Regular casino players know that there’s a big difference between winning and winning big. Walking away with more cash than you came with is always cause for celebration, but some visits to the casino offer a whole lot more. Everyone who has ever taken a seat at a table game or pulled the arm of a slot machine has dreamed of making it on this list, but only a few can claim the title of biggest casino winners in modern history. Whether you’re looking for inspiration ahead of your next gaming trip or you’re just in the mood to see the type of win you could land if Lady Luck gives you a smile, there are plenty of reasons to enjoy this comprehensive list of the biggest casino wins in modern history. Enough chit chat, let’s get started!

The Suitcase Man

Separating the facts from the myths and urban legends is sometimes tough when it comes to casino history. After all, records of big time wins aren’t exactly available for research. Luckily, the story of the Suitcase Man has been confirmed by a number of witnesses. On September 24, 1980, William Lee Bergstrom decided to pay Binion’s Horseshoe Casino in Las Vegas a visit, but he didn’t come empty handed. Bergstrom brought two suitcases with him, one filled with cash and one empty. All told, the suitcase contained an impressive sum of $777,000. We’re guessing Bergstrom had somewhere else to be on that fateful day, because he wasted no time in getting to the action.

Bergstrom promptly made his way to a craps table at the Horseshoe and put the entire suitcase worth of cash on the Don’t Pass line. The dice were thrown and either a two or three was the result, because in a single roll the Suitcase Man doubled his cash. With his winnings in the formerly empty suitcase, Bergstrom proceeded to leave the casino, finishing up an extremely profitable 10 minute visit.

Single Spin Success

Believers of hot and cold streaks at slot machines will insist that finding a warm machine is key to bringing home some extra cash. While the facts behind this hypothesis suggest otherwise, there’s no doubt that some machines seem to go on winning streaks from time to time. On June 1, 1999, a Megabucks slot machine at Caesars Palace got hot at the perfect time for an anonymous, 49-year-old Illinois business consultant. The man took a seat, placed $10 into the machine, and hit the progressive jackpot on his very first spin. In the blink of an eye, his $10 wager was transformed into a payday in excess of $21.3 million. There’s no word on whether or not he went back to his business consulting job, but we wouldn’t be surprised if playing Megabucks became one of his key recommendations.

The Cursed Jackpot

Hitting the jackpot is typically a turning point in people’s lives, introducing them to the benefits of being extremely wealthy. For Las Vegas cocktail waitress Cynthia Jay-Brennan, however, winning a then-record Megabucks jackpot of $34.9 million at the former Desert Inn hotel-casino marked the start of a terrible chain of events. Just six weeks after her big win, Jay-Brennen’s car was hit by a drunk driver and her sister was killed on the spot. Jay-Brennen was paralyzed from the neck down as a result of the wreck. In an interview following the tragic event, Jay-Brennen claimed that she’d gladly return the prize money for a chance to go back in time and avoid the auto accident.

Blackjack in Atlantic City

In early 2011, the casino industry was struggling, as the recession kept people out of casinos for years at a time. In order to entice players to visit, casinos were forced to offer heightened discounts and incentives on a variety of games. Don Johnson, a corporate executive from Pennsylvania, was just one of many players who visited Atlantic City to take advantage of these offers. Over the course of a few months, Johnson successfully leveraged improved incentives and basic strategy to win an estimated $15 million at the blackjack tables. The three Atlantic City casinos he visited, including Caesars, confirmed that he didn’t use any tricks or card counting techniques. Instead, he just took advantage of the offers that were on the table. For Johnson, the recession came to an abrupt and fortunate end after this hot streak.

Pennies Make Pounds

Penny slots catch a lot of flak for their high house advantages and small payouts, but that doesn’t mean winning at these machines is impossible. In January 2014, one lucky penny-dropper hit the big time at a Wheel of Fortune progressive slot machine at Caesars Palace. All told, the player won more than $4.5 million on the spin, marking an astronomical return from a one cent bet. As it turns out, playing penny slots isn’t just a strategy to get free drinks. Find a progressive with a high jackpot, and you could be the next player to turn a penny into a fortune in the blink of an eye.

These examples are some of the most exciting, high profile wins in the modern history of the casino industry, but they are just the tip of the iceberg when it comes to huge wins. Whether players prefer to maintain a bit of privacy or they win when no one is watching, nailing down a definitive list of jackpot kings and queens is all but impossible. Still, these cases highlight the fact that life-changing wins are achieved all the time in casinos around the world, and that’s a great excuse for you to put your luck to the test right about now. Luckily, leaving the house is now optional, because your friends at Silver Oak Casino offer a comprehensive library of casino titles that are perfect for chasing that big win. Take advantage of a generous deposit bonus, and spin your way to one of the biggest jackpots in modern history. We’re looking forward to the chance to add you to this list!


Simon is an overactive gambler and the Staff Writer here at Silver Oak. He loves casino bonuses, online slots, and using the em dash too often. Currently, he rests his typing hands in Vancouver, Canada.