Bracketology with a five year-old

That I can win anything in the world of sports prediction is a testament to its ridiculousness.

I am not a sports bettor. I can’t stomach it. Frequent readers will raise their eyebrows, because I’m known to make a wager here and there on the outcome of such things as the turn of a card, the flip of a coin, the toss of a lime, the number of pins knocked down in ten frames of bowling, or whether Ally Sheedy appeared in Season 5 of Weeds (she didn’t; it was Jennifer Jason Leigh, and I won).

Your cognitive dissonance aside, there is some reasoning behind this. I like to bet on things in which I have some skill (poker, lime tossing) or on random things in which skill and knowledge play no role (bowling). Sports betting requires a combination of exceptional hubris and intelligence, neither of which I can claim.

Thus, betting on sports makes me want to throw up on myself. Oh, sure, I do it from time to time for nominal amounts (the betting, and to a lesser degree, the puking), but I’m rarely happy about it.

“The secret to running a sports book,” a bookie told me recently, “is that 90% of the public can’t pick a winner.”

Though that bookie got a great argument about his methods from somebody far smarter than me, I feel it safe to say that I am part of that 90%. Your surest way to win a sports wager is to find out what I bet and fade me at every opportunity. It’s like the easiest way to make sure you’re living a moral and socially just life: listen to what Glenn Beck preaches, and then do the opposite.

Last year, I managed to win the first prize $420 (that’s fictional, hypothetical, legal non-money, of course) in Pauly‘s annual Pauly’s Pub March Madness pool. Unlike a lot of the big pools I have a chance to enter–and don’t–this one has a small entry fee, but comprises some of the best sports and betting minds I know. My victory was proof that not only anybody can win, but somebody as tragically handicapped in the world of sports betting can win a NCAA March Madness pool.

And so we’ve come to 2010, the year my five-year-old son will get his first taste of the value of picking at near-random for the chance to win untold fortunes (or, in this case, up to 420 completely fake, hypothetical dollars).

The way I see it, with a few simple rules, I can teach my son to pick as well as I can in the NCAA March Madness tournament. I am fronting him the buy-in. Whatever he wins, he will be allowed to spend on anything he wants (this rule passed the steering committee after it was determined that there is no way the kid will be able to find a cheetah for $420).

This afternoon, I will sit the boy down and let him fill out his bracket with the following rules:

In Round 1 he must pick the higher seed in the 1 vs 16, 2 vs 15, and 3 vs 11 games. Out of the four 4 vs 13 games, he must pick one upset. In all the other games, he is free to pick whatever team he wants. In Round 2, the 1 seed must advance. All other games in Round 2 and going forward are free pick.

Do I expect him to win? No. Will I have a great time making fun of everybody who finishes below him? Absolutely.

Oh, and if for some reason the kid picks the Kansas Jayhawks to go all the way, I’m getting a paternity test tomorrow.