11 of the biggest losses casino dealers have ever witnessed. #7 – $209,000 blackjack loss. “A college kid bet his entire net worth on a hand of blackjack on graduation weekend with his friends watching. It was under $15k, but it was literally every cent the. Blackjack side bets are based on chance, offer a chance of a very big payout, and the house edge is greater than it is for the main game of blackjack. First and foremost, blackjack side bets are fun and they can break up long boring blackjack sessions as well as offer a chance of a big payout. In Felt’s variation of Buster Blackjack, the biggest prizes drop when the dealer busts with at least 7 or 8 cards against a player blackjack. Examine the rest of the payouts below. An 8+ dealer bust while the player has a blackjack offers the mind-blowing payout of 2,000 to 1.

The famous card game known as blackjack has rocked the gambling world for centuries. Surely, people have lost a lot over it, but there were a lot of lucky winners over the years as well. The reality of it all is that probably some of the biggest wins haven’t been made public and will forever remain a secret between the player and the dealer, especially big wins from previous decades when there was no internet, no smartphones and no ever present media.

But just for fun, what are the biggest wins known in blackjack and who were the lucky players? Here are the top five.

No.5: Shoeless Joe

We have a mysterious case of a winner whose identity was never revealed. As is turns out, it was an elderly man known as the Blackjack bum or Shoeless Joe (not related to Chicago White Sox player). He was believed to be kicked out of the house by his wife and was evidently not taking care of his personal hygiene for a while.

He came into the Treasure Island casino in 1995, without any shoes on his feet, and sat at a blackjack table after cashing in his $400 social security check. The man was ignorant to basic blackjack strategy, splitting 10s and doubling down on hard 12s and hard 13s, but that week he managed to win around $1.5 million. However, it must have triggered his unpleasant side, as he became aggressively annoying, which gave casino management reason to rejoice when he finally lost and was thrown out of the casino.

No.4: Ken Uston

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Blackjack Hall of Fame member Ken Uston was a complete opposite from our previous winner. Relyig on Edward Thorp’s Beat the Dealer book, he based his play on strategy, rather than pure luck, mastered the mathematical elements of the game and applied them on team play.

He is referred as the creator of blackjack card counting teams, early predecessor of the notorious MIT team.

Between 1975 and 1981, Ken Uston and his team of card counters accumulated winnings resulting in a sum worth more than $4.5 million, running the impressive streak across multiple tables and numerous casino venues across the United States. Check our Blackjack History Infographics for more info.

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No.3: Kerry Packer

Our next contestant is the famous Aussie millionaire Kerry Packer. He was a media magnate, with a reputation of a passionate gambler – and was always considered one of the highest rollers in casinos worldwide. In 1991 he was sitting at a public blackjack table of the Las Vegas Hilton casino. It didn’t take him much to win $7 million for that one night. Apparently, the Hilton had a special private room made for him after that. When he came back the next year, he reportedly gave back $10 million to the casino, but he probably didn’t regret the loss all that much.

No.2: Don Johnson

One of the wins that set on fire the gambling world was certainly Don Johnson’s accomplishment in 2011. No, we are not talking about the famous ‘Nash Bridges’ Don Johnson, but it was also a pretty resourceful man, a CEO of Heritage Development LLC company. He had an unbelievable winning streak from December 2010 to April 2011, earning a total of $15.1 million playing in several major Atlantic City casinos.

The successful blackjack player first won $4.23 million at Caesars Atlantic City, then $998,000 at Borgata Hotel Casino & Spa the same month. After a while, his luck struck again, big time. He won $1.8 million at Borgata again, and in two nights another $2.25 million. And lastly, he won $5.8 million at Tropicana Casino.

As he claims, he didn’t count cards apply any other technique. He simply took advantage of every favorable house rule there is, and won more as he played more. According to some interviews, he managed to negotiate a certain discount on his loses in order to keep playing, and it certainly paid off.

No.1: Kerry Packer

It’s not a mistake. We simply have to mention Kerry Packer once again. Not just because we want to, but because the man has had an extraordinary gambling career.

After becoming a regular at Las Vegas whenever he had time off or was on holiday, he came back for another round in 1995. Packer was reported to have played up to 8 hands simultaneously at multiple blackjack tables at Las Vegas MGM Grand this time. He placed bets of $250,000 per hand, and 20 times in a row there were only winning hands for him.

Within 40 minutes he finished his blackjack session cashing out $20 million. Allegedly, he renounced $1 million in favor of the dealers, leaving it behind as a tip!

The world of blackjack is truly inspirational, wouldn’t you say?

