The Nerd Side Of Life

What Are The Biggest Wins in Casino History?

We know that everyone loves to win money. Whether it be celebrities or just the average joe, we all love that feeling of beating the odds. We frequently hear about lottery winners and their spending habits. When an individual wins the lotto, they are picked up by the media immediately afterward, and then just a year or two later for an update on their lives. 

Many individuals are unaware that casino winners have won as much money as lotto winners on occasion. Playing slots and other games in casinos, both online and in-person, has resulted in gamblers winning millions of dollars. 

Here are just a few of the highest wins in both online and offline casino history. 

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Cynthia Jay Brennan 

Cynthia Jay Brennan, who was a cocktail server, became one of the world’s luckiest individuals when she won the greatest Megabucks prize in history in 2000. She was in Las Vegas playing Megabucks, a state-wide lotto jackpot slot machine when she won a total of $34,959,458.56. Within the following nine weeks, Brennan married her boyfriend, planned to travel the world with him, and overall celebrated her big win.  

Tragically, just nine weeks after Brennan scored her big win, she was in a horrible car crash. Cynthia was traveling in her beautiful new Camaro alongside her sister, Lela Jay when she was rear-ended at a red light by a drunk motorist with 16 prior offenses. Cynthia’s spine was shattered, and sadly, Lela died immediately. The motorist escaped with only a few scrapes. 

Today she is paralyzed from the waist down and is confined to a wheelchair. Her husband continues working and taking care of her. Cynthia claims she would return the $35 million if it meant that she was able to walk again and reunite with her beloved sister. 

Robert Keys (Online Winner) 

For Robert Keys, it all began when he decided to take advantage of the cashback bonus that the online Ozwin casino had to offer. Robert used his bonus entitlement as a VIP player to receive an $800 payback, which he then used to experiment with new games at the casino right away. 

After a few plays, Robert went back to his favorite RTG game, Diamond Fiesta, which has medium volatility. According to Robert, he intended to play only a few rounds and then he would call it a day.  


Robert noticed he was on a winning streak as soon as he began playing Diamond Fiesta. After receiving some fantastic bonuses from his first few spins, Robert expected his winning run to come to a stop sooner rather than later. However, that wasn’t the case and his wins continued to grow. The victories kept coming for the 40-year-old, allowing him to cash out a staggering $65,558.40. 

Robert said that he planned to buy a new car and treat some of his closest friends and family.  

Elmer Sherwin 

Elmer Sherwin was undoubtedly Las Vegas’ luckiest man. He became a Megabucks winner twice. He scored $4.6 million in 1989, just after the Mirage on the Las Vegas Strip opened. 

Elmer Sherwin, 92, a World War II veteran, took a seat at a Megabucks machine at the Cannery Casino & Hotel in Las Vegas on a Thursday afternoon in September 2005 because he said that he had a sense the machine was lucky. He guessed right, considering he won a prize of $21,147,947. 

Elmer decided to use the money to help his family, particularly his son and daughter-in-law, by donating a large sum to the Hurricane Katrina relief fund. 

Sadly, just two years later in 2007, Elmer Sherwin passed away.  

Jon Heywood (Online Winner) 

Jon Heywood, a 25-year-old British soldier who recently returned from a term of service in Afghanistan, was pursuing a minimum-wage job to make ends meet in October 2015. He was watching TV at home and thought it would be fun to try his luck at winning money, so he joined an online casino. 

Jon made a £30 deposit and started spinning, betting moderately and never exceeding £0.25 ($0.38) per spin. Jon’s technique was to bet on gambling machines with progressive jackpots, eventually landing on Mega Moolah, a game notorious for making millionaires. What is the explanation for this? It was chosen since it had the “biggest icon”! 

Jon began to whirl, his attention drawn primarily to a World War II tank film he was viewing. He discovered he had unlocked a bonus level after spinning for several moments and noticed “a big wheel rotating.” When it landed on the jackpot, Jon realized he’d won, thinking the sum was around £10,000 ($15,000). Nope, an incredible eight-digit number came up on the screen, indicating that Jon had just won $19 million from a single $0.38 spin. 

Despite the fact that he had just won a then-Guinness world record slot jackpot, he kept his head down and went about his business as usual, alerting only his supervisor awaiting confirmation from the casino before deciding what to do next. When he received confirmation, he began prioritizing his winnings, focusing on obtaining private healthcare for his gravely ill father.

Ending Thoughts 

Keep in mind the golden rule: the higher you climb, the harder you fall. Despite the fact that casinos will always have superiority, you should never stop dreaming big.

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