What “The Art of War” Taught Me About Gambling

by Jeff Harris
on January 30, 2018

For more than 2,500 years, a single work of literature has formed the foundation of mankind’s approach to strategic thinking: “The Art of War” by Sun Tzu.

In the service of King Helü of Wu, general Sun Tzu (which translates to “Master Sun”) commanded several military victories during the Warring States Period of ancient Chinese history. Written in the 6th century B.C., The Art of War contains 13 chapters of knowledge and insight gleaned from Sun Tzu’s firsthand experience devising wartime strategy.

Many conquerors have put their expertise on paper throughout the annals of time, from Nero to Napoleon, but Sun Tzu managed to imbue The Art of War with something more. The text has become timeless for many reasons, not the least of which is Sun Tzu’s ability to blend tactical guidance fit for the battlefield with philosophical teachings and reflections on a life well lived.

Aside from a stint in the Merchant Marines, I’m not exactly a military man, but I still have a dog eared copy of The Art of War on my nightstand. That’s because the wisdom of Sun Tzu seems to apply directly to my work as a professional casino gambler.

Just like Sun Tzu   well, maybe not just like him   I make my way in the world by analyzing situations designed to put me at a disadvantage (gambling games). And all the while, I’m forced to contend with an enemy that has made my demise their sole objective (casinos).

Success in Sun Tzu’s arena was defined by victory, but the threat of loss always loomed, and that holds true for casino gamblers. A properly employed strategy gave Sun Tzu the advantage over a better equipped force. Knowing this, I’m always looking for lessons in The Art of War that may be helpful in my enduring struggle against the house edge.

Fortunately, you won’t find many teachers as wise as Sun Tzu, whether you’re preparing an invasion or placing wagers at the casino. Below you’ll find 12 of my favorite quotes from The Art of War, along with a little insight into how Sun Tzu’s wisdom translates to the world of modern gambling.

Reflection

“If you know the enemy and know yourself, you need not fear the result of a hundred battles.

If you know yourself but not the enemy, for every victory gained you will also suffer a defeat.

If you know neither the enemy nor yourself, you will succumb in every battle.”

  Chapter III: Attack by Stratagem

This is probably the most well known quote from The Art of War, as it can be extrapolated to every aspect of life.

Just replace the word “enemy” with a goal you’re striving for, a habit you’re trying to break, or anything in your life that requires effort and exertion. Sun Tzu tells his followers to be introspective even while focusing on external issues, because without knowing yourself, you can never be truly prepared for the battle to come.

As a gambler, I tend to think of this quote like this:

I can work on my mathematical skills, memorize facts and figures, and build up my confidence   but none of that will matter if I don’t study specific games. Conversely, I can dive deep into the details of any given casino game, learning about pay tables, probabilities, and house rules   but it won’t make a difference if I don’t have personalized skills.

Mastering one game or another just isn’t good enough in the cutthroat casino industry, because setups, rules, and other factors are constantly changing. Along with game specific study, you should always take the time to solidify your base skills.

In doing so, you’ll achieve a balanced approach to combating the casinos that would make Sun Tzu proud.

Preparation

“Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win.”

  Chapter IV: Tactical Dispositions

For a warrior like Sun Tzu, the battle was won and lost before his soldiers ever swung a sword.

By preparing diligently for the clash to come, Sun Tzu simply planned and prepared better than his opponents. He took everything into account, from the issues he could control (formations, supply routes, and training), to the elements divined by fate (weather, illness, and shifting alliances).

As a result, Sun Tzu regularly defeated enemies who arrived to the fray boasting larger armies and other tactical advantages.

Translating the quote above to the casino, I see Sun Tzu advising players to put in their practice time before putting real money on the line. He didn’t have the advantage of the internet back in the days of Chinese dynasties, but if he did, you better believe Sun Tzu would be running simulations while preparing for every last contingency.

No matter what casino game you prefer, you should be able to find a free play version online somewhere. These might be offered by online casinos as a gateway to real money play, or through instructional resources like the Wizard of Odds website. Either way, these tools provide a perfect vehicle to practice casino game theories without the inherent risk of gambling with real money.

Victorious warriors win first, and successful gamblers do too, practicing proper strategy via simulator before stepping onto the casino floor.

Deception

“Appear weak when you are strong, and strong when you are weak.”

 Chapter VI: Weak Points and Strong

For decades before the Poker Boom of 2003, winning players earned the “hardest easy living in the world” by applying this single rule.

Legends like Phil Hellmuth and Johnny Chan pioneered a style of poker based on trapping their opponents. Techniques like the “slow play” may be standard stuff in the modern age, but before the boom, simply checking to feign weakness before springing your trap with a big raise was sneaky play. In fact, many of the older card rooms out there had house rules prohibiting the check raise altogether, due to its sheer effectiveness in separating suckers from their chips.

