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Famous Big Winners

The ultimate dream for most gamblers is to one day land a big win that will change their lives forever. That’s often the main reason they gamble. It never happens for most gamblers of course, as life-changing wins are not particularly common. Even just the slight possibility of becoming rich is enough for many to keep betting or playing though.

This is fair enough, as a big win can happen to anyone. It’s not always the most knowledgeable or skilled gamblers who win big, as winning a slot machine jackpot or a lottery jackpot is down to simple good fortune. Skill and knowledge can play a part in some forms of gambling of course, and especially in poker and sports betting, but there are plenty of ways to win when all that’s required is a large slice of luck.

History is full of gamblers that were either lucky enough, or clever enough, to win huge amounts of money. On this page we look at a few of the biggest and most famous winners ever, in no particular order. If you ever feel like the big win will never happen for you, remember that most people on this page probably felt the same once.

List of Winners

Gloria McKenzie

Gloria McKenzie became the largest single winner of the Powerball lottery in the United States when she scooped $590 million in May 2013. The Florida grandmother, 84, beat odds of 1 in 175 million to win the jackpot. She won the massive prize after buying her ticket in a local supermarket when the person in front of her in the queue had let her go first. That act of kindness cost someone a lot of money, but it’s unlikely that Gloria is complaining.

Cynthia Jay-Brennan

Cynthia Jay-Brennan has experienced good and bad fortune in extremes, both in 2001. First, the cocktail waitress won a huge jackpot when playing slots. At $35 million it was the largest ever slot jackpot at the time. She got married to her boyfriend and started making plans to travel the world, no doubt thinking she just how lucky she was.

In a horrible twist of fate, just a few weeks later she was involved in car accident when a drunken driver slammed into her car. Her sister, Lela, was killed and Cynthia was paralyzed from her chest down.

Gonazol Garcia-Pelayo

Spaniard Gonazol Garcia-Pelayo was a record producer but his real passions were mathematics and roulette. During the 1990s he determined that not all casino roulette wheels were entirely random, and that some favored certain numbers more than others. The idea of biased wheels was not a completely new concept and others had made money from such wheels before, but Garcia-Pelayo took things to another level.

Starting with Spanish casinos, he watched roulette wheels for hours and recorded the results of thousands of spins. He even enlisted the help of his children. He then analyzed the results to see which wheels had a bias. When the time was right, he bet according to the bias and turned the house edge around. After winning a certain amount in one casino he would then move on to another.

The Spanish casinos caught on to him after a while, so he took his system to Las Vegas and continued to profit. Eventually he became too well-known and had to stop, but not before he had made a small fortune. He was sued by one Spanish casino, but the court ruled in his favor saying he had not acted illegally. Casinos now have processes in place to avoid biased wheels.

Elmer Sherwin

Elmer Sherwin will surely go down in history as the luckiest slots player of all time. The Megabucks progressive jackpot is one of the biggest slot jackpots around, and Sherwin has unbelievably won it twice. He first won $4.6 million at the Mirage casino in Las Vegas, in 1989. Some 16 years later he won it again. This time he was playing at the Cannery, and won the massive amount of $21 million.

Conor Murphy

The Cheltenham Festival is a major horse racing meeting in the UK, and attracts a lot of betting interest. At the 2012 festival, a young man became the envy of many horse racing bettors when he won an incredible wager that had been placed the previous year.

Conor Murphy won £1 million on a five horse accumulator that he had placed around Christmas time in 2011. Horse racing accumulators, which involve picking the winners of multiple races, are notoriously difficult to win. To win one that was placed nearly three months before the races were due to be run is an impressive feat to say the least.

Ashley Revell

In 2004, Brit Ashley Revell quite literally gambled everything he had. He sold everything he owned, cashed in his savings, and took the whole lot to a Las Vegas casino. Revell placed every penny on a single bet. His bankroll came to around $135,000, and he risked it all on spin of the roulette wheel. He bet on red and, surrounded by an audience, he watched as the wheel spun and the ball settled in red 7.

Although the sums involved are not as high as some of the other winners here, Revell definitely deserves a mention. Clearly not a good advert for sensible bankroll management, he nonetheless had the courage to put everything on the line in a game of pure chance. After giving the croupier a substantial tip, Revell used his winnings to set up an online poker room.

Charlie Wells

Charlie Wells was something of a celebrity gambler in his time. He was also a confidence trickster who spent time in prison. In 1891 he visited Monte Carlo with the proceeds of one of his cons. Starting with around £4,000, he played roulette for 11 straight hours and managed to win over one million francs. That was a simply astonishing amount of money back then. Wells broke the bank several times during his session, meaning that he won all the chips at the table and the casino had to send for more.

He returned later the same year and, over three days, won another million francs. Legend has it he placed successful bets on the number five for five consecutive spins. It’s widely believed that Wells was not cheating, but rather that he went on an incredibly lucky streak using the high-risk Martingale system of doubling his stakes whenever he lost a bet. It turned out for well for him, but the story could easily have been very different. The Martingale system has ruined far more gamblers than it has helped.

Don Johnson

Don Johnson (not the actor) went on an incredible winning streak in Atlantic City casinos in 2011. He played only blackjack, and managed to win an amazing $15 Million. During his streak he played at three different casinos. The Borgota Hotel, the Tropicana, and the Casino & Spa were all taken for some serious money. Unbelievably, Johnson is not known to be a professional gambler or card counter. It’s believed he simply played well and got incredibly lucky.

Norwegian Peter

An online casino player in Norway, known only as Peter, won nearly €5 million in 2010. He was playing a slot machine and won the progressive jackpot, much to his disbelief. This is one of the biggest slot machine jackpots ever won online, and was just below the largest of the time of over €6 million. In the years that followed there have been a few even larger jackpots won, but it’s fair to say that Peter would have been happy with his win.

Colin and Chris Weir

Colin and Chris Weir won the biggest ever Euromillions lottery jackpot in July 2011. The Scottish couple, who have been married for over 30 years, won a staggering £161 million. As you would expect from any lottery winner, they have splashed out since. They haven’t spent it all on themselves though, and have bought expensive gifts (including luxury cars) for friends and family.

They have been very generous in their charitable donations too. In 2015 they launched The Weir Foundation, with a £5m endowments, and they’ve given hundreds of thousands of points to the soccer club they support (Partick Thistle).

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