Top 10 Inspirational Gambling Success Stories

We’ve all heard of stories where a person has lost everything to the point of no return. However, few have dared to keep going and even won incredible amounts of money for the risk they took. Stories like that have often been relegated to fantasy and myths due to their odds but they do happen. 

Be it a desperate mind that comes up with unique strategies or just plain luck, there are many success stories that will leave you speechless in the gambling community. Let’s take a look at 10 such examples of people with inspirational and motivating stories behind their gambling careers where they achieved immense success. 

10. Teacher Spends 14 Cents and Wins $1,300

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Kevin Maselli is a teacher from New Jersey who liked to bet small amounts on football matches. When he appeared on ESPN, he acknowledged he and his girlfriend had never won much but liked to try.

One day Kevin put all he had in his DraftKings account up on the line to win at the NCAA tournament game. That might sound impressive but all he had was $0.14 in his bankroll.

After discussing his ideas with his girlfriend on the round-of-32 games, he placed a few penny parlays strategically. Maselli went to sleep only to wake the next day to an email from DraftKings congratulating him on his $1,345.78 win! 

The story had a romantic end as well, Maselli planned on putting the money into a ring fund which would come in handy when he would propose to his girlfriend. 

9. From Prohibition to a Casino Chain

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Benny Binion’s story is rife with crime and disregard for the law. He started off smuggling alcohol during the prohibition era. However, his early years as a small-time crook and rum runner would soon be over when he moved from El Paso, Texas to Las Vegas. 

Soon he would purchase the Eldorado Club and the Apache Hotel after many failed investments and open them under the name Binion's Horseshoe. The Horseshoe casino would dominate Vegas as it let players gamble with high stakes which helped it earn favor with high rollers.

Although Binion himself wasn’t a good player, he organized many spectacular matches that captivated the public with stakes as high as they can be. 

He was inducted into the Poker Hall of Fame for his contributions to the sport in 1990 after his death. 

8. Grandma Wins $100,000

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Most of you may not have even heard of Patricia Demauro, many still probably don’t remember her. An unassuming sweet grandma she may be, but she also holds the title of the longest-ever winning streak in craps. 

In May of 2009, Demauro was at the Borgata Casino in Atlantic City enjoying herself. With just $100 to her name, few could have thought she was going to be a famous celebrity with her actions. She proceeded to play Craps for 4 hours and 18 minutes straight and won 154 consecutive rolls. That’s not a one in a billion chance, that's a one in 1.56 trillion chance! 

She won more than $100,000 for her troubles and she remained very humble throughout all of it. In fact, she didn’t even know how rare her winning streak was as she was too busy having fun. 

7. From the Pitch to the Ring and Then to Betting

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Curtis Woodhouse had a knack to prove his critics wrong. Born on February 26, 1980, Woodhouse started off his career as a youth player for a football club named Sheffield United. However, within just several years he switched to Boxing without any experience and dominated his opponents there. 

No doubt then that he brought the same ferocity when it came to his gambling career. At one point, Woodhouse was spending over $500 a day gambling, focussing on sports betting.

With controversy always following him, he had to prove his doubters wrong and he did when he won $62,000 on a bet. He would go on to win a bet on the premier league match which won him a further $1.2 million. 

Woodhouse has had an interesting career, to say the least, and his wins be it in football, boxing, or betting are an inspiration to everybody

6. The Secretive Sports Better

Billy Mitchell has been a sport better for over 30 years now but most people hardly know about him. Born in 1960 in Las Vegas, Mitchell was exposed to gambling from a young age. He started young as well, by the time the 80s rolled around he decided to learn how to analyze teams and predict their performance. 

Although he came from humble beginnings, Billy has garnered a small yet loyal fan following due to his accuracy and research expertise. He also likes to bet big amounts as he bet $170,000 on the Green Bay Packers in Super Bowl XXXI and his 2012 Super Bowl bet was on the New York Giants where he won more than $1 million through a single bet. 

Mitchell has always kept a low profile and kept himself grounded in his humble roots despite being a millionaire.

