May 2022



Who says the casino always wins? Winning time after time or hitting a huge jackpot overnight, against all odds, some lucky players, walk out of the casino with pockets full of money. We reached out to professional players and gambling industry experts to hear their true stories of wins.

First, we talk to Rebecca Ligiero, a reporter, journalist and host of gambling news site Calvin Ayre, who also works as a global brand ambassador for Checkerfor BodogBrand.

Rebecca Liggero, Calvin Ayre reporter

Rebecca was kind enough to tell us about the biggest poker win (and probably gambling in general) she’s ever heard of. So, we’re talking six figures.

“The most amazing gambling win I’ve come across in my 10 years in the industry was Antonio Esfandiari winning “The Big One for ONE DROP” in the World Series of Poker (WSOP) poker tournament, the jackpot there was $18,000,000!” says Becky Ligiero of Calvin Ayre

In that famous tournament, Estafandiari played against 48 professional poker players, in the 2012 World Series of Poker. After 3 days of competition, he came out ahead, winning $18,346,673!

Jim Makos, Professional Player

We also had a chance to chat with Jim Makos, who is a true titan of the casino. Not only does Jim make his living playing professional blackjack, sports betting and poker, but he also works as an investor and gambling writer

Jim Makos also highlighted that while the World Series of Poker winner didn’t break Estafandriani’s $18 million record in 2012, he nevertheless came very close.Daniel Coleman, 23, a professional player from Holden, Massachusetts, won his first WSOP bracelet, playing against the strongest… and took home a prize of $15 million.

Allen Kessler, professional poker player

Allen Kessler, aka “Chainsaw,” has also made a lot of money as a professional poker player, playing at events like the World Series of Poker, the World Series of Poker and the Heartland Poker Tournament. Where was the biggest win?

He said his biggest win was $275,000 at the World Series of Poker in 2010. He also mentioned 10 wins in the Stud 8 tournament. Not bad, Allen!

Winning money this way is not as easy as it looks. These tournaments can last for hours with the best poker minds in the world as opponents.

Kyle Julius, Professional Poker Player

But even those who don’t come in first place take home decent sums. Kyle Julius told us about his biggest win when he placed second in the Poker Stars Caribbean Adventure Main Event in 2012.

John Dibella, who took first place, won a prize of $1,750,000. And what was the consolation prize for second place? $1.5 million! Nice work, Kyle.

What about professional gambler Todd Brunson, who made millions playing in poker tournaments?

Todd Brunson, professional poker player.

In the early days of his career, Todd was nicknamed “The Dark Horse” for outbidding the best in the poker industry. For him, however, being on the winner’s list was in the blood. His father, poker legend Doyle Brunson,

won the World Series of Poker twice and was inducted into the Poker Hall of Fame.

So what was Todd Brunson’s biggest win? Perhaps it’s better to ask him HOW many big wins did he have? Todd told us that he won over 10 million on multiple occasions. The man made a name for himself by winning $13.5 million in two days playing hold’em with

$50,000 to $100,000 limit.

However, poker players are not the only ones who can get big winnings at casinos. You can also make good money betting on sporting events.

Johnny Detroit, professional sports betting player

Johnny Detroit has worked as a professional gambler for 10 years. He tells us about his biggest win in sports betting:

“We won over $100,000 when we placed 1st in the Hilton Super Contest in 2005 (or maybe 2004?).”

What’s the largest amount you’ve ever won on a bet? And imagine what it would be like to win $1.1 million with just one bet! That was professional boxing, Floyd Mayweather, 2012, when he won $1.1 million by betting in a college soccer game between Oregon and Arizona. Learn more about the crazy gambling habits of professional athletes.

And here’s what Christopher Costigan, founder and publisher of one of the leading gaming sites,, tells us:

Christopher Costigan, founder of Gambling911

“One of the biggest wins that has been covered on Gambling911 in the last decade is the $100,000 payout at on a bet on whether the Florida Martins would win the 2003 World Series. The bet was made shortly after the break, when Martins’ situation was very unimportant and the odds of winning were very slim. I don’t know exactly how much money was bet ($100 or $1,000), but the chances of losing were much higher than winning the prize.”

“At the time there was still controversy about paying out much more than $100,000, but Intertops has a limit on the payout of winnings at the $100,000 bar.”

The biggest prizes in gambling are not always money. Winning a bet can sometimes be just as exciting. Let’s ask a sports broker from about that. A professional player nicknamed JMH Sports 1 told us that his best win was when he “won 12 team bets.”

JMH Sports 1,a professional sports betting player

So, what is a team betting? Well, when you make a wager or bet, it is a single or double or more, and your winnings increase in proportion to how many bets were made. The more teams you beat, the higher your prize.

Thus, the fact that JMH Sports 1 won 12 team bets means he got a decent amount. For example, someone who bets $10 in 12 team bets will get $21,000. Besides, it’s amazingly satisfying to be right 12 times in a row.

Want to get involved in sports betting? Vegas Parlay presents a great resource for sports enthusiasts. Its author, Tommy Lorenzo, has been in the field for over 20 years. Another sports betting expert with is Jeffrey Brandes, he is especially good when it comes to horse racing. His most successful game was the 2000 Hollywood Gold Cup.

Jeffrey Brandes, professional sports betting gambler

That year, horse Ely Pioneer and jockey Victor Espinoza, posted the most time in the field for 9 horses at 25-1, but came before the favorite, General Challenge.

Brandes bet $90 and won $3,138 – 34 times his bet! On the way home, all Brandes could say was, “Come on, Victor! Come on, Victor!”

We also had a chance to talk to Larry Colsey, who told us a couple of tales about the biggest casino winners.

Larry, also known as Gamblogger, is an avid casino player, especially slot machines and he writes about everything related to the industry on his blog and YouTube channel.

Larry Colcy, Owner of Gamblogger

“I represent several casinos that have had jackpot games over a million… I can tell you about the many jackpot wins I’ve written about in the last ten years!”

Our friend Larry told us an amazing story about a big win at High Noon Casino when a player took home half a million by doing a couple of free spins on the Triple Twister Slot machine. A player named “Mr. S” deposited $350 and bet a 75% bonus in March 2014. He played a little here and there and then snapped up the $249,875 jackpot. As recently as three days later, Mr. C hit the jackpot again, a jackpot of $168,960, when he played Triple Twister Slot.

To most of us, the thought of taking home millions in one go sounds absurd, but in the world of gambling, ordinary players become millionaires overnight. With such large prizes and jackpots, it’s no wonder they’re so obsessed with taking home a grand victory.

Celebrities who are loaded with money are also getting a lot of attention for their amazing gambling victories. Read about celebrities who love to gamble, like Ben Affleck, Mat Damon and Ashton Kutcher, who have won thousands of dollars at their favorite card games or sports competitions.


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