Playing blackjack for cash, online or off, you are going to encounter incredible runs of luck and loss. You can employ a card counting system perfectly, and be staring at an amazingly positive running count of +9, make a huge bet, and lady luck might just decide to take your money and run. Or you can sit down and play without any basic blackjack strategy, make all the wrong moves, and win a dozen hands in a row. If you play black jack long enough, you will see just about everything happen. And if you do not want to take my word for it, check out the most memorable blackjack win and loss recorded by a man who is regarded as probably the best professional blackjack player of all time.

Tommy Hyland was one of the first seven 21 players selected by professional gamblers into the Blackjack Hall of Fame, and he has a computer for a brain. Well known for winning many millions and training other players to count cards effectively, he has a lifetime of incredible blackjack memories. When this King of Blackjack tells you that a particular win was his most memorable, you know you are about to get a great story. In the mid-80s in Atlantic City, Hyland was working on what he called a massive project involving two dozen or more players. The team would hunt down and exploit dealers who shuffled in a particular way. The strategy also involved playing heads-up with very high stakes, but the team had to find a dealer that offered an attractive situation first, turning the blackjack odds in their favor.

To get a table to himself, several of his teammates smoked foul-smelling cigars, acted rudely, and even "accidentally" spilled drinks on players to get them to leave a table so Hyland could go heads-up with a particular dealer. Sometimes the particular strategy he and his team members would employ would take hours to put into play, only to see Hyland stare at a cold deck all night, presenting little or no opportunity at a winning session. One night, a certain blackjack dealer, who did not even know he was shuffling in a way that could be exploited, was a very large man nicknamed Rosie. And on this particular night, the fickle nature of lady luck was kind to Mr. Hyland and his team of professional blackjack players.

After working so hard and diligently for several hours, Hyland was able to win more than $140,000 from Rosie. The dedicated blackjack pro said that years later he returned, only to find Rosie right back at the same table where he left him, dealing the same way. It was not the size of the win that made this session memorable, but rather the incredible coordination of teamwork over an extended period of time that the King of Blackjack says ensures he will never forget the victory. But even the biggest winners eventually lose, which leads us to the most memorable black jack loss of this otherwise successful professional's career.

In the early 1980s, Hyland hooked up with four astute individuals and became a shuffle tracker. This was at a point when he had already established himself as a successful blackjack pro, simply using standard card counting techniques. He thought that adding shuffle tracking to his card counting regimen would make him impervious to loss. That was not the case. At the Fremont in downtown Vegas, in a span of less than a week, Hyland managed to lose $100,000. He was well known at the time, and while the Fremont management was ecstatic about taking such a substantial amount of money from a known card counter, Hyland says they appeared puzzled that he was at their casino rather than some ritzy spot like the MGM or Caesar's Palace. Hyland said the loss taught him a valuable lesson – even if you have all the odds stacked in your favor you can still lose, so cut your losses when things are not going your way, and live to play another day.

Anyone can win and anyone can lose, even when employing perfect blackjack strategy. The cards don't care if you are counting them or not, five, six and seven deck shoes are frequently shuffled, and even when you get on a winning streak, your table can go colder than a polar bear's behind in an instant. Card counting, intelligent bankroll management and other techniques will always give you the best possibility at winning when you play 21, because the nature of the game gives you more control than almost any other casino offering. But never forget that even the best brains in blackjack experience memorable wins and losses, and that any time the fickle finger of fate is involved, anything can happen.

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