The history of gambling is littered with examples of people dropping unthinkable amounts of money on things as trivial as the toss of a coin or a single roll of dice. Despite stories of such wanton excess, including many of individuals winning or losing tens of millions of dollars in a single night, discerning which of these high-rollers holds the honor of making the largest single bet in history is rather difficult. This is in part because casinos and bookmakers tend to keep information about especially large bets close to their chests. For example, prior to the 2018 Super Bowl, it was reported by the MGM Grand in Las Vegas that an unnamed gambler had placed, to quote, “one of the largest reported bets… in Nevada”, wagering that the statistical underdogs, the Philadelphia Eagles, would beat the spread. The problem was that while MGM’s vice president of race and sports, Jay Rood, was happy to report that the bet was amongst the largest Vegas had ever seen, he refused to specify exactly how much the anonymous gambler had actually wagered or who had placed the bet. The same is true of similarly large bets placed in recent years with casinos and bookmakers being frustratingly opaque when it comes to reporting the exact amount especially brave or wealthy gamblers wager on sporting events and the like.

All this said, the nature of high-stakes gambling and the kind of personality that tend to gravitate towards it means that there are countless stories out there detailing frankly astonishing displays of testicular fortitude.

As for a few of the largest of such single bets we could track down, consider the story of William Lee Bergstrom, better known more simply as the Phantom Gambler before his identify was later discovered. In September of 1980, Bergstrom casually strode into Binion’s Horseshoe Casino in Vegas carrying $770,000 (about $2.6 million today) in cash in a suitcase. He subsequently walked over to craps table and explained that he’d like to bet it all on a single throw of dice- a wager it should be noted that represented, at the time, the single largest well documented bet ever placed in the United States. After a few nervous glances were exchanged between the croupier and the pit boss, casino owner Ted Binion intervened and told Bergstrom that the casino would of course honor the bet and personally walked him over to the cashier’s cage to have his money converted into chips. You see, at the time Binion’s had a policy that if it was a gambler’s first visit to the casino, they’d honor a bet of any size and Ted Binion wasn’t a man who was want to go back on his word.

As promised, Bergstrom took the chips and bet them all on a single throw of dice, which he won. Bergstrom then walked back over to the cashier’s cage and had all his winnings converted back into cash, which he then divided between the original suitcase his money had been stored inside of and an empty suitcase he’d seemingly brought along just in case he won.

Binion would later recall that he personally escorted Bergstrom to his rental car and observed him nonchalantly throwing the suitcases onto the passenger seat before driving away. During the entire ordeal, Bergstrom barely spoke and reportedly reacted to the news he’d won the equivalent of $2.6 million today with nothing more than mild surprise. Because he never told anyone his name and the bet had been so astonishing, Bergstrom came to be known in Vegas as the Phantom Gambler as well as, perhaps more aptly, the Suitcase Man.

Things got even more curious when, in 1984, Bergstrom once again walked into Binion’s and did the exact same thing, this time betting $538,000 (about $1.3 million today). As before, Bergstrom bet the entire amount on a single throw of dice (which he again won) and left the casino without acknowledging what he’d just done or really speaking to anybody outside of the minimum needed to make the bet and cashout.

A few months later, Bergstrom strolled into the casino again and bet one million dollars on another single throw of dice. On this occasion, however, Bergstrom lost but still somehow maintained his cast-iron facade, reportedly afterwards simply eating an enchilada and leaving. A few months after that, Bergstrom killed himself.

Although it was initially reported that Bergstrom killed himself because of his gambling losses, a letter written by Bergstrom prior to his passing revealed that he was left despondent by the breakdown of a relationship he’d been having with a younger man. In the wake of his suicide, family members revealed that Bergstrom wasn’t a big gambler and nobody who knew him personally seemed sure why exactly he’d randomly bet such large sums on something as trivial as a single throw of dice. You see, independently wealthy from real estate dealings in his native Texas, Bergstrom had no need for the money he won, though he did enjoy travelling the world with his lover prior to their breakup.

Bergstrom’s brother would later surmise that he had made the bets in an attempt to be remembered for something. The latter hypothesis was supported by the fact that Bergstrom’s will specified that his urn bear an inscription identifying him as the “Phantom Gambler of the Horseshoe, who bet $1 million on November 16, 1984”.

Moving onto something a little less depressing, another gambler known for making exceptionally large bets, seemingly on a whim, was Australian media mogul and billionaire Kerry Packer. Legendary in the sphere of gambling for his exploits, Packer happily gambled away millions during his lifetime, routinely betting hundreds of thousands of dollars on single hands of blackjack or a game of baccarat, and over the case of days of gambling winning or losing sometimes tens of millions of dollars.

