So, I'll admit it, I have a gambling problem.

Well, it's probably not quite what you'd think but it is a problem nonetheless. I'm not (yet) a compulsive gambler since I don't spend an inordinate amount of time or money on the pastime. In fact over the almost four years since I've been living close to a casino I've only been there three times. The unsettling fact about my recent gambling forays is that I just can't seem to win. Now some quite rational folks might interrupt me here to offer a reminder that this is, in fact, the point. (At least from the perspective of the casino, that is!) Well, for better or worse I'll have none of that. I'll add, as a brief side note, that my most recent gambling session resulted in a loss of a mere $50. Good news, right? Considering the last time I went I somehow managed to drop $250 at the tables, there's really no other way to look at this more recent trip than as a major victory! Okay, now to return to reality.

Once you go Blackjack you never go back

To me gambling is almost always either blackjack or poker. I'll play poker against human opponents, but when I'm playing against the house I prefer blackjack. Now, this game has a reputation of being the only casino game that can actually be beaten. Fortunately for the casino the vast majority of blackjack players seem to interpret this rep as meaning blackjack 'can be beaten by any idiot with a lot of cash who's willing to bet big.' Now you might want to stop me here to ask if these players actually call themselves idiots in their own thoughts like that. Of course they don't but really, a few thoughts in the hands of such people can be very dangerous indeed. So I think we're all better off if I just do the thinking for them.

Back to my point: what this reputation really means is that under certain player friendly rules a player who has the ability to count cards, a proper sized bankroll, mastery of the game's basic strategy, and the discipline to walk away from the table when ahead is theoretically able to beat the game long term. As you may be able to guess, the percentage of blackjack players that fall into this second category is a fraction of a percent, and they certainly win much less money than the first category of players generously donates to the casino.

It pays to be Progressive

Now, as a blackjack player I fall somewhere between these two extremes. I subscribe to a hypothesis presented by Walter Thomason in his book Twenty-first Century Blackjack. Thomason argues that card counting isn't necessary to win consistently at blackjack. He champions a system based on positive progressive betting paired with proper execution of game fundamentals. Positive Progressive betting is simply raising your bet after every winning hand along a predetermined progression. For example, I may follow a 10, 15, 20, 25, 30 betting progression. My first bet would be $10, I would increase it to $15 following a win, and continue to move along the scale until I topped out at $30 or I lost a hand. After any losing hand I would return to my initial $10 bet. Now most mathematicians who have studied the game of blackjack have discarded (no pun intended, really!) this system without much consideration because since each hand is completely independent of the previous one there is no reason for you to believe that the hand following a winner would have any greater chance of being a winner than if it had followed a losing hand. Despite this, Thomason demonstrates such a system's effectiveness through thousands of hands of simulated play.

Streaking for Fun & Profit

Thomason's best explanation for why this system seems to work is that blackjack is a game of streaks. Many times during a playing session a player will experience several (or more) consecutive wins or losses. During such streaks, the positive progressive player will tend to have much more money on the table during winning streaks and much less money on the table during losing streaks. Unfortunately for me during my last trip to the casino, I had more losing streaks than winning streaks. Using this system in such a case can still be beneficial since it minimizes the amount of money lost during such rough sessions. Of course, it's little consolation that I could have lost a lot more!

Perhaps next time I'll be a little more fortunate and end up with some of the casino's money instead of it ending up with mine. Of course, at this point my wife is simply convinced that I'm just plain unlucky and should quit now while I'm only a little in the hole. My philosophy is this: I've been lucky so far in life in lots of ways. Somehow I ended up with a great wife, two healthy kids, and a job I don't hate. Also, I'm still alive. Even more amazing, the Red Sox finally won the world series in 2004. If that isn't being fortunate I don't know what is. From where I'm sitting it feels like only a matter of time until some of that good mojo rubs off on my gambling sessions and sends me home a winner. Finally.