10 Of The Best Gambling Winner Stories

To the victor the spoils!

It’s the one thing every gambler dreams about: the big win – that life-changing hand of cards, or spin of the wheel that whisks you away from your mundane life into the stratosphere of winners.

As a gambler, reading about other people who have won huge is like discovering heroes, except that they’re ordinary, everyday folk, from all walks of life… just like you and me. And that’s what’s so exciting: if they can win it, why can’t we?

So, for your titillation and fantasy fuel, here are some of the best gambling-winner stories we could find. Grab yourself a tasty beverage and soak up the triumph of these scores.

1 – Kerry Packer, Australia/Las Vegas

Not every wild gambling story features one person and their one or two wins; some legends deserve a little more explaining. Kerry Packer was an Australian entrepreneur, mogul and billionaire, who made his fortune through astute stock market investments. His love for gambling was absolutely legendary, particularly in his favourite stomping grounds, the Las Vegas Strip. He was known for being a wild and splashy player who tipped generously and often, and, most importantly, who knew how to quit while he was ahead. His massive, regular wins could strike fear into the hearts of casino operators, and spark joy in croupiers, servers and even emergency medical workers – legend has it that once, after they saved his life, Packer tipped the ambulance drivers and EMS workers $1m… each!

10 of the best gambling winner stories
10 of the best gambling winner stories

2 – Patricia Demauro, Borgata Hotel Casino and Spa, New Jersey

Craps is a game of odds – the more you roll, the more chances you have of hitting a 7 eventually, right? Well, Patricia Demauro proved that this gambler’s fallacy is, indeed, just that. During a single game of craps, she rolled the dice 154 times consecutively, and not once did she crap out. Not only did she beat a world record over the 4 hours 18 minutes she spent playing, but she also took home an undisclosed sum well into the hundreds of thousands of US dollars. Luck was certainly on her side, because the odds of a streak like that are about 1 in 1.56 trillion!

3 – Frederick Smith, Las Vegas, Nevada

What happens when the CEO of a startup gets desperate to keep his business afloat and takes a trip to Las Vegas? Well, if the person is Frederick Smith, founder of FedEx, apparently he gets what he needs. Back in 1973, FedEx was a small company, barely two years old and in deep financial trouble. Smith took the last $5000  – all they had for operating costs – to the Vegas blackjack tables. The $27,000 he returned with wasn’t enough to save the company, but it kept them going until they secured more funding to start growing into the giant they are today.

10 of the best gambling winner stories
10 of the best gambling winner stories

4 – Anonymous – Genting Highlands Casino, Malaysia

There are streaks, then there are STREAKS! As one player, who preferred to remain anonymous, at Malaysia’s Genting Highlands Casino discovered, it is possible to win an unimaginable 27 consecutive rounds of baccarat and walk off with a huge pile of cash. While the casino has maintained the player’s privacy and hasn’t confirmed the exact number, the player’s social media posts, which showed first his pile of chips, then his pile of cash, estimate the win at between RM5m and RM7m.

5 – Estelle Harrop, Sun International PE, South Africa

Progressive jackpot wins are the stuff dreams are made of, as Estelle Harrop of Port Elizabeth, South Africa discovered. Playing the SunStriker game, Estelle received a delightful R150,000 to take home. The SunStriker progressive jackpot slot is exclusive to Sun International’s brick-and-mortar casinos in South Africa, and carries a minimum jackpot of R750,000, making it well worth checking out if you visit the country.

10 of the best gambling winner stories

6 – Neil, Aberdeen, UK

The first time Neil decided to try his luck at online progressive slots, he became that rare unicorn, the person who strikes it lucky, and hard, right off the bat. In 2017, Neil had just started enjoying online slots, and was playing NetEnt’s Hall of Gods progressive jackpot slot, when he became an instant millionaire, bagging a staggering £6.3m.

7 – Elmer Sherwin, Mirage, Las Vegas

Elmer Sherwin is one of those insanely lucky cats who got lucky twice in the same place. The catch? Elmer’s wins came a full 16 years apart! On the same day that this casino opened on the infamous Las Vegas Strip, Sherwin walked in and won a staggering $4.6m. No small amount of money, even by today’s standards, it apparently wasn’t quite enough for Elmer, who returned 16 years later and walked off with over four times his original win: an ice-cold $21m.

10 of the best gambling winner stories
10 of the best gambling winner stories

8 – Beverly Whitten, Mountaineer Casino and Resort, New Cumberland

An avid slot player and retired teacher, Beverly Whitten was playing Golden Chambers at the Mountaineer Casino and Resort in West Virginia, USA, when she won big – almost $4m big! Beverly had been playing for just two hours when her winnings totaled a life-changing $3,718,311, which she chose to receive in monthly installments, rather than all at once.

9 – Jon Heywood, Cheshire, UK

It’s one thing to win a huge jackpot, but to then go ahead and hold the world record for the biggest online win for nearly a decade… well, that just feels like bragging! We joke, but Jon Heywood was the lucky winner of over £13m in 2015 – an amount that Guinness World Records have confirmed as the highest ever online casino win. Jon holds the record to this day; could you be the one to break it?

10 of the best gambling winner stories
10 of the best gambling winner stories

10 – ‘Young Engineer’, Excalibur, Las Vegas

Known only as the ‘Young Engineer’, this last entry on our list is most certainly not the least. This player, aged 25, one day walked up to a slot machine at the Las Vegas Excalibur hotel and casino. He placed $100 in coins into the machine, and was rewarded with an absolutely mind-blowing $39.7m. Like a true sensible engineer, he chose to receive his winnings in annual payments of a respectable $1.5m – certainly more than enough to live comfortably for the next 26 years or so until the payments ended.


Are you a winner?

All gamblers understand that the risk in chasing the big jackpots is real and that the winner’s circle is rarefied air. But that doesn’t mean you won’t be the next winner. The only way to win is to play – responsibly. If you are concerned about your playing and spending habits, read our articles on problem gambling and resources. And if you win, send us your story – it might end up right here on CasinoPlay.

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