The Biggest & Craziest Casino Bets Ever Placed

The Thrill of Betting It All

Every gambler dreams of the big win. But for a daring few, dreams weren’t enough; they pushed their chips to the centre of the table and went all in.

From high-rollers wagering millions to ordinary players betting everything they own, the history of casinos is littered with outrageous, record-breaking, and down right insane bets. Some ended in glory, others in disaster, but all live on as legends.

Let’s explore the biggest and craziest casino bets ever placed, and why these moments continue to captivate gamblers worldwide.

Set in a casino, a man dressed in a suit is standing exciting looking at his pile of pokere chips on a roulette table by his winning number 7

ASHLEY REVELL, WILLIAM LEE BERGSTROM, KERRY PACKER & ARCHIE KARAS

Ashley Revell – The Man Who Sold Everything

In 2004, Ashley Revell, a young Brit, made global headlines when he decided to sell everything he owned, including his clothes, and take the cash to Las Vegas.

·     Total bankroll: $135,300.

·     Casino: Plaza Hotel & Casino, Las Vegas.

·     Bet: He placed it all on red at the roulette table.

The ball spun. The crowd held its breath. It landed on red 7. Revell doubled his money to $270,600 in a matter of seconds.

Instead of pressing his luck, he cashed out and left.

Verdict: Revell’s story became a modern legend. It was reckless, brave, and crucially, he walked away a winner.

William Lee Bergstrom – The Suitcase Man

In 1980, William Lee Bergstrom walked into Binion’s Horseshoe in Las Vegas with two suitcases: one full of $777,000 in cash, the other empty.

He placed it all on a single bet at the craps table, the famous “Don’t Pass” line. The dice rolled, and he won.

·     He walked out with his winnings and disappeared.

·     Bergstrom returned several times over the years, making ever-bigger wagers.

·     His luck eventually ran out: in 1984, he lost $1million in a single roll.

Verdict: Known as the “Suitcase Man,” Bergstrom embodied the extreme highs and lows of big betting.

Kerry Packer – Australia’s Billionaire Rollercoaster

Australian media mogul Kerry Packer is perhaps the most feared and admired casino gambler of all time.

The Wins

·     Packer once won £7 million at a London casino in one night.

·     In Las Vegas, he was reportedly to have won $20–40 million in a single baccarat session.

The Losses

·     He just as easily lost it all, once dropping $28 million in a night.

·     Yet he was generous: during one winning streak, he tipped his dealers $1 million to share.

The Legend

·     Famously, when a Texan bragged in a Vegas casino that he was worth $60 million, Packer reportedly replied: “I’ll flip you forit.”

Verdict: Packer’s bets were so huge that some casinos refused to let him play. He was the ultimate high-roller, capable of bankrupting a pit in a single night.

Archie Karas – The $40 Million Run

No list of crazy bets is complete without Archie Karas. Arriving in Las Vegas in 1992 with just $50, Karas borrowed $10,000 and began one of the most astonishing streaks in gambling history.

·     In a matter of months, he turned that loan into $17 million.

·     At his peak, he had amassed $40 million, beating legends of poker and dominating casino games.

But his insane appetite for risk meant it didn’t last. By 1995, Karas had lost it all.

Verdict: Karas’s run is the stuff of legend — the ultimate example of wild gambling highs and lows.

CELEBRITY BETS (MICHAEL JORDAN, BEN AFFLECK & DRAKE), DON JOHNSON & OTHER FAMOUS BIG BETS

Celebrity Bets – Michael Jordan, Ben Affleck & Drake

Celebrities aren’t immune to crazy bets:

·     Michael Jordan – The NBA icon was notorious for gambling, placing six-figure bets on golf games, poker hands, and blackjack sessions. His competitive streak extended far beyond the court.

·     Ben Affleck – Known as a skilled blackjack player, Affleck reportedly won $800,000 in one night at the Hard Rock Casino in Vegas. His aggressive play got him banned for card counting.

·     Drake – The rapper has become the face of crypto casino gambling. On Stake.com, he livestreams himself betting millions on roulette, sometimes winning big, sometimes spectacularly losing.

Verdict: Celebrity gamblers don’t always match the pros for skill, but their crazy bets bring glamour and attention to the tables.

 

Don Johnson – Beating the House

Not every crazy bet ends in disaster. In 2011, Don Johnson, a professional gambler and race track executive, went on a blackjack run that stunned Atlantic City.

By negotiating favourable rules with struggling casinos, he was able to play with a razor-thin house edge. Over six months, he won $15 million without breaking any rules.

Verdict: Johnson’s story proves that sometimes the craziest bet is the one backed by brains.

