In no particular order, here are some of the most legendary gamblers ever!
12 - Charles Barkley Former NBA all-star Charles Barkley lost a
lot of money at the casino.
At one point, he admitted that he probably had a small gambling, let’s call it, “problem”.
Thankfully though, Sir Charles was making a lot of money playing in the NBA.
So as long as he didn’t bet too much money, he felt that he was fine.
But that doesn’t mean he didn’t lose a ton of cash while gambling.
In an interview with ESPN in 2006, Barkley admitted to having lost somewhere around $10
million dollars over his entire gambling career.
Again, he didn’t think it was anything serious since he could afford to lose a few million
dollars every now and then.
And that was only for the money he’s lost since 2006.
In 2008, he quit gambling momentarily for two years, something that really helped out
his gambling habit.
Barkley hasn’t completely stopped gambling.
But when he resumed, his mindset changed quite a bit.
At that time, he swore to gamble in quote “moderation”, and he stopped when he lost
$200 grand.
But did he really keep that promise to himself?
Barkley was open about his habits with Seth Davis during an interview.
Davis had asked Barkley just how bad his gambling has gotten since his 2 year hiatus from gambling.
And this is when Barkley confessed that he had probably lost a million dollars on 30
separate occasions for a total gambling loss somewhere near 30 million dollars!
11 - Andy Beal The distinction of biggest poker player ever
could belong to Andy Beal.
He’s a businessman who’s made a big fortune in real estate and banking.
As of 2021, Forbes places his net worth at roughly $7.9 billion making him one of the
wealthiest individuals in the world.
He first ventured into business in high school by repairing and reselling broken TV sets.
He later moved on to making his big money starting in real estate.
It was the same business model.
He made a few fixes here and there on properties and then he sold them for a big profit.
These early business ventures, according to some reports, might have been funded by Beal's
poker winnings in college.
While that’s mostly speculation, his gambling in the 2000s are well-known and well documented.
Starting in 2001, he started going to Las Vegas to play against some of the best poker
players at the time in the biggest games.
The professional players were collectively referred to as The Corporation.
It consisted of pros such as Ted Forrest, Todd Brunson, Jennifer Herman, and eventually,
the legendary Phil Ivey.
They had pooled their bankrolls together to share the risk and play against Andy.
Andy himself proved to be a capable player.
For example, in 2004, he won a staggering $11.7 million dollar pot from The Corporation,
which was the biggest known pot in the history of poker at the time.
But he was playing the best in the world, so in the long run, he was going to lose.
Beal would ultimately lose $16 million dollars to the Corporation total and he made a vow
to never to play against them again.
However, Beal was back again in February of 2006 to face off with The Corporation again.
Andy beat the pros at first for $13.6 million dollars over the course of three days.
But just like the first time, things weren’t going to go well for him.
This is when The Corporation decided to have Phil Ivey go up against Beal.
Ivey went on to beat Beal for $16.6 million dollars in just three days.
After that embarrassment, Beal never played against the corporation again.
In 2011, there were reports that he had lost over $50 million dollars total in some underground
poker games in less than three days.
If those reports are true, then Beal is known to have lost roughly 70 million dollars lifetime
in poker alone!
10 - Haralabos Voulgaris Haralabos, or simply Bob, is considered to
be one of the biggest sports bettors around.
His betting focuses mainly on the NBA.
He also dabbled in poker but basketball has been his ultimate profit generator.
His dad had a lot to do with that.
At 18, Voulgaris frequented Caesar’s Palace casino with his dad.
But since he wasn’t of legal age to be at the tables, he spent his time watching NBA
games in the sportsbook.
There at the casino, he placed his first bet ever, which he lost.
But he got hooked anyways and he would go on to place wagers on NFL and CFL games throughout
college at the University of Manitoba.
By the time he graduated, Voulgaris was so good at his craft that he had a sizable chunk
of cash which just meant more gambling for him after school.
After he graduated, he focused his betting on the coaching strategies of three main coaches.
Byron Scott of the New Jersey Nets, Eddie Jordan of the Washington Wizards, and Jerry
Sloan of the Utah Jazz.
Aside from that, he also noticed a major flaw in how the casinos treated individual halves
of a game.
