Top 10 Biggest Wins in Blackjack Throughout History

Blackjack is arguably one of the coolest casino games ever invented. With a history of over 400 years, blackjack has reinvented itself with a newer & better iteration, and in each century, there have been casino players who have mastered the technique of getting the better of the house and winning big. 

The list I’m about to present to you features some of the biggest blackjack winners, who have managed to etch their names in the history books by winning ludicrous amounts of money and getting insanely rich in the process. 

So strap yourself in as I take you through time and introduce you to the top 10 biggest blackjack wins, ever. 

1. Kerry Packer, The Man, The Myth, The Fearless Gambler

Bet Won: $24 – $33 million (₹170 – ₹230 Crores)

Kerry Packer

Image Source

A billionaire from Australia, Kerry Packer was the enthusiastic gambler who everyone loved and the casinos feared. Before his death in 2005, Packer is known to have brought the profits of wealthy casinos down substantially by winning insane bets while playing a game of blackjack

Winning somewhere around $24 to $33 million in the MGM Grand, Packer aced (no pun intended) both in blackjack & baccarat. Sources mention that this led to the firing of a handful of MGM’s employees who allowed him to make such huge bets. 

Worth nearly $7 billion, Packer was the richest man just before his death in 2005, and his glory days of gambling also were these years just before his passing. 

This media Moghul is said to have placed several bets between $250,000 and $300,000 simultaneously and never bothered to have lost in millions. 

Legend says that when a well-known oil tycoon from Texas ran his mouth at Packer in a casino and said, 

“You know who I’m partner? I’m worth $60 million!” 

Packer then pulled a coin out and responded, “I’ll flip you for it.” 

You can tell that Kerry was pretty a character and his legend still lives on in the stories told in casinos, even after 15 years of his passing. 

2. The Unsolved Mystery of Shoeless Joe

Bet Won: $1.5 million (₹11 Crores)

I have to admit, this story is a spooky one but yet, a blackjack legend on its own. A man who was kicked out of his own house by his wife walks into a casino with no shoes on, with a security cheque of $300 and ends up winning a massive bet of $1.5 million

Defying all the strategies of blackjack by doubling when he shouldn’t have, splitting when other professionals wouldn’t, Joe caught an extremely lucky break on this auspicious day.  The identity of this mysterious yet impressive personality is still unknown even today. 

3. Bill Kaplan’s MIT Blackjack Team

Bet Won: $50 – 100 million (₹350 – ₹700 Crores)

Bill Kaplan’s MIT Blackjack TeamImage Source

If the name Bill Kaplan or a team of MIT students winning big at blackjack rings a bell, it’s because there was a fully-fledged movie made about this notorious team of geniuses. 

Starring Kevin Spacey, the movie “21” does a pretty great job of explaining how the card counting technique and a sliver of luck helped the MIT grad students break casinos and win anywhere between a whopping $50 to $100 million altogether. 

Utilizing the basic form of card counting which involves assigning point values to cards and decks of cards played in a casino, the team observes the shoe size the cards were stored in and then added & subtracted the values assigned to each card they were hit by the dealer. 

4. Dana White, The Undefeated Blackjack Champion

Bet Won: $7 million (₹50 Crores)

Dana White

Image Source

Little did you know, the infamous, charming president of the Ultimate Fighting Championship (UFC), Dana White has been a gambler and a blackjack player, much earlier than he became the president of the UFC. 

Having had a knack for the game, Dana has won in millions, quite a few times in the last decade, but his infamous feud with the Palms Casino in 2012 stands out.

Placing regular bets of around $25,000 a hand, Dana was one of the Palms high rollers and the UFC events held in this casino for 15 straight years stand testament to their relationship.

But after winning a few million dollars, back to back, the relationship between them crumbled. 

Cutting his credit in half and limiting his bets at the tables to a maximum of $5,000, per hand, The Palms Casino made Dana extremely furious and he immediately cut cords with them and moved the 16th UFC finals to the Hard Rock instead. 

Dana White has won an impressive $7 million in a single night and therefore earns a rightful place in this list of biggest wins in blackjack history. 

5. Ken Uston, The Math over Luck Mantra

Bet Won: $4.5 million (₹32 Crores)

Ken UstonImage Source

The book titled “Beat the Dealer” authored by “Thorp” changed the life of Ken Uston in the late 1960s and turned him into a highly skilled blackjack player. 

Winning more than $4.5 million during his glory days, Uston’s close examination of the game, mathematical prowess, and meticulous analysis always helped him win big. 