Other Famous Big Bets

·     Charles De Ville Wells – A Victorian gambler who “broke the bank” at Monte Carlo in the 1890s, winning so much at roulette that the casino temporarily ran out of chips.

·     Patricia Demauro – In 2009, this New Jersey grandmother rolled the dice 154 times without losing at craps — a streak with odds of 1 in 1.56 trillion.

·     Nick the Greek – Legendary high-roller of the early 20th century, who once claimed to have won and lost half a billion dollars in his lifetime.

A man wearing a suit and open neck shirt sitting at a blackjack table in a casino celebrating his win
A image of a Daniel Craig lookalike sitting in a casino at a live dealer table, wearing a suit

FICTIONAL CRAZY BETS, THE PSYCHOLOGY OF THE BIG BET & THE BIGGEST AND CRAZIEST BETS AT A GLARE

Fictional Crazy Bets

Real life is dramatic enough, but Hollywood and literature have given us unforgettable fictional bets:

·     James Bond in Casino Royale, Daniel Craig’s Bond went all-in against Le Chiffre in a poker game with $115 million at stake. Fiction, yes, but pure high-stakes VIP.

·     Maverick (1994 film), Mel Gibson’s character goes all-in at poker in a Wild West show down.

·     Sky Masterson (Guys and Dolls), the smooth-talking gambler who bet on love as much as dice.

Verdict: Fiction exaggerates, but it draws from the experiences of real-life legends like Karas and Packer, blurring the line between myth and reality.

 

The Psychology of the Big Bet

Why do gamblers make these outrageous wagers?

·     Thrill-Seeking: The adrenaline of risking it all is as addictive as the win itself.

·     Ego & Reputation: For Packer, Karas, and Jordan, winning wasn’t just about money; it was about showing dominance.

·     Immortality: Win or lose, these gamblers became legends. Their names are etched into casino lore.

The Biggest & Craziest Bets at a Glance

·     Ashley Revell (2004): Sold everything, roulette bet on red. Won $270,600.

·     William Lee Bergstrom (1980s): $777,000 craps bet won; later lost $1m.

·     Kerry Packer (1990s): Won $40m in Vegas; lost $28m another night.

·     Archie Karas (1990s): $50 to $40 million streak, then lost it all.

·     Don Johnson (2011): $15m blackjack run, all skill.

·     Drake (2020s): Millions bet on crypto roulette.

·     James Bond (fiction): All-in $115m poker hand. Balls of steel!

You don’t need to sell everything like Ashley Revell or risk millions like Kerry Packer to feel the thrill of the casino. Today, you can enjoy the excitement safely and responsibly, from the comfort of your own home. Play at Trusted UK Online Casinos.

www.casinojester.co.uk
A group of friends watching a poker chip fly through the air at a live dealer games table in a casino setting

OVERVIEW

The biggest and craziest casino bets in history remind us why gambling is so captivating. Whether it’s Ashley Revell risking everything on one spin, Kerry Packer casually wagering millions, or James Bond battling villains at the poker table, these stories combine glamour, drama, and sheer audacity.

Most of us will never bet millions. But that’s the beauty of these legends: they inspire, entertain, and remind us that in gambling, as in life, fortune favours the bold.

Choose one of the online casinos from our approved list, grab your bonus, and start playing smarter today.

www.casinojester.co.uk

CJ Casino Guide

Beginner's Guide to Casinos

CJ Craps Guide

Beginner's Guide to Craps

CJ Poker Guide

Beginner’s Guide to Poker

CJ Blackjack Guide

Beginner's Guide To Blackjack

CJ Roulette Guide

Beginner's Guide To Roulette

CJ Baccarat Guide

Beginner's Guide To Baccarat

10BET CASINO OFFER
100% UP TO £50 ON
FIRST DEPOSIT

Operator Monthly Bonus Banner

Top Features of UK Online Casinos

Playing at our recommended casinos offers an exciting and secure gaming experience. Enjoy generous online casino bonuses, a wide variety of gaming options, and robust security measures.

UK Gambling Commission Logo with a white background and the union jack flag

UK Regulated, secure & trusted

A large variety of different online casino games displayed across the image

Huge variety of games, jackpots, free spins & bonuses

An 18+ symbol in a red circle on a white background

All casinos offer Responsible gambling tools

A list of payment methods such as Google pay, Apple pay, Visa, Mastercard and PayPal

Fast, safe & simple deposits & withdrawals

A 5 star customer service satisfaction rating with a man smiling at his mobile phone in the background

Good Customer Service

A laptop open, on the screen there is a roulette wheel with poker chips and cards flying out across the image on a black background with a gold fire effect behind the laptop

Clear & simple design to ease usability

Trusted by top brands in the industry