One day after I had been hanging out at Speeds pool hall for about a year, Stacy brought a cheap chess board in. The management had frowned on him dealing blackjack with his buddies, even though it was just for fun and to kill time while drinking. In Texas, public gambling was (and for the most part, still is) strictly taboo…even though everyone there knew a half-dozen guys that would take sports book, and you could gamble on just about any activity in the room from pool to darts to pinball. Just don’t LOOK like you’re gambling. Anyway, Stacy thought chess might be interesting, something out of the ordinary to fill the spaces when nothing else was going on.

So Stacy and I were drinking Shiner Bock, telling lies, and moving a chess piece from time to time. I hadn’t played much in a couple of years, but like most dorks in high school, spent some time in semi-focused study of the game and was still a better-than-average player as an adult. Tom the bartender looked over and saw the board and hollered, “Hey, if I get a break, I’ll play the winner!” I kinda scratched my head at that one…Tom wasn’t half as smart as he thought he was, and even he knew either one of us would slap him around the board. Sure enough, Tom got a break, Stacy got distracted with something else, and I set up the board for our game. I never mentioned a wager, and knew I didn’t have to. I don’t even think both ass cheeks hit the chair before Tom said, “Put $10 on it?” About 20 minutes later, a couple of knight forks, a queen gambit when I was already up, I had paid for my next couple of drinks.

Just as we were finishing up, some guy we didn’t know came by and asked if he could play too. At this point, Prof. James Acquaintance and I looked at each other and figured we might be on to something. Chess was, and still is, a perfect game to hustle…you can distract guys, talk shit to influence play, give people spots that look good but really don’t mean much, sucker them in with bad plays, etc. Over the next month or so, James, Stacy and I tried to line up games for each other. The end goal was to set me up for the biggest games, since I was pretty much the most experienced player, but it couldn’t look like I was sitting there waiting for the next lamb to slaughter. So we all circulated, we all talked, and we all played whomever we could find at $20 or $50 a game, buying each other drinks with the winnings and putting a couple of bucks in our pockets here and there.

We thought we had a fun little deal worked out…but it dried up before it really got rolling, much to our surprise. It seemed too good to be true, which of course means it was…but it took forever before anyone could hypothesize why. We never really came up with a great answer, other than that chess is just too much thinking to keep a casual person interested. In most great prop bets, the sucker takes the bet, loses simply and easily, and walks away. That’s their role, and for the most part, they’re OK with that. People who make bets rarely mind losing them…if they didn’t, there wouldn’t be a Las Vegas, Atlantic City, Macau, Monaco, etc., etc., etc. - players would go until they lost (usually just one trip) and never come back. But casinos are packed with regulars, almost all of whom lose with overwhelming regularity. People are OK with getting beat…they just don’t want to have to WORK at it.