I love playing poker tournaments, and I suspect Sun Tzu would have as well.

In a tournament, all players begin on seemingly equal footing, with identical chip stacks to work with and starting hands dealt randomly from a shuffled deck. This equates to a battle between two equally staffed armies, with troop forces identical on either side.

But as Sun Tzu showed so many times during his military career, success isn’t based on the number of soldiers at your disposal – but the quality of those soldiers.

Give a good pro 15,000 chips to start, and double that to 30,000 for a “fish”   and I’d be happy to bet that the pro winds up with more chips by the end of the day. The pro knows how to disguise their strong hands by betting the same as they would on a bluff. Conversely, when they’re holding nothing but rags, the pro can stare straight through your soul while convincing everyone at the table they have the goods.

All is fair in poker and war – including the art of deception.

Tactics

“The whole secret lies in confusing the enemy, so that he cannot fathom our real intent.”

  Chapter V: Energy

This is another quote that speaks to the poker player in me, but it also applies to table game advantage play.

Obviously, for poker players, employing tactics designed to confuse your opponent is the entire objective.

You want them to put chips in the pot when you have strong hands, and to fold when you’re bluffing. Getting a stranger to follow your lead like that can be difficult enough, but when you’re both trying to take one another’s money, the game takes on an entirely different level of strategy.

I always go back to the classic “rock paper scissors” example to explain how this multilevel approach to strategy shakes out. If your opponent knows you like to throw rock, they’ll counter with paper, and knowing this, you should opt for scissors. But if your opponent knows you know that, perhaps they’ll adjust and throw rock themselves, in which case you should roll with paper.

And round and it goes…

The best poker players remember how certain situations went the first time, adjusting on the fly for that second encounter in hopes of confusing their mark. Like I said in the preceding entry, I wouldn’t want to play poker with Sun Tzu, as I expect he’d have me calling off value bets and blundering into ill timed bluffs with regularity.

As for the advantage play blackjack specialists out there, use Sun Tzu’s maxim to conceal your card counting and other techniques from the pit boss. The casino is always watching, after all, so it’s in your best interest to disguise your activity. Intentionally misplaying a hand or missing a bet on occasion is a great way to leave casino staff in the dark about your true abilities.

Focus

“In the midst of chaos, there is also opportunity.”

  Chapter II: Waging War

This quote speaks to me because I view the casino floor as the ultimate in controlled chaos.

Just think about it… Everywhere you look, the player is surrounded by elements designed to distract and deceive. Scoreboards hang above the roulette table, trying to bait you in by broadcasting streaks and patterns. Slot machines advertise massive jackpots with bright, bold signage, but you’ll only find the long odds against buried in the fine print. The craps table contains dozens of bets, almost all of them consigned to the “sucker” category.

The list goes on and on.

Casinos are a tough place to operate if you’re easily distracted by chaos, which is why the best gamblers out there tend be a focused bunch. Rather than wander the floor in search of the latest longshot wagers, these players simply stick to the script, grinding out a profit by beating skill based games.

The casino is chaos defined, and those who thrive amidst that disorder do so by focusing on the opportunities at hand.

Economics

“He who wishes to fight must first count the cost.”

  Chapter II: Waging War

It doesn’t take a genius to see how this pearl of Sun Tzu wisdom pertains to casino gambling.

In my line of work, bankroll management is by far the most essential skill that separates winning players from the rest.

Picture two players sitting side by side at a pair of video poker machines, each with $500 to work with. These players both have basic strategy for Jacks or Better memorized, and they’re both capable of recalling that information to play the game perfectly. Thus, aside from random variance, they should both perform equally over a set number of sessions.

Alas, one of these players likes to “take shots,” so they start betting $25 per hand at the high stakes. The other player sticks to $5 per hand betting, which is standard for his bankroll limitations.

By the end of the day, barring an incredible stroke of fortune, the big bettor is far more likely to go broke than his counterpart. Betting $25 per hand, or five percent of their total bankroll, doesn’t leave much room to survive the swings. But at the $5 increment, you’re applying just 1 percent of your bankroll on any given hand.

Before competing in any casino game, be sure to count the cost.

Rest

“There is no instance of a nation benefitting from prolonged warfare.”

  Chapter II: Waging War

At one point in my younger days as a blackjack sharp, I found myself sitting next to a man who seemed to have it all. He was well dressed, hand plenty of dough, and best of all, he knew blackjack like the back of his hand.

This guy played perfectly, and I mean that – every decision he made aligned with the tenets of proper strategy. He never deviated from the correct course of action, and as a result, he built his initial stake into a multicolored mountain of chips.

I had a decent night myself, so I colored up and cashed out after a few solid hours of grinding. When I did, the previously silent pro shot me a glance and asked “quitting time already?” He then told me that a good gambler never gets up when they’re running good, advising me to “play out my rush.”