Basically, they didn’t account for the increased likelihood of scoring in the 4th quarter,
something that Voulgaris capitalized on.
At the height of his gambling career, supposedly he was betting a million dollars daily.
With his winning rate of nearly 70%, Vulgaris was simply crushing casinos.
But the situation changed once the bookmakers realized their mistake and winning for Voulgaris
became harder.
In 2005, he worked with a math genius known simply as “The Whiz” to create a projection
system called Ewing.
The Whiz finally completed Ewing in 2008.
It was an okay system although Bob said its accuracy kept on dwindling over time so he
had to significantly increase his betting amount to account for the inaccuracy.
From 2018, Voulgaris has been employed by the Dallas Mavericks as the director of quantitative
research and development.
9 - Phil Ivey Phil is easily one of the best poker players
ever, if not the greatest.
What hasn’t he done in his poker career at this point?
One of his career highlights is when he took down billionaire Andy Beal in a high-stakes
challenge that saw $16 million change ownership in three days.
Ivey started playing cards at an early age.
As a kid, he went up regularly with his grandfather.
He moved on later to the poker tables in Atlantic City, where he was known as “No Home Jerome”.
That’s because that was the name he had on the fake ID he used, and players would
see him around the clock at the poker tables!
Those first years weren’t great on the pockets for Ivey because he would routinely lose all
his money.
But it was those experiences that transformed him into the most feared poker player.
His first major victory was in 2000 when he won his first-ever World Series of Poker bracelet.
Two years later, he got another three all in the same year.
Ivey eventually accumulated 10 WSOP bracelets.
In his poker career, he’s accumulated over $26 million dollars strictly in tournament
winnings.
But Phil’s also played in some of the biggest cash games online and live.
He has legendary hands on the show High Stakes Poker, as well as huge wins online when Full
Tilt Poker was still around.
Many insiders speculate that his cash winnings in poker easily pushes his poker earnings
well over $100 million dollars!
8 - Billy Walters Now a businessman and philanthropist, Billy
remains one of the most notable legends in the gambling world.
He started gambling when he was just 9 years old.
This was only natural considering that his dad was a passionate poker player and his
uncle was a professional gambler.
He started his gambling career off with a big losing streak.
Reportedly, he had lost fifty grand by the time he was 22 and even lost his house at
one point.
Lucky for Billy though, the guy who he lost to, allowed him to settle the debt in 18 months
instead of actually taking his house.
With time, Billy got so good that he went on to amass millions of dollars in winnings
specifically betting on basketball and football.
And his winnings weren’t the rare one-off events.
Billy definitely knew what he was doing.
We’re talking about a 30-year winning streak which is enough to make anyone filthy rich.
On average, Billy pulled in $15 million dollars a year in profits.
Today, he’s reportedly worth $100 million – most of which is thanks to his incredibly
successful gambling career.
Throughout his life, he’s gotten in trouble with the law several times but never went
to prison.
But in 2017, he was found guilty for the first time for insider trading.
Billy was sentenced to 5 years in prison.
He served 2 years of the sentence before being pardoned by former President Donald Trump.
7 - Patrik Antonius This finnish poker pro wasn’t always destined
to be a legend in the poker world.
Career-wise, he had two other options, which were tennis and modeling.
From very early on, he dabbled in both of these spaces but tended to favor tennis and
he was once thought to be a rising tennis star in his home country.
But everything changed at 18 when he went with his friends to a casino.
His entire life changed as he went on to play poker for a living.
Antonius has had over 12 million dollars in tournament wins in poker.
In 2005, he had his first huge score when he came in second place in the Five Diamond
World Poker Classic tournament in Las Vegas.
That earned him a little over $1 million in the process.
His biggest cash in a tournament came in 2018, when he came in 2nd place in the Super High
Roller tournament in Macau for 3.1 million dollars.
His tournament poker isn’t what made him a legend.
It’s for his legendary pots playing cash games on the show High Stakes poker and playing
online on FullTilt poker!
To this day, Antonius still holds the record for the biggest online poker hand ever.
He won a little over $1.3 million dollars for his hand against Viktor Blom in 2009!