Known for his eccentricity and generosity, Packer would casually hand out six figure tips and liked to reward especially attentive waitresses and croupiers by paying off their mortgages. The billionaire was so well known for this that during his lifetime a popular adage amongst casino workers in Las Vegas was that “nobody called in sick when Kerry Packer was in town”. On one occasion, Packer attempted to tip a croupier $80,000 who explained to him that because all tips had to be pooled, she would only get a small portion of it. A furious Packer, who by the way was also known for having a bit of a temper, called over the casino’s owner and demanded that he fire the girl on the spot. Not wanting to lose the casino’s best customer, the owner did just that, at which point Packer handed her the $80,000 and demanded the owner rehire her.

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On another occasion, in 1990, Packer was taken ill and needed to be rushed to hospital. Not long after, each of the ambulance crew were given $1 million for their services. On yet another occasion, upon learning that casino staff had lost out on a $40,000 bonus because he’d won too much money, he tipped the entire staff $1.3 million.

Gambling wise, Packer constantly hassled casinos into letting him make bigger and bigger bets, sometimes calling ahead to ask how much money a given casino had on hand before turning up. If the amount wasn’t to his liking, he’d simply take his business elsewhere. Packer’s habit of making obscenely large bets coupled with his tenacity and skill led to him quite literally running a few casinos out of business during his lifetime, with Aspinall’s in London reportedly going bankrupt directly as a result of Packer winning so much of their money in 1990. This led to Packer being banned from dozens of smaller casinos and a few big ones- a fact he was especially proud of, once reportedly responding to being politely asked to leave a London casino by saying “I’ve always wanted to be banned from a casino for winning too much.”

It’s unclear what Packer’s largest single bet ever was, with some reports suggesting that the aforementioned MGM Grand allowed him to play blackjack for as much as $500,000 a hand shortly before banning him for life after he won $26 million in a single evening of gambling.

However, if a popular anecdote about Packer is true, it would seem likely that he made the single largest wager in history, or at least seriously proposed wager. The story goes that while enjoying some high-stakes gambling at a private table at the Bellagio, Packer was approached by a Texas oil tycoon who asked if they could join him. Packer politely refused, prompting the irate Texan to loudly boast that he was worth, depending on which source you consult, anywhere between $60 to $100 million. Packer, woefully unimpressed by the taunt, looked the Texan dead in the eye and said “If you really want to gamble, I’ll flip you for it.” The Texan, however, declined to bet his entire fortune on one single flip of a coin so the bet was never consumated.

So is that story actually true? Well, for what it’s worth, it has been independently confirmed by multiple sources including Mirage Resorts CEO Bobby Baldwin who claims to have personally witnessed the exchange. If true, we feel fairly confident that Packer likely holds the record for largest bet ever seriously proposed, though not placed or won.

Of course, Packer was worth billions. So even $100 million wasn’t exactly going to change anything about his lifestyle if he lost or won. This brings us to the honorable mention for the most ballsy bet of all time, which happened to also be a rather large one, at least by most people’s standards.

Enter then 32 year old Ashley Revell. Although Revell’s bet was for a comparatively paltry £76,840 (roughly $180,000 today), the amount represented every penny he had to his name. You see, in addition to clearing out his savings, Revell sold all of his possessions down to the shirt off his back (he made the bet in a rented tuxedo). In other words, outside of perhaps the value of his underwear, assuming he was wearing any, Revell was quite literally betting everything he had.

While there are many stories of people gambling away their every possession, even the wealthy (such as that time a guy took $50 and turned it into $40 million via gambling, then promptly lost it all), there are no examples we’re aware of of someone doing so on a scale like this via a single bet. Likewise, as impressive as it is to read about someone betting half a million dollars on a single hand of poker or something, a billionaire betting that amount is about the equivalent to a normal person putting a dollar into a slot machine. Win or lose, is just isn’t really risking anything for the person and, if they’re not risking anything, can it really be called gambling?

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Revell, on the other hand, bet everything on one, single spin of a roulette wheel- a feat even a man like Kerry Packer never dared in a lifetime of gambling.

So what happened? He bet it all on red and won, managing to double his money on one spin, giving him roughly the equivalent of $360,000 today.

He admitted after the experience that, “… it was a mad thing to do. And I’m thinking back now about what would have happened if I lost. I’d have had nothing to go back to, nothing to wear. But I’d still have my friends, my family, and they’d always be there for me. So they gave me the security to be able to do this.”

Unlike many who win big in gambling, Ashley decided that tempting fate once was enough for him. He declined to bet a second time and cashed in his chips at the table and walked away.

As for what happened after, Revell spent a small portion of his winnings on a motorcycle trip around Europe, where he met a girl while in Holland. He states, “I took her back to England with me, we married and now we’ve got two children. You could say I have my bet to thank for finding me a wife.”

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So, if you think about it, while he didn’t know it at the time, that single bet wasn’t just for his entire net worth, but he was also gambling his wife and the lives of his two children, the latter of which would have never existed had he lost.

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