. But it’s hard to see them winning as much money as Edwards did.

15. Charlie Wells – The Man who Broke the Bank at Monte Carlo

How Charlie Wells Won £6 million Playing Roulette

Charlie Wells started his adult life honestly, investing and selling a device that regulated the speed of ship propellers. But then he used his invention knowledge to start conning people out of their money.

His most-notable con was a musical jump rope – an idea that netted him £4,000 (approx. £400k today) in investments.

Rather than putting this money towards developing the fictional invention, he traveled to Monte Carlo and started playing roulette. What ensued is one of the greatest roulette runs in history.

Over the course of two visits, he turned his £4,000 stake into £60,000 (£6 million). During one of the visits, Wells broke the bank (win every chip at a table) 12 times, and won five consecutive bets on the number 5 (36:1 odds).

Following his second successful gambling trip, Wells became celebrity in England. He even inspired the famed British song The Man Who Broke the Bank at Monte Carlo.

Wells would return to Monte Carlo a third time, traveling on a giant custom yacht that he purchased. This visit would be his undoing as Wells lost the rest of his fortune on the Monte Carlo roulette tables.

His life would only get worse when he was convicted of fraud in 1993 and sentenced to eight years in prison.

Why Wells’ Feat will Never be Matched

The casino hired investigators on suspicion that Wells was either cheating or using an advantage play method.

They couldn’t find anything because Wells was simply using the Martingale system – where you double bets after every loss to recoup winnings.

In theory, the Martingale system works because you can always win back losses at some point. But the downside is that you’ll eventually lose/double bets so many times that you’ll lose your bankroll (or reach the table limit).

Wells is incredibly lucky that he was able to amass a fortune on his first two visits. Based on the luck factor and modern-day table limits, nobody is likely to win this much with the Martingale again.

16. Sean Connery – Bond Wins Big in Italy

How Sean Connery Won £163,000 Playing Roulette

A little-known fact about famed Scottish actor Sean Connery is that he began gambling when he was a kid. And this gambling itch served him well during a 1963 casino trip to the Italian Alps.

Connery’s lucky number must be 17 because he kept placing his money on this single-number wager. The former James Bond missed his first few bets, but then started winning.

Each time Connery won, he would leave his 35:1 payout on the table and bet on 17 again. In the end, he won three straight times, resulting in a £163,000 profit.

What’s interesting is that Conner’s Bond character would hit the same number while playing roulette in the 1971 film Diamonds are Forever.

Why Connery’s Feat will Never be Matched

The odds of somebody winning the same single-number wager three times in a row aren’t impossible. After all, Charlie Wells won a single-number bet five times in a row.

But the odds of somebody pulling off this feat and being as famous as Connery are astronomical.

17. Anonymous Software Engineer – Biggest Slots Jackpot Ever

How a Software Engineer Won $39.7 Million Playing Slots

In 2003, an anonymous software engineer from L.A. visited Las Vegas’ Excalibur casino.

The 25-year-old was in Vegas to watch and bet on NCAA March Madness basketball games. While there, he started playing the famed Megabucks progressive slot machine.

Just a short time later, he hit a jackpot worth $39,710,826. This remains the largest slots win in history.

Given the fortune that the young man won, it’s no wonder why he chose to keep his identity hidden from beggars and distant relatively looking for some generosity.

Why Their Feat will Never be Matched

First off, no slots payout has come close to matching this amount since 2003. And a big reason why is because fewer and fewer people are gambling in Las Vegas these days.

Online slots jackpots have gotten larger over time. In fact, Britain’s Jon Heywood won a slots payout worth €17,879,645 ($20,062,600) in 2015.

But this is still only halfway to $39.7 million.

Conclusion

These 17 players show that it’s not impossible to get rich through casino games.

Of course, given that casinos have closed many of the loopholes that aided these gamblers, winning a casino fortune isn’t easy either.

Card counting is still a legitimate advantage play method, while poker and daily fantasy sports can be beaten with skill.

As for winning with craps, punto banco, roulette, and slots, you’re at Lady Luck’s mercy.

Nevertheless, it’s always fun to dream big when you play casino games. And you can guarantee that players are out there right now finding new advantages to make these dreams come true.

Michael Stevens

Michael Stevens has been researching and writing topics involving the gambling industry for well over a decade now and is considered an expert on all things casino and sports betting. Michael has been writing for GamblingSites.org since early 2016. ...

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