J. M. Pressley
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That's Why They Call It Gambling

I am not what you would call a compulsive gambler. Sure, I like a good poker game every once in a while (as long as it's with people I know), and I tend to have some fun with casino game packages on my home computer. Where else am I going to put up a $1,000 stake on the spin of a roulette wheel? But in real life, I wouldn't plunk down a cool grand on a single bet—unless, perhaps, Bill Gates walks in and hands me his credit card. Ah, but I do have one slight weakness: blackjack.

Out of all the table games, blackjack has always been a favorite of mine. There is the element of mystery as the dealer flips up the hole card, that pang of hitting on a hard 12 and crossing your fingers that you won't draw a face card, the speculation of betting without any indication what the outcome will be. And it's an easy enough game to understand: get as close as possible to 21 without going over and beat the dealer's hand. It's deceptively simple. Of course, you throw in rules about splits, doubling down, and card counting, and it gets more complicated, but this is a game—and I can't stress this enough—that is fairly easy to play when you're downing gin and tonics on every shoe. Consider a game like craps, and you can appreciate the relative ease of decision making.

The frustrating thing for me, however, with blackjack, is that it has taken so long to get any good at it at all. By good, I mean that it takes me a while to lose my stake. But blackjack is mildly addictive to me (less so than nicotine, although the cost gap between playing blackjack and keeping stocked with cigarettes is narrowing). It has little to do with money gained or lost; a shoe can play relatively quickly, and I consistently think that any losing streak is only a hand or two away from changing. Those qualities, like a low-grade narcotic, have always made blackjack a dangerous proposition for me where actual cash is involved. The other danger in blackjack for the first 35 years of my life was that I played more or less oblivious to anything resembling strategy, either with cards or betting.

Fortunately, I have a number of things in my favor. I grew up in an era where essentially the only real places to gamble were Las Vegas and Atlantic City, and I've never lived in close proximity to either site. Hence, I've not really spent a great deal of time in casinos. Now, of course, living in Chicago, there are any number of choices between casinos, riverboats, and reservations in a 40-mile radius. By this time, however, I have a wife, a mortgage, and a student loan that all combine to keep me from spending too much time or money at the tables; also, I've always understood the adage about not going to the table with any amount that you're not prepared to lose. Having said all that, I have a competitive streak in me that gets a bit stoked when it comes to games of chance. Combine that with my utter lack of strategy, and you have a recipe for being humbled.

The first time I ever sat down at a blackjack table in a casino is a perfect case in point. I was at Harrah's in Indiana with my friend, Ethan. While Ethan veered off for Pai-Gow Poker, I had decided that it was time to try blackjack for real. That was probably my first mistake. My second mistake was choosing a $25 minimum table to start with. That's $25 per hand, folks. Big mistake. My third mistake was making the first two mistakes while having no card strategy whatsoever. Okay, that's not entirely true. I did know enough to stay on a 17 or above, but that was about the extent of my "strategy."

Let me explain how the next three minutes, four hands, and $100 all went: badly. Of course, the first hand I got dealt a hard 12, hit, drew a king, and busted. I plunked down another $25, got dealt a 17, stayed, watched the dealer draw to a 19. I plunked down another $25, got dealt a 20, chuckled to myself, and stayed. I watched the dealer draw two cards to a 21. At this point, I was so ticked that I plunked down yet another $25 in chips and hit on a 15 (I don't even remember what the dealer's up card was). Again, let me point out that I have just bled $100 in less than five minutes on four straight losing hands. The only upside at the time was that it was a hell of a lot easier to walk away from a $25 table under those circumstances, which I did, feeling poorer in more ways than one for the experience.

When I met back up with Ethan a few minutes later, he was kind enough to point out the folly of playing blackjack for the first time on the $25 table. I thanked him for his wisdom and made my way toward the slot machines, as I was in no mood to try my luck at another table. Naturally, that first round of blackjack had pretty much set a tone for the evening, and I blew through $250 worth of cash in little more than an hour. As I told Ethan later, I would have made the money last longer by changing it into singles, shaking hands with everyone I met on the floor that night, and slapping a dollar bill in their hand. Honest.

Needless to say, that put me off of gambling for approximately two years. I contented myself with losing fake money on my computer. It also made me feel better that I could swear at my computer and no one would ask me to leave the pit. Then we went to Vegas.

Neither my wife nor I had ever spent time in Vegas. We got a great deal at Caesar's Palace for a three-day weekend, scored some show tickets, and flew off to Nevada. Now, however, I had a dual strategy for playing longer at blackjack. First, I discovered that the Palace had video blackjack games on the floor, so instead of betting $25 a hand, I could play hands for a mere dollar. Second, I had done some figuring—although, as it turns out, not nearly enough—and come up on my own with an idea of how to keep winning money, and hence, keep playing. A deceptively simple idea for a deceptively simple game. You want to talk about odds; what are the odds that I would lose to infinity? I would simply start with the minimum bet, and double that bet for every loss until I won again. At the end of every streak, I'd be in the black. Again, I'd like to point out that I have a weird denial complex about long losing streaks; every losing streak is just one hand away from breaking.

You can just hear the phrase, "Wile E. Coyote...super genius!" bubbling on my lips as I'm working out this strategy.