I politely declined, heading back to the room to count my winnings and get some sleep. The next morning, I took a walk and wound up near the blackjack pit, where I saw the same man, sitting in the same seat and wearing the same clothes.

He had been there all night, trying to ride out that rush, but by now his former castle of chips lay in ruin. I hung around and watched him play out the last of it, only this time, he was making basic mistakes common to a blackjack rookie.

After a 24 hour session on the tables, even this blackjack savant slipped up and lost his way. Prolonging the battle may have seemed like a good idea at the time, but the choice backfired spectacularly.

Sun Tzu had it right all along, which is why I always recommend getting a full night’s rest before playing.

Discretion

“He will win who knows when to fight and when not to fight.”

  Chapter III: Attack by Stratagem

I think about this Sun Tzu quote every time I encounter a new side bet on one of my preferred table games.

I love to play Three Card Poker, and I enjoy the idea of an added jackpot element, so I was happy to see the Six Card Bonus side bet during my latest sojourn to Sin City. This optional wager allows players to combine their three card hand with the dealer’s three cards, in hopes of making their best five card poker hand.

Before betting on the Six Card Bonus, however, I decided to do a little research. As it turns out, this seemingly attractive side bet offers an absurd house edge of 15.28 percent – nearly triple that found on the double zero roulette wheel. In fact, the house edge was so high, only a few games on the casino floor (Big Six Wheel, keno, longshot bets in craps) were worse.

Armed with that knowledge, I became a winning player on the Six Card Bonus, simply by avoiding the bet at all costs. Knowing when to fight is important, but knowing when the battle won’t be worth your effort can be even more valuable.

Selectiveness

“In war, the way is to avoid what is strong, and strike at what is weak.”

 Chapter VI: Weak Points and Strong

This rule is simply an extension of the previous entry, but it bears repeating: don’t play games that aren’t player friendly.

Casinos rely on uninformed recreational players who don’t know a thing about odds and probabilities.

That’s how they’re able to get away with running Jacks or Better video poker using the inferior 8/6 (98.40 percent house edge) and 9/5 (98.45 percent) pay tables, right alongside full pay 9/6 machines (99.54 percent). Players who don’t know the score sit down and dump a $100, without ever knowing that they’re backing reduced odds.

Follow the advice found in The Art of War, and strike at what is weak (full pay games with higher house edge rates), while carefully avoiding combat with what is strong (inferior pay tables that favor the house).

Balance

“He will win who knows how to handle both superior and inferior forces.”

  Chapter III: Attack by Stratagem

With all of that said, I still enjoy the occasional spin on the slots or the roulette wheel.

I play these games of chance for fun, knowing full well that they offer higher house edge rates when compared to skill based options like blackjack or video poker. My goal as a gambler is always to win, but I also recognize the need for balance.

Trust me, grinding blackjack for 10 hours every day can be profitable for skilled players   but it can also be a slog. For all of its beauty, blackjack is based on a rote gameplay experience, more like a math formula than anything else. Take your hole cards, compare them to the dealer’s up card, and proceed according to basic strategy. Wash, rinse, and repeat…

After focusing intently on a game like blackjack, I find a few spins on a game of chance to be quite therapeutic. Call it blowing off steam, or getting away from the grind, but I consider these intermissions in my regular schedule to be useful over the long run.

Sure, I may give a few bucks back to the house by playing roulette, but those small losses are more than offset by the balanced mindset I bring back to the blackjack table. The trick is knowing how to handle the inferior gambles   playing short sessions and betting small   while you work to overcome superior games.

Savvy

“To win one hundred victories in one hundred battles is not the acme of skill. To subdue the enemy without fighting is the acme of skill.”

  Chapter III: Attack by Stratagem

Whenever I cash in a buffet voucher or free play coupon, this Sun Tzu quote comes to mind.

Casinos have plenty of ways to take your money, but they also offer tremendous opportunity to offset losses through the Player’s Club and similar promotions. Anytime you can score free funds from the casino, you’ve managed to subdue the enemy before the fight begins.

Generosity

“Treat your men as you would your own beloved sons. And they will follow you into the deepest valley.”

  Chapter X: Terrain

On a final note, Sun Tzu recognized the importance of treating his comrades well.

Gamblers should do the same, by tipping their dealers, chip runners, cocktail servers, and cashier attendants whenever the opportunity arises. If you’re a regular, it only takes a few tips to show the staff that you’re an ally to be valued.

From there, they might not follow you into any valleys, but they’ll be more than happy to comp your next meal or send you to a show on the house.

Conclusion

“The Art of War” is one of the most famous strategy books of all time. It’s not often associated with games of chance, but what the “Art of War” taught me about gambling shows you how you can use this classic to help you in your gambling ventures.

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