Biggest Casino Wins in History: Stories That Inspire

Every gambler dreams of winning big at some point, but do these fantasies ever come true? Yes, some players do win life-changing fortunes in the casino, and they can inspire other gamblers in the process. That said, we're going to discuss the biggest casino wins in history with an emphasis on the positive (maybe minus the first story). In other words, we won't be covering Megabucks Curse winners and their ensuing tragedies.

1. Archie Karas - The $40 Million Run

Greek-born gambler Archie Karas is famous for the greatest gambling run in history-simply known as "The Run." In 1992, Karas found himself in LA broke and down to $50 after losing his bankroll to poker legends Doyle Brunson and Chip Reese. Rather than take a breather, he traveled to Las Vegas and convinced a poker friend to loan him $10,000. Karas proceeded to run his bankroll up to $7 million through a combination of high-stakes pool games and poker. By this point, his reputation proceeded him and made pool games impossible to find. Poker was also a tough sell, so he could only play elite pros like Chip Reese, Johnny Moss, Puggy Pearson, and Reese. His amazing run continued as he more than doubled his bankroll to $17 million against these top pros. Karas would eventually play craps and run his bankroll up to $40 million, completing a journey from $50 to $40,000,000 in three years (1992-95). Unfortunately, he would lose all the money within months through a combination of craps, poker, and baccarat. But Karas has since went on multiple 7-figure runs since then.

2. Kerry Packer - Billionaire Gets $40 Million Richer

Late Australian billionaire Kerry Packer could be interchangeable with Karas since he also won $40 million. We put him at number two, though, because his win isn't as dramatic as starting with $50. In fact, Packer never had to worry about his bankroll since he was Australia's richest man at one point with over a A$7 billion net worth. Nevertheless, his story is still highly interesting due to the sheer stakes he was playing. Packer went on a Las Vegas vacation and began playing high stakes at the MGM Grand. The Aussie media mogul was doing so well that he eventually started betting $200,000 per hand on six private blackjack tables. The end result was a $40m win, matching Karas for the biggest known gambling success story.

3. Unknown Software Engineer - $39.7 Million Slots Jackpot

You don't have to draw out a $40 million win over three years like Karas did, or even a lengthy hotel stay like Packer. Case in point, a software engineer from LA hit the biggest slots jackpot ever at Excalibur Casino in mere hours. The 25-year-old was in town on business when he began playing Megabucks at the Excalibur. As alluded to before, Megabucks is the subject of many cursed winners, but not this time. The engineer hit a record-breaking $39.7 million jackpot in 2003 and remained anonymous. He took annuity payments, giving him $1.5 million over 26 years, meaning he's still receiving these massive annual payments even today.

4. 23 Years of Dedication Turns into $27.6 Million

Perseverance doesn't always pay off with regard to gambling because you're facing a house edge. However, one woman saw her dedication pay off in the form of a $27.6 million jackpot. The unidentified gambler had been playing slot machines for 23 years when she sat down for a short session at Palace Station Hotel & Casino in Las Vegas. The woman spent $300 winning the $27.6m prize on Megabucks, thus leading to the big payoff after over two decades of gambling. Speaking to reporters following her 1998 windfall, the anonymous player said that she was going to share the winnings with her three children and grandchild.

5. Elmer Sherwin Wins a Collective $25.6 Million in Slots Jackpots

Most people never hit a multimillion-dollar jackpot in their lifetime. Assuming they do, it can take decades like in the story above. But Elmer Sherwin not only won big once, but twice within the span of 16 years. His first big win came when he and his wife visited family in the Vegas area in 1989. Sherwin normally only gambled $100 at a time, which he ran through at the Mirage Hotel & Casino on a seemingly regular slots session. However, the 76-year-old retiree asked his wife for another $20, which he used to win a $4.65 million jackpot on Megabucks. Sherwin then set a goal of becoming the first person to win a huge slots jackpot twice in a lifetime. He realized this goal in 2005 after hitting a $21.1 million prize at Vegas' Cannery Casino. The 92-year-old gave most of his money to charities and victims of Hurricane Katrina afterward, before passing away two years later in 2007.

6. Belgian Player Wins the Biggest Online Slots Jackpot at $23.6 Million

All the wins covered so far have occurred in land-based casinos, but the biggest casino wins can also happen at gaming sites. Case in point, a Belgian player won €19.4 million ($23.6m) while playing online slots in 2021. The player deposited just €15 and began playing Microgaming's Absolutely Mad Mega Moolah. His small bankroll turned into the biggest online slots jackpot in history. While the Belgian gambler wished to remain anonymous, he did speak to the press afterward. "The feeling at that moment is just indescribable," he said. "At first you can hardly believe it, and I think it will take a long time to sink in completely. It was on my last spin that it happened."

7. British Soldier Wins $19.9 Million - Helps Ill Father with Winnings

Several bigger online slots jackpots have eclipsed the $19.9 million that Jonathan Heywood won in 2015. But this list is as much about inspirational wins as it is the the largest casino payouts. Therefore, Heywood qualifies based on his story and huge online slots prize. The British soldier, who toured in Afghanistan, was betting 25p per spin during an online gambling session in 2015. Normally such small spins don't amount to life-changing fortunes, but they did in this case when Heywood won £13.2 ($19.9m) through Mega Moolah. He became an overnight celebrity in the UK and earned more than enough money to get his ailing father heart and lung transplants. "[The win is] amazing. The first thing I will spend it on is the best possible medical treatment for my dad." Heywood added that he planned to be conservative with the rest of the winnings, possibly only splurging on a Bentley Continental GT for the time being.