6 - Zeljko Ranogajec Australian-born Ranogajec is one of the biggest
gamblers ever.
His entry into gambling started back when he was in college, when he worked part-time
at a casino.
During his free time, he would try his hand at blackjack, in an effort to learn how to
make the perfect blackjack plays.
Ranogajec went on to quit his job to pursue his gambling career.
But with his consistent wins, Ranogajec was later banned from the Australian casinos.
So he switched his attention to Las Vegas, but the same thing happened.
He simply made too much money at the tables to avoid drawing attention.
Zeljko wasn’t interested in getting a real job, so he looked into other games to make
money.
He tried almost every table game and slot game available and he discovered his most
profitable game was Keno.
He once set the record for the world’s largest Keno Jackpot for roughly seven and a half
million dollars in 1994.
Later on, Zeljko began online gambling with horse racing.
At one time, supposedly a third of all the bets placed on Betfair were placed by Zeljko.
Around the same period, he supposedly also accounted for 6 to 8 percent of Australia’s
largest gambling company TabCorp’s annual $10 billion revenue.
Even though he’s been called the world’s biggest gambler and he’s speculated to have
roughly a 600 million australian dollar net worth, Ranogajec has denied both and said
that it’s all been a big exaggeration!
5 - Michael Jordan Michael Jordan is still the biggest name in
basketball.
And it’s well known that MJ had a thing gambling.
His first betting activity to leak to the public was back in 1991.
Jordan used a two-day break to allegedly go gamble at the tables.
That same year, a prolific and let’s just call him, unsavory character named James Bouler
was arrested and discovered to have a $57,000 dollar check from MJ.
While he tried to explain away the purpose of the funds, Jordan later owned up that the
check was indeed for his gambling losses to Bouler.
But more was to come.
In 1992, the police once again ran into several of Jordan’s big checks while investigating
the death of Eddie Dow, a bail bondsman.
These checks totaled $108,000 and according to Dow’s attorney, they were MJ’s settlement
of gambling debts.
More of MJ’s ways were exposed in 1993 when Richard Esquinas released his book titled,
“Michael and Me: Our Gambling Addiction…
My Cry for Help”.
In the book, Esquinas said Jordan had owed him a whopping $1.25 million from gambling
while playing golf.
But since he was having a hard time convincing the former champ to pay up, Esquinas had to
make do with the $300,000 dollars that MJ agreed to pay.
There are theories that MJ’s first retirement from basketball in 1994 really was a secret
2 year suspension by then NBA Commissioner David Stern for his gambling!
4 - Terrance Watanabe Terry was a business heir to the Oriental
Trading Company, which was launched by his dad Harry Watanabe in 1932.
Terry certainly did well to grow the family business!
He took over the company in 1977 and changed the focus of his family’s company to party
goods.
That was a wise business decision on his part.
Oriental Trading Company’s revenues ballooned to an annual average of $300 million dollars
after the switch.
That was a success by any measure, and you’d expect anyone who’s part of such a business
to stick around.
But, because his entire life had been growing the family business, Terry decided to retire
early.
In 2000, he sold his entire stake and resigned as CEO and president.
The details on the sale weren’t publicly available but how much Terry gambled away
offered at least some clue on how big the deal was.
With his new windfall, Terry headed to one of the largest gambling cities in the world
– Las Vegas – a not-so-good decision as he was to later find out.
Soon enough, he became revered in Las Vegas casinos as the biggest of the biggest high
rollers.
Because he gambled so big, he got special privileges no one else got.
At Caesars Palace, for instance, they created a special high roller tier for him called
“The Chairman''.
That tier ranked above the highest publicly known tier, called “Seven Stars”.
The Chairman tier gave Terry a monthly allowance of twelve and a half grand in airline tickets
and five hundred grand worth of credit in Caesar’s gift shops.
At one point, Terry gambled so much that he accounted for roughly 5.6% of all of Caesar’s
properties gambline revenues for 2007! Terry’s favorite casinos for blowing away his fortune
included Caesar’s Palace, The Rio, and Wynn Las Vegas.
After several years, he lost a jaw-dropping supposed amount of $204 million dollars!