5. Keeping the Moneymaker Tradition Alive

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Chris Moneymaker was just an average guy with an accounting job in the early 2000s. He did like to play online poker tournaments and enrolled in an $86 poker tournament in PokerStars. This would get him qualified for the 2003 WSOP Main Event and the rest is history. 

With a full hand against Sam Fahra’s two pairs, Chris won the first prize of $2.5 million. This would send shockwaves throughout the gambling community and give Moneymaker a bigger platform and stardom.

After that, he would continue to win smaller tournaments and amass $4 million through poker, and in 2019, he was inducted into the Poker Hall of Fame.

Keeping to his last name, he had already quit his job to pursue his own company and even wrote an autobiography!

4. $5 Makes a Millionaire

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An elderly couple enjoying their visit to the Borgata Hotel Casino in Atlantic City was shocked in the best way possible. 85-year-old Harold McDowell and his wife were playing three-card poker but had their backs turned to each other.

Surprisingly, her husband would get a royal straight flush of diamonds, which has odds of 1 in 20 million. McDowell’s $5 on the 6-Card Bonus was now a $1,000,000 win.

The win couldn’t have come sooner, as his wife became cancer-free just a day ago after several surgeries. At first, she didn’t even believe the poor guy, but they would later go on to say "It must be the luck of the Irish". 

The Borgata Casino would congratulate them on their Facebook page, and people who followed the page went above and beyond to congratulate the couple.

3. The Most Successful Female Poker Player

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Vanessa Selbst is a name that has become ubiquitous in poker over the years. However, her rise wasn’t an easy one, and that’s what makes it all the more inspirational. Selbst started playing poker while attending university and soon realized she had the talent and willingness to make a name for herself.

Her initial investment of $50 turned into $100,000 in just two years, and she had made quite a name for herself.

After that, she started competing and won three WSOP bracelets and two North American Poker Tour titles. Her fortitude and mastery of the game have also helped her earn $11 million in live tournaments and have ranked her as the best female poker player many times.

Selbst’s journey in a male-dominated sphere like gambling and earning fame and fortune is incredibly inspirational, especially for younger women who would also like to participate in the sport.

2. A Small Businessman Wins a Fortune

The story of Don Johnson starts off with him being an ordinary small businessman. The 2010s were turbulent times for Atlantic City casinos, as the effects of the 2008 financial crisis left them searching desperately for people who would want to gamble big amounts. In 2010, Johnson was offered to play at the Tropicana, and he would do it by his rules.

He proposed changes like the dealer having to stay at soft 17, six decks, re-splitting aces, a 20% refund if he lost more than 500,000, and much more. Thus started his unlikely gambling career, where in just 12 hours he won $1.2 million. That was just the beginning, though, as throughout a 6-month period he won $6 million from Tropicana, $4 million from Caesar’s Atlantic City, and $5 million from the Borgata Hotel Casino.

His total winnings were calculated to be a staggering $15 million, and he got banned from two of the casinos.

1. From $50 to $40 Million

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The story of Archie Karas is filled with hardships and rough edges. However, his success was a statement to some and an inspirational success story to others. Born in Greece in 1950, Karas moved to the US in 1966 with just $50 to his name. Karas, sold on the American dream, started off working as a waiter and dishwasher but soon saw the potential casino games had.

He would start playing high-stakes poker and pool soon, and his talent was hard to miss. Many of you might remember his incredible winning streak in the 1990s, when he turned $50 into more than $40 million. In 1992, he won $1 million against Johnny Chan, who was an undefeated two-time WSOP champion.

Back in 1995, he also won $17 million against the legendary Doyle Brunson, which helped create his legacy as one of the best in the game.

Sometimes a small losing streak can really take out all the fun and motivation to play games. We hope these 10 people helped inspire you to keep striving for that big win. If there was one thing in common between all of these people, it was their resilience and tendency to try their luck.

The people mentioned on this list are just a few of the people who have incredibly inspirational stories behind their gambling careers. So what are you waiting for? Get back to playing and win it big! We hope we get to showcase your story to the world too!