What exactly was the net effect? I turned a $20 bill at the video blackjack machine into $140. Did I cash out? Nope. I managed, in much less time than it took to accumulate $140, to lose $140 at this machine. Of course, I convinced myself that my only problems had been greed and a machine programmed to beat the player at critical points. Later in the trip, I spent a little time at a $10 minimum table with a real dealer and everything. However, it was $10 a hand and I only had a $100 stake at the table, so I pretty much kept at about the minimum bet and lost my stake over the course of about 20 hands. At least my sports bets came through that weekend. I'd probably be better off at the sports book than the table games, but I was convinced, in the absence of evidence to the contrary, that my plan was sound. And, as a result of my losses, I picked up a blackjack strategy card at the airport on the way home. Aha, now I was armed with a basic strategy of when to hit, stay, split, and double down based on the dealer's up card. And, as I've already pointed out, I had devised a seemingly foolproof betting strategy to keep in the black.

There is nothing more dangerous than a little knowledge. I know that now. Although in my multitude of computer practice sessions I saw a marked improvement in my winning percentage on a hand-by-hand basis, it's still gambling. I won some fake money, lost some fake money, and generally ignored the fact that my betting was actually one of the oldest, simplest strategies known to gamblers: the Martingale system. It's a negative progression betting system—one in which you increase your bet when losing—and here's where the logic of it breaks down on, say, a $10 table:

Loss Bet Cumulative Dollars Wagered
1 $10 $10
2 $20 $30
3 $40 $70
4 $80 $150
5 $160 $310
6 $320 $630
7 $640 $1,270
8 $1,280 $2,550
9 $2,560 $5,110
10 $5,120 $10,230

At this point, let's assume there is a merciful God who won't allow 11 consecutive losing hands. You bet $10,240 and win on hand 11, and you win $20,480 after wagering a total of $20,470. That's right, you have wagered over $20,000 for the chance to win $10. And here's the additional problems with this system:

You see, it's one thing to lose a grand or more of computer money that you never really had to begin with. It's quite another thing to feel the chips in your hand and commit yourself to the "once more into the breach" philosophy. Especially given that although the house will let you lose ad infinitum, it will not let you bet ad infinitum to try to beat them. High risk, low reward. And I hadn't even figured out that whole critical flaw thing in the strategy yet.

Now, armed with a cocksureness that could only be born of ignorance, I agreed to go on another gambling trip with my good friend, Ethan. Ethan, by this time, had an MBA and had already worked through the financials of the Martingale critical flaw. However, I was counting on finding a video blackjack machine and then a $5 minimum table on which to put theory into action, and I had a $300 stake with which to operate. I was determined, in my own words, to lose money more slowly than my previous trips to the blackjack table.

Mission accomplished.

We hit the Grand Victoria in Elgin in the early afternoon one Friday, and I set out to reap the whirlwind. The first blow to my plan was the utter lack of video blackjack machines in the casino. Okay, no problem; surely I should be able to find my $5 minimum table. Nope. The Grand Victoria tables started at $10 (and went all the way up to $50). And all the $10 tables were packed, of course, because not many people are stupid enough to play at $25 tables. I finally found a table with a couple of open seats, cashed in for some chips, and set about trying to play with strategy for the first time in my life.

All was going fairly well, but the four-hand loss snake bit me about halfway through the third shoe. For the effect this had on my bankroll, I refer you to the table above as well as the comment of Ethan, who was sitting beside me when I put down an $80 bet on the fourth hand: "Are you out of your mind?" I had lost four hands in a row, and in doing so, because of doubling my bet each time, I'd just lost $150 in the span of four hands. Exactly half the money I'd had on me when I walked in. And I'd just lost more money in four hands on a $10 table than I had lost at Harrah's on the notorious $25 table. I managed to quell the nervous tic I felt developing in my right eye, swallowed what pride I had left, and orchestrated the betting equivalent of a fighting retreat. Yep, I went back to pretty much betting the table minimum. Napoleon couldn't have been prouder of his winter march out of Russia than I was of my backpedaling at that point.

The bottom line was that I did manage to lose an entire $300 bankroll, largely on blackjack, but I managed to play at the table for nearly an hour and a half in the process. And though I'd lost money, I'd gained that ever elusive, priceless commodity: knowledge. Specifically, I'd gained the knowledge that my betting was crap.

So, I find myself now experimenting with positive progression systems, which is to say, you're only increasing your bets while you're winning. The theory behind this is that you're only risking your winnings—assuming, that is, that you have winnings to wager. I've lately been putting the 1-3-2-6 system to its paces. The theory of this is that you bet in increments as you win (up to a total of four hands in a row). So you make a first bet of $10. You win and you make the second bet $30. If you win the second bet, you would make a third bet of $20. On the fourth bet, you put in $60. Assuming that fourth win in a row, you have just netted a profit of $120 on a total risk of $20 of your stake.

Results to this point have been mixed, as I have played through six times on the computer on a $200 bankroll and followed the strategy to its logical conclusions. The first couple of times, I doubled my bankroll. The second couple of times, I broke even. The last couple of times, I lost the entire stake, but in both instances, it took over 150 hands each to do so. Is it foolproof? Hell no. I'd have to be a pretty good card counter to stand a better chance at ending up in the black. But it's an improvement, that's for sure. I'm just trying to be a little smarter with my taste for blackjack, even though I realize that any time you walk away from the table with money in your pocket, you've already beaten the odds.

Remember, that's why they call it gambling. If it was a surer bet, they'd call it investing.

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