Unfortunately, in 2017, Watanabe had to organize a GoFundMe fundraiser to pay for his medical
bills.
To find out more about Terry, click here!
3 - Guy Laliberte This Canadian is another billionaire on the
list who has plenty of money to burn!
He began his career as a street performer, and that’s around the time Laliberte co-founded
Cirque du Soleil, one of the biggest entertainment companies in the world.
Laiberte’s first big breakthrough came in 1984 when he was funded by the Canadian government
to perform on the 450th anniversary of the discovery of Canada.
And that’s basically how Cirque got started.
Cirque du Soleil was originally supposed to run for only a year, but the Canadian government
wanted an ongoing tour in other provinces.
When he’s not busy giving creative direction to Cirque, Laliberte is busy donating money
to high stakes professionals at the poker tables and also donating to charities.
Laliberte has famously played on High Stakes Poker where he’s involved in big pots.
But Guy’s mostly known for his massive online poker cash game losses.
His six online accounts have reportedly lost a total of $31 million dollars, making him
the biggest loser in online poker ever!
2 - Archie Karas This gambling story is that of rags to riches
then back to rags.
Archie’s famous for the largest and longest documented winning streak in casino gambling
history.
That streak is just known as “The Run”.
Archie drove to Las Vegas with just fifty bucks in his pocket back in December of 1992.
At that time, he was a well known poker pro in Los Angeles.
He’d routinely borrow money from different people and run his bankroll up to a couple
million dollars, but then lose it all.
This was what happened when he left for Vegas with 50 dollars.
Karas was known as one of the best Razz players in the world at that time, so he was easily
able to get a loan for ten grand when he got to Vegas.
And instead of running that money up to just a million or two, he turned that money into
more than $40 million dollars in a little over 2 years!
He quickly tripled ten grand into 30 grand in around 3 hours.
For six months, Archie got to $40 million dollars by playing poker, craps, and playing
pool.
According to Jack Binion, Archie was the biggest gambler he had ever seen.
For example, Karas would play pool for up to 40 grand a game!
Archie made the first million by playing pool with a big gambler.
He then switched to poker with the same gambler and won 3 more million in only a few days!
He decided to stick to poker.
For a period of 6 months, Archie won millions of dollars from the world’s best poker players
at the time, bringing his total bankroll to 17 million dollars.
He was able to beat legendary players such as Chip Reese and Stu Ungar for millions of
dollars.
Because his reputation and the stakes were too big for a lot of players, the action dried
up.
Archie then simply decided to leave his fate to chance and switched to craps and baccarat.
And that’s how he won the rest of the 23 million!
Karas was carrying around so much cash that he would have security guards escort him all
over the place.
But instead of leaving up huge, he decided to continue playing.
And the rest is just gambling history.
In roughly three weeks, Karas lost over $30 million dollars playing the same games, along
with a little bit of poker in between.
He decided to take a month-long break to try to change his luck.
But when he came back, the results didn’t change.
He ended up losing the rest of the money playing craps and baccarat!
1 - Jimmy Chagra He was a huge legendary figure during his
gambling life in Las Vegas.
While he didn’t have much luck at the tables, he was known to be a high stakes gambler and
a big tipper to anyone helping him out in Vegas.
There are stories of Chagra playing all six spots on a blackjack table, for $25,000 dollars
a hand.
Supposedly a pit boss once asked Jimmy if the casino could borrow $5 million dollars
from him.
The casino was short on cash because they had been hit hard by some high rollers, something
Jimmy said yes to.
He also supposedly paid off one cocktail waitress’s $50,000 mortgage when he heard she was raising
three kids by herself.
These are just a few of the legendary stories from Vegas surrounding Jimmy Chagra.
All that cash to gamble with came from his successful let’s call it, illegal substances
business.
In the 1970s, Chagra was a big time trafficker.
At the height of his business, he reportedly had as much as $100 million dollars in his
bank accounts, an equivalent of close to $500 million dollars in 2021.
Chagra’s glory as a high roller soon came to an end in August 1979 when he was finally
sentenced to 30 years on drug trafficking charges.
He was later released in 2003 amidst health concerns and succumbed to cancer in 2008.
Here’s what’s next!