Three Object Lessons in Playing Blackjack

by J. M. Pressley
First published: December 30, 2007

Mistakes in blackjack can cost you. Here are some lessons in making your bankroll last longer.

I've made nearly every mistake there is to make playing blackjack at some point or the other. Fortunately, a great many of them have been made in the safe environment of Hoyle's Casino on my PC. After all, it hurts a heck of a lot less to lose a C-note when it's all make-believe and you have a starting bankroll of $5,000 in pretend chips to toss around. But I've learned some hard lessons with real money at stake along the way as well.

On the surface, blackjack is a relatively easy game to understand. You square off against the dealer, and the closest to 21 without going over wins. It gets a bit more complicated when you start considering situations like splits, insurance, doubling down, etc. And that's where it has taken me more time than I'd care to admit to get any good at blackjack. By that I mean that it will take more than a half hour for the casino to relieve me of my bankroll.

I'm by no means a compulsive gambler. I've never bet money I couldn't afford to lose, and I rarely find myself in a casino more than a couple of times a year. However, I find blackjack mildly addictive since a shoe can play pretty quickly, and I have this unfounded competitive optimism that any losing streak is only a hand away from reversing itself. Compounding the risk of the situation, for the first 35 years of my life, the only guideline of blackjack I ever consistently followed was to never hit on 17 or above. So, to sum up: competitive streak plus utter lack of strategy equals object lessons in humility.

Lesson 1: How to Lose $100 in Four Hands

A few years ago, I visited the Harrah's Casino in Indiana with a good friend of mine. I decided that this was the night I was actually going to sit in at a blackjack table at a real casino. See if you can spot all the mistakes in this case study: while my buddy veered off to play Pai-Gow Poker, I went off on my own, picked a $25 table to sit down at, and proceeded to play with no inkling of even basic card strategy.

To say that the next four hands went badly would be an understatement. I was dealt a hard 12 on the first hand, drew a king, and busted. The next deal was a 17; the dealer flipped a 19. When I drew a 20 the next hand, I was smug until the dealer drew two cards to make 21. That alone irked me enough to throw more good money after bad, and I remember getting dealt a 15, hitting—I can't remember what up card the dealer was showing at that point—and busting. That was four hands in approximately three minutes and $100 of the easiest money that Harrah's made that night. The tone was set; I blew through my entire $250 bankroll in under an hour.

The moral of this story is twofold: don't get in the pool if you don't know how to swim, and certainly don't go it alone. Use the buddy system to help keep you from doing anything blatantly stupid (like putting money down on a $25 table when you don't really know how to play).

Lesson 2: Know When to Cash Out

That little experience at Harrah's put me off of casino blackjack for nearly two years. That ended with a trip to Vegas. While staying in Caesar's Palace, I found myself standing in front of a $1 video blackjack machine with a bit of spare time on hand. And I'd developed a new, ingenious method to prolong my playing—keep doubling my bet through a losing streak until I won. So it's all low risk, high reward. Mind you, I still wasn't playing with anything resembling strategy, but at that point, I also still wasn't considering that a flaw.

Somehow, it was working that day. I fed a $20 bill into the machine and started playing. Over the course of an hour or so, I managed to parlay that $20 into $140. That is a 600% return, folks, at which point anyone in their right mind would have said, "I've beaten this machine like a rented mule and thus need to stop now." I, however, seized the opportunity to return the entire $140 in an ensuing span of 15 minutes thanks to an impressive losing streak and my willingness to double up on every losing hand.

The lesson here is that greed kills. You should absolutely realize when you have trounced the odds, cash out your chips, and walk away then and there. By the way, I lost the rest of my money at a $10 table in roughly 20 hands. The only good news is that my prior experiences made me buy a wallet card of basic blackjack strategy before leaving Vegas.

Lesson 3: A Bankroll is a Terrible Thing to Waste

A little knowledge can be a dangerous thing. I now had a reasonable grasp of basic strategy thanks to my wallet card, the Internet, and a good bit of practice on my computer at home. While I was winning more hands, however, I failed to notice the built-in flaw in my betting.

My "strategy" was actually old and tried enough to have a name: the Martingale system. It was designed to make competitively naive chumps like me think that we could beat the house given enough time. The concept is known as negative progressive betting, and you simply increase the bet each time you lose until you win again.

There are some problems with the logic of this, however. First, while the casino will happily let a player lose all the money they want, the table maximum dictates that you will not be able to bet enough to cover an extended losing streak. At a $10 table with the usual limit of $500, you could only sustain a five-hand losing streak while doubling your bets. Second, even assuming that luck is remotely enough on your side to limit your losing streak to five hands, doubling your bet on hand six on that $10 table means you will plunk down $320 after losing $310—cumulatively wagering $630—to win $640. That's right: the longer you lose, the more money you put up just to win a measly $10.

So, armed with strategy and completely unaware of the above pitfalls, I visited the Grand Victoria in Elgin with my gambling buddy one Friday afternoon. I avoided the $25 tables and found a couple of seats at a $10 table. All was going well until the first time I lost three hands in a row. So I'd just bet $10, then $20, then $40...and was counting out the chips to lay down $80 on the next hand. I ignored my friend when he glanced over and whispered, "Are you out of your mind?" And I promptly lost the next hand. So in four hands, I'd managed to lose $150—half of my $300 stake—and didn't have enough to cover doubling the bet for the next hand. At that point, I swallowed what was left of my pride and bet no more than the table minimum the rest of the way.

So, if you're going to play for a long time, you have to know how to limit your losses. There are several strategies for positive progressive betting, for instance. Because you're only raising bets while winning hands, that at least means you're only losing the table minimum bet each hand when you're on a cold streak. Compare losing $40 on four straight hands to losing $150, and you can see the benefit.

Parting Thoughts

I've found it helpful to leave behind the credit, debit, and ATM cards when I go into a casino. If you run out of hard cash, you're done. It's a pretty easy way to avoid turning a small loss into something much worse. And remember, although betting systems may help you manage your losses, they don't affect the odds on any given hand of whether you win or lose. Practice enough to be completely comfortable before you play, and give yourself the best chance to enjoy the game.


"That's Why They Call It Gambling" (J. M. Pressley, 2003), How to Win at Casino Gambling (Roger Gros, 2000)