Signed by Kaplan: Our Favourite Blackjack Winning Streak

Michael Kaplan mickap September 2, 2019

Whether you are playing blackjack for $10 per hand or firing it up and risking $10,000, the feeling of being on a heater at the 21 table ranks among the greatest in gambling. The hits just keep coming and you can do no wrong. Splitting 8s against a 10? This mathematically correct play, which is invariably fraught with danger, just keeps going your way. Double down with a thin margin – say your 11 against the dealer’s King? You manage to snake through with a victory as if it is ordained to happen. The chips pile up and you break for daylight – enjoying the positive outcomes for as long as they can possibly last.

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Here are five players who each hit a run (or two), bet big and headed home with pockets bulging.


Hear the name Don Johnson and you either think of a pretty good actor or a bank-busting gambler with a stomach of steel. Right now we are talking about the latter Don. He had made a lot of money at horse racing and found out about alluring deals being offered to whales in Atlantic City. They were centered on games that featured favorable rules, large discounts (these are rebates on losses paid to big-money gamblers) and high stakes.

     Being the kind of guy who takes a shot only when he has a legal edge, Johnson put together a crew of talented advantage players who could assist him with things like card counting, hole carding and shuffle tracking. They ganged up on the tables and helped turn Johnson into a legend, transforming from Don Johnson to Don Fucking Johnson, as he likes to be called. “Beating Caesars [in Atlantic City] out of $4.23 million in 12- or 13-hours kicked things off,” Johnson tells me. “I ran really lucky, controlled the pace of the game and had great circumstances.” 

     Soon after, at the Tropicana, he won some $6 million and impacted the casino’s bottom line for that quarter.  How do you celebrate such a score? Johnson says that you don’t: “I go to my room and go to sleep. I’m usually tired.”


Dana White may be best known as the president of Ultimate Fighting Championship (the mixed martial arts league commonly called UFC), but, among pit-bosses and casino managers, he is regarded as a fearsome blackjack player with knock-out skills. So much so that that Palms in Las Vegas wants absolutely nothing to do with him at the tables.  He won $2 million from the casino and was asked to stop playing there. Then, somehow, the welcome mat was rolled out for him again. Finally, though, after taking down another $2 million, he’s been backed off for a second time.

    Acknowledging that this sort of heave-ho is the kind of thing usually unleashed on seasoned advantage players, White insists that looks are deceiving. “A lot of people are going to think I am a card counter…,” he told Las Vegas Review Journal.  “I’m the farthest thing from a card counter.”


Michael Geismer is president of Quantitative Investment Management, a finance firm that uses complex algorithms in order to profitably manage billions of dollars for its well-heeled clients. While in Las Vegas for a business conference, he decided to try his luck at blackjack.

     Geismer took out a marker for $10,000 and began to bet. Following the rules of a basic-strategy card – sold in casino gift shops, they provide correct plays for every blackjack situation; most amateurs cannot bear to follow them – he ran his 10 grand up to $460,000 by night’s end. A few more fortuitous sessions got him up to $710,000 in winnings – and that’s after leaving tens of thousands of dollars in tips. “I was definitely planning on playing.” Geismer told the Wall Street Journal. “I certainly was not planning on winning anything near that much.”


Casinos usually court and coddle celebrities who happen to be high rollers. Stars tend to lose money, often bring free publicity and attract the non-famous. Such is not the case for Ben Affleck at the Hard Rock Casino in Las Vegas.  He was asked to stop playing blackjack there. The request surely has everything to do with a winning streak that reportedly brought him $140,000 in one session and, one year later, another $800,000.

    Surveillance allegedly caught the actor card counting and was unimpressed that, following his first big win, he gave away most of his winnings by heavily tipping everyone from the dealers to the doormen. A bit disgruntled by the cold shoulder, Affleck told Details magazine, “Once I became decent, the casino asked me not to play blackjack. The fact that being good at the game is against the rules at the casinos should tell you something about casinos.”


The Australian media mogul Kerry Packer was know for making sky-high wagers at the blackjack tables – and recognizing when to quit. Casino bosses disparaged him as a hit-and-run player. But that did not seem to faze the late Packer, who passed away in 2005 and kept right on doing it until the end. In the process, he played as many as six hands simultaneously and wagered as much as $250,000 per hand.

     His jaw-dropping wins were rivaled only by his extreme generosity.  Word has it that he once managed to relieve the MGM Grand of some $20 million. Happy to share the wealth, Packer – who was supposedly worth in the neighborhood of $6.5 billion – reportedly gave out around $7 million in tips that night and slipped a cocktail waitress $85,000, which she promptly spent on a house.

    On another occasion, the high-rolling Aussie – nicknamed the Goanna, which is a jumbo-sized lizard from his homeland – managed to win 20 hands in a row with bets as high as $250,000 each. While an unnamed casino source once told me that, during the last 15 years of his life (from 1991 until 2006), Packer had dropped in excess of $20 million on the Vegas Strip, it did not make bosses comfortable with taking giant action from a man who accepted losses – including a $16.5 million hit at Crockfords in London – better than the casinos did. “Everyone finally said, ‘To hell with this guy,’” casino host Steve Cyr tells me. “They decided to keep him at 25 grand per bet.”

    Vegas executives were not the only ones who had trouble stomaching the mogul’s high rolling ways. An Australian politician criticized Packer for his unbridled gambling. Unimpressed, Packer fired back, “This is my money. I am entitled to spend it in any way.”


With four books (and more on the way) plus hundreds articles, Michael Kaplan is one of the most experienced writer in gambling related subjects.

He have covered big stories including famous gamblers such as Phil Ivey and Phil Hellmuth for publications including Wired, Playboy, Cigar Aficionado, New York Post and New York Times. Based in New York, where he regularly writes for the Post.

Read more about Michael Kaplan on his author profile.

About the Casinomir Writer

Michael Kaplan mickap
Author since August 30, 2022