Winning a pool is not a matter of luck; it’s a matter of maximizing