Who says the house always wins? From crazy winning streaks to hitting the jackpot against all odds, some lucky players walk out of the casino with a big stack of cash. We got in touch with professional gamblers and experts across the gaming industry to hear their true tales of the biggest gambling wins.

biggest gambling wins

First, we spoke with Rebecca Liggero, an Industry Reporter, Interviewer, and Host for the well-known online gambling news site, Calvin Ayre, who also works as Global Brand Ambassador & Fact Checkerfor BodogBrand.com .

calvin ayre rebecca liggero

Rebecca Liggero, Reporter at Calvin Ayre

Rebecca was kind enough to let us in on the biggest gambling win she’s heard about in poker (and possibly in any type of gambling). In this case, we’re talking well over six figures.

“The most exciting gambling win I’ve ever come across during my 10 years in the industry is Antonio Esfandiari winning The Big One for ONE DROP poker tournament two years ago at the WSOP- the jackpot was $18,000,000!” - Becky Liggero from Calvin Ayre

In the famous tournament, Esfandiari went up against 48 professional poker players in the 2012 World Series of Poker. After the 3 day competition, he came out on top, winning $18,346,673!

Jim Makos, Pro Gambler

We also had the opportunity to catch up with Jim Makos, who’s a real Renaissance man at the casino. Jim not only makes his living as a professional gambler in blackjack, sports betting, and poker, but he also works as an investor and gambling writer.

Jim Makos pointed out that although the 2014 World Series of Poker winner didn’t beat Esfandiari’s $18 million from 2012, he still came pretty close.23 year old Daniel Colman, a pro online poker player from Holden, Massachusetts, won his first WSOP bracelet against some of the world’s best… taking home a cash prize of $15 million dollars.

Allen Kessler, Pro Poker Player

Allen Kessler, aka The Chainsaw, also makes big bucks as a pro poker player at events like World Poker Tour, World Series of Poker, and Heartland Poker Tour. What was his biggest win?

He told us his biggest win was, “$275,000 at the World Series of Poker in 2010”. He also mentioned taking home 10 grand playing a Stud 8 tournament. Not bad, Allen!

Winning that kind of money playing poker isn’t as easy as it seems. These tournaments can last for hours, and competitors go up against some of the best poker minds in the world.

kyle julius

Kyle Julius, Pro Poker Player

Even those that don’t win first place still take home a big check. Kyle Julius told us about his biggest win when he finished in second place at the 2012 Poker Stars Caribbean Adventure Main Event in 2012.

The first place winner, John Dibella took home a prize worth $1,750,000. So what’s the consolation prize for coming in second? $1.5 million! Nice Job Kyle.

What about professional poker player Todd Brunson who has made millions playing poker tournaments?

todd brunson

Todd Brunson, Pro Poker Player

Early in his career, Todd received the name Darkhorse for outlasting some of the best poker players in the industry. But for him, coming out on top at the poker tables runs in the family. 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 best win? It’s better to ask him how MANY big wins he’s had. Todd told us he’s won over “10 mil several times.” The man has made quite a name for himself after winning over $13.5 million in two days during a heads up, $50,000-$100,000 limit hold-em game.

Poker players aren’t the only ones who take home the biggest casino winnings. Gamblers can really come out on top making the right bets on sporting events.

Johnny Detroit, Pro Sports Handicapper

Johnny Detroit has worked as a professional sports handicapper and gambler for over 10 years. He got back to us with his biggest personal win in sports betting:

"We won over $100,000 when tying for 1st in Hilton Super Contest back in 2005 under Let It Ride Sports (maybe 2004?)"

What's the most you've won on a bet? Imagine winning $1.1 million on a single bet. That's what happened to boxing pro, Floyd Mayweather, in 2012 when he won $1.1 million betting on a college football game between Oregon and Arizona. Read more about Crazy Gambling Habits of Pro Athletes.

Meanwhile, Christopher Costigan, Founder and Publisher of the leading gambling news site, Gambling911.com told us:

Christopher Costigan, Founder of Gambling911

“One of the bigger wins Gambling911 has covered over the past decade is a $100,000 payout at Intertops.com on what was then the Florida Marlins to win the 2003 World Series.  The bet was placed shortly after the All Star Break when the Marlins did not appear to have a chance and still had very long odds.  Not exactly sure how much money was actually bet ($100 or $1000) but obviously the risk was way less than the eventual reward. “

“At the time there was some controversy as the odds actually would have paid out more than the $100,000 but Intertops claimed a policy of payouts being capped off at the $100,000.”

The biggest gambling prizes don’t always refer to the most money. Winning against the odds can prove just as exciting. Just ask a top sports broker at Trendbetting.com. Under the alias of JMH Sports 1, the pro sports handicapper told us his biggest win came when he “nailed a 12 team parlay”.


JMH Sports 1, Pro Sports Handicapper

So what does a 12 team parlay even mean? Well, parlay bets, or combos, refer to a single bet on two or more wagering outcomes in which the odds for the payout increase with the number of bets. The more teams you bet on, the higher the payout.

In the case of JMH Sports 1, wagering on the results for a 12 team parlay means significant payout. For example, someone placing a $10 12 team parlay could walk away with $21,000. After all, it’s pretty incredible to get it right 12 times.

Interested in getting involved in Sports Betting? Vegas Parlay represents an excellent resource for sports betting enthusiasts. Its editor, Tommy Lorenzo, has over 20 years experience in the industry.

Another sports betting expert from Trendbetting.com, Jeffrey Brandes, has especially good luck when it comes to horse racing. His most successful bet came in the Hollywood Gold Cup 2000.

jeffrey brandes

Jeffrey Brandes, Pro Sports Handicapper

That year racehorse, Early Pioneer, and jockey, Victor Espinoza, were the longest shot in the nine-horse field at 25-1, but placed 1st over favorite, General Challenge.

Brandes bet the race $90 across for himself and ended up winning $3,138 – That’s 34 times his bet! On the ride home, all Brandes could say was, “Come on Victor! Come on Victor!”

Want to learn more about horse racing? Head Off to the Races with American Horse Racing, an industry that generates over 26 billion dollars in the United States.

We also got a chance to speak with Larry Colcy, who told us some good tales of the biggest online casino winners. Known as the Gamblogger, Larry is an avid online casino player, especially slots, and writes all about the industry on his blog and YouTube channel.


Larry Colcy, Owner of Gamblogger

“I represent several casinos that have games with jackpots over a million… I can tell you about lots of big jackpot wins that I've written about over the last ten years!”

Our friend Larry told us a great story about a big win at High Noon Casino when a player took home half a million during free spins on the Triple Twister Slot. A player called “Mr. S” deposited $350 and claimed a 75% match bonus on March 28, 2014. He played for a while, winning here and there, before catching a big break with a $249,875 jackpot. No less than 3 days later, Mr. S took home another big win of $168,960 while playing the Triple Twister Slot.

For most of us, the idea of taking home millions in one sitting sounds absurd – But in the world of gambling, ordinary players turn into millionaires overnight. With such large prize pools and jackpots at stake, it’s no wonder why players get so excited over the mere prospect of a big gambling win.

With so much money to burn, celebrities attract a lot of attention with their ridiculous gambling wins. Read about stars that love to gamble like Ben Affleck, Matt Damon, and Ashton Kutcher who win thousands of dollars betting on their favorite card game or sporting event. Make sure to also get the inside look on the poker life in our interview with Sofia Lövgren.