Entering contests is not about fun. It is not about making runs, great games, or cheering for your teams. It is about beating the man. Taking his money. Extracting his wealth and making it your own.

To that end, here is some advice to beat all the suckers that do not turn brackets into math exercises.

There is one “rule of interest” that dominates your bracket tourney selection process in the first round. You earn one point PLUS the seed differential if you select an underdog that wins. When the brackets come out, the sportsbooks will immediately put up spreads and moneyline prices for each game. As any machine controlled by pure logic would do, you want to make selections that maximize your expected scoring in the contest.

In this first round you should have only two considerations: Which first round selection will give you the most “expected points”, and will that selection hurt you in the second round. Consider a matchup between the #8 and #9 teams.

If they are truly equal and the spread is “Pick’em,” the expected points (EP) for that matchup are easy to determine. If you pick the #8 seed, you should win half the time earning 1 point, for an EP of 0.5. If you pick the #9 seed, you still win half the time, but claim two points (1 + the seed differential)… or an EP of 1.0. You correctly select the #9 seed, and smile as you just gained a tiny bit of equity over all the other players who foolishly picked the #8 seed.

If a game is not lined at “Pick’em” you have to estimate the odds of each team winning in the first round. You can do this very accurately, even if you know nothing about basketball.

Simply look at the moneyline prices, and convert it into a win percentage. For example, if a matchup between a #6 and #11 team had a moneyline of -185 on the favorite and +165 on the underdog, you would take the mid-point of the absolutes – 175 – and divide by that midpoint + 100. In this example, the win percentage for the favorite would be:

175 / (175 + 100) = roughly 64% for the #6 seed, and 36% for the #11 seed.

What are your expected points for each selection? For the favorite - #6 – it is simply the win percentage – 0.64. For the underdog it is 0.36 * 6 (1 + the seed differential of 5), or about 2.1.

With these rules, it will make sense to pick almost every underdog in the first round. But there is one catch – if you pick the underdog, you can not pick their opponent in the second round or later. This will cost you up to two points if you would have picked that second round matchup winner, and even more for later rounds. While I would normally bet every first round dog, I would normally pass if that means eliminating one of the regional Top 4 seeds in the first round. Anything else goes. In a standard contest without an odd first round rule, you can still use EP math to make selections - simply pick each team that is a favorite on the spread/moneyline.

In Part II, I will fill out my entire bracket, and explain reasons for all the other selections.

*© Copyright 2009. Reprinted with permission of the author. *