Known as “a genius card counter”, his card counting capabilities were picked up by casinos and he was immediately banned from playing at several of them at Nevada for some years. 

It is said that several casinos started to boost the multi-hand blackjack as well as changed many card deck shoes to discourage card counters who were inspired by Uston. 

6. Don Johnson, The Daring High Roller

Bet Won: $15 million (₹110 Crores)

Don JohnsonImage Source

A professional gambler, businessman, a former corporate executive, Don Johnson is on this list for beating the casinos in Atlantic City for over $15 million in a span of 6 months in the year 2011. 

The CEO of Heritage Development LLC, Don’s win is known as one of the biggest wins in blackjack history. 

An infamous event Don took part in was a 12-hour long marathon at the Tropicana Casino & Resort Atlantic City, where he won 3 consecutive hands and took home $1.2 million. 

He was so fixated on splitting the bets that on one occasion, he had bet $100,000 which was dealt with two eights, which he split, and another two eights came his way, which he ended up splitting as well. 

Don says that the bans have not affected him much as he still plays blackjack with his planned recklessness and in recent years, he has been spotted partying with the likes of Pamela Anderson and Jon Bon Jovi. 

7. Michael Geismar, Making it Rain, Professionally and Personally

Bet Won: $710,000 (₹5 Crores)

Michael GeismarImage Source

The saying “rich gets richer” holds extremely true to Michael Geismar’s case more than anyone else in this list as his mere presence in a casino, at the right time, made him richer than he had anticipated. 

A hedge fund investor by trait, Michael was at the Bellagio Casino in Las Vegas for a 3-day hedge fund conference, and just turned lucky one fine morning. 

In the search of a little distraction and morning breakfast, Michael stumbles upon a blackjack table and lays down a measly $300 bet, and by the time you could snooze, boom, he had turned it into a massive win of $470,000. 

After losing a few sessions the next couple of days, just before the conference ended, Michael won big by laying bets of around $10,000 and piled up a massive jackpot of $710,000. 

He was later documented saying:

“I was definitely planning on playing; I certainly was not planning on winning anything near that much.”

8. Shane Smith and the $300,000 Dinner

Bet Won: Unknown

Shane Smith

Image Source

A wealthy media businessman who is visiting Las Vegas for the annual Consumer Electronics Show (CES) throws an extravagant, unplanned $300,000 dinner for his close ones. Sounds crazy? 

Yes, this indeed happened when Shane Smith, the CEO at Vice Media won big while playing blackjack at MGM Grand casino in Las Vegas, he went on to throw a feast for 25 of his closest friends & family. 

What’s even more insane than this? Until today, no one knows exactly how much money Shane won playing blackjack that evening for him to throw a $300,000 dinner. 

People present during the game confirm that Shane won at least $100,000, which pales in comparison to the final amount he may have won.

9. Ben Affleck, the Actor & the Busted Gambler

Bet Won: $800,000 (₹5.7 Crores)

Ben AffleckImage Source

Popular movie star, director, and award-winning writer, Ben Affleck found his love for gambling in the form of blackjack. 

Known for his huge win of $800,000 while playing at the Hard Rock casino in Las Vegas, Ben was deeply in love with blackjack and was learning the ropes of it while he was caught. 

Ben was busted by the dealers and the security for the very reason. Playing along with his buddy Matt Damon, Ben had played 3 simultaneous hands at $20,000 apiece before he was asked to stop.

Tipping the waiters, the door boys, and the dealers more than $5,000 per person, Ben gave away around $140,000 out of the $800,000 he had won, and this just shows that the Batman actor was there to get better at the game of blackjack and not to patronize or cheat the house. 

10. Goksel Selay, The Lucky Cabbie

Bet Won: £90,000 (₹84 Lakhs)

Goksel SelayImage Source

Talk about dreams coming true, no, literally. Goksel Selay, a cab driver from the UK had a dream about getting rich and winning money and so he did, in real life. 

After playing blackjack at Genting Casino Club Westcliff in Southend, United Kingdom, Goksel won a handsome £90,000, as the night was quiet for the cab driver and he just wanted to test his luck. 

A casino that links 35 other casinos worldwide, Goksel was dealt 4 aces and the jackpot for which is £89,950, and post winning, he had the following to say:

“I could not believe it, it’s the first time in my life I have had such a big win. I don’t usually play blackjack as I prefer roulette but I wasn’t having much luck there so I decided to play blackjack instead as I saw the jackpot was rising”. 

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