The Biggest Casino Wins of all Times

What are the biggest casino wins of all times, and did they make the winners happy?

Anyone with the slightest interest in betting would have, at some point, been attracted by the possibility of becoming rich in an instant. It is a common belief that anyone who plays casino games is bound to lose, but would they be as popular as they are if that were the case? Soome people win so much money in a casino, it transformed their lives in seconds.

That said, it is worth noting that while these individuals were fortunate, not everybody can have their lucky day (the last entry can be considered living proof of that). Gambling always involves a certain level of risk and must always be approached with caution. The stories we feature on this list are the exemption, not the rule.

Below, we have compiled a list of some of the biggest casino winners and their staggering winnings.

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John Tippin: $11.9 Million

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John Tippin.

Mr John Tippin couldn’t have imagined that his $9 would turn into millions, but that is precisely what happened to him. He was a Postal Service employee from Honolulu, Hawaii. HE must have experienced a surreal moment when he hit the Megabucks jackpot at the Las Vegas Hilton during his vacation in 1996. Winning an astonishing $11.9 million, an amount that changed his life forever.

Tippin’s jackpot win also broke the previous world record of $10.9 million, which was also won on a Las Vegas Megabucks progressive slot machine

Later, in 2001, Tippin published a book titled “I Did It: My Life After Megabucks” to share his experience of becoming an instant millionaire, which also involved him sadly turning to alcohol.

His book, which also landed on Amazon’s bestseller list, described his life after five years of winning the “Big One.”

Elmer Sherwin: $4.65 Million and $21.14 Million

Some individuals appear to be born with the lucky gene. World War II veteran Elmer Sherwin might consider himself one of those people when he landed the biggest jackpot on a slot machine, not once but twice during his life.

His winnings totaling around a whopping $26 million! In 1989, Sherwin visited the Mirage on the Las Vegas Strip, which had only opened ten hours earlier.

Moreover, the Megabucks slot machine had also just been introduced at the newly-opened casino establishment. The casino paid out $4.65 million to the then 76-year-old for a mere $3 stake.

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Elmer Sherwin.

According to a spokesperson for the Mirage, Sherwin played for over an hour. He invested nearly $100 before finally winning what was then claimed to be the biggest jackpot ever won on a slot game in Las Vegas.

Sixteen years later, in September 2005, at 91, Sherwin revisited Vegas and won another Megabucks jackpot of $21.14 million at the Cannery Casino & Hotel. It is also worth mentioning that Sherwin was charitable with his winnings, notably donating a large portion of the money he won to those affected by Hurricane Katrina.

Jon Heywood: €17.9 Million

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John Heywood. Image: PA.

In 2015, 26-year-old soldier Jon Heywood became rich playing the Mega Moolah slot from his home in Cheshire, United Kingdom.

As it turned out, Heywood won a gobsmacking £13,209,300 for just 25p per spin. This happened just after he signed up with the online casino Betway.

Initially awarded to the Brit in Pound Sterling, the amount converted to €17,879,645. Heywood’s winning story earned him a Guinness World Record for the largest jackpot payout in an online slot game.

After receiving his winnings, Heywood revealed that he would spend them on the best possible treatment for his father, who had been waiting for a lung and heart transplant. The substantial win also allowed the young soldier to pay for a Mediterranean cruise for his family.

Cynthia Jay-Brennan: $34.95 Million

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Cynthia Jay.

Cocktail waitress Cynthia Jay Brennan became a prime example of the phrase “rags to riches” when she hit a staggering jackpot In 2000, Jay-Brennan hit the biggest jackpot on the Megabucks slot machine, resulting in a substantial win of $34,959,458.56.

It was at her then-boyfriend’s mother’s birthday party in Las Vegas that Jay-Brennan decided to try her luck, and after nine rounds of the game, she emerged as an instant millionaire. Her win allowed her to quit her job, marry her boyfriend, and ultimately enjoy her newfound wealth.

Shortly after her honeymoon, she established a will and set up trust funds for her family members. Moreover, she also paid off any of her family members’ debts.

Tragically, weeks after her win, during a family visit to Las Vegas, Jay-Brennan had a life-altering car crash along with her elder sister, Lela. She lost her sister and was left paralyzed from the waist down. Cynthia looks for ways to give back to others who have faced similar fates by donating significant amounts of money to charitable causes.

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Anonymous: $39.7 Million

Even though some of the biggest jackpot winners become famous. In 2003, one lucky individual from Los Angeles chose anonymity when he landed a substantial win of $39.7 million. He went to Excalibur Casino to kill time while waiting for a basketball game. A little later, he made history by winning the biggest jackpot on a slot machine.

With a deposit of just $100, the individual, revealed to be 25 years old, defied the odds and walked away with an enormous sum of money. While there are no further details regarding the winner, Excalibur Casino revealed that he opted to receive his winnings in yearly installments of $1.5 million over the next 25 years.

Katrina Bookman: $43 Million

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Katarina Bookman Selfie.

This entry may be the oddest and, indeed, the most frustrating. In 2016, Katrina Bookman won a staggering $43 million jackpot on the Sphinx Wild slot machine at a New York-based casino. However, her joy didn’t last very long as the casino annulled her winnings, citing “technical issues”.

Bookman hired a lawyer to sue the casino. When the attorney requested additional information, the casino refused to comment further.

Ultimately, Bookman and her legal representatives contended that at least $6500, the maximum payout on the slot. It would be paid out due to malfunction, they commented.

It must be heartbreaking to think you might have won $43 million only for it to be taken away from you.

Even the biggest casino wins of all times don’t guarantee happiness. However, we’d be willing to give them a try.