10 Record-Breaking Wins and Losses in Gambling History

Gambling history is packed with jaw-dropping moments, from wild wins to brutal bankroll wipeouts. Here are ten legendary stories that show how unpredictable fortune can be—sometimes you’re on top of the world, other times you’re handing over the keys to your legacy.

1. The Mirage Jackpot That Shocked Vegas

In 1989, a 76-year-old WWII veteran hit a $4.6 million jackpot at The Mirage in Las Vegas—an unheard-of sum at the time. It wasn’t just life-changing, it was casino history in the making.

2. Lightning Struck Twice

That same veteran wasn’t done yet. In 2005, at the ripe age of 92, he pulled off another miracle—this time pocketing a $21 million win. Talk about retirement goals.

3. FedEx’s Last Roll of the Dice

When FedEx was on the verge of collapse in 1973, founder Frederick Smith made a bold move—he took the company’s last $5,000 to Vegas and turned it into $27,000 playing blackjack. Just enough to keep the planes flying a little longer.

4. Archie Karas: From $50 to $40 Million… Then Back to Zero

Between 1992 and 1995, Archie Karas pulled off the most insane streak in casino history, flipping $50 into $40 million through poker, dice, and pool hustling. But luck, as always, had the final say—he lost it all within a few years.

5. The Biggest Online Slot Win Ever

In 2013, a Finnish player casually logged into an online casino, spun the reels, and walked away with €17.8 million (about $24 million). That’s the kind of “check your emails later” moment we’d all like.

6. Kerry Packer’s Costly Three Weeks

Australian media mogul Kerry Packer made headlines in 1995 for losing a staggering $28 million during a three-week gambling binge in London. For most, that’s devastating. For Packer, it was a scratch on the surface of his empire.

7. The Megabucks “Curse”

Las Vegas folklore warns of the Megabucks Curse. The most famous tale? A cocktail waitress who won nearly $35 million in 2000 and then suffered a string of personal tragedies. True curse or coincidence? You decide.

8. A Heritage Lost in Australia

In 1999, a Japanese businessman reportedly lost around $127 million in Australian casinos. It remains one of the largest individual gambling losses ever and a stark reminder that the house usually wins.

9. Don Johnson’s Blackjack Blitz

In 2011, pro gambler Don Johnson didn’t just beat the house—he schooled it. Over six months, he took home more than $15 million from three Atlantic City casinos, all thanks to clever negotiation and flawless play.

10. All-In on Red

Ashley Revell went all in—literally. In 2004, he sold everything he owned, walked into a Vegas casino, and bet his entire $135,300 net worth on a single spin of the roulette wheel. Red came up. He walked away with double his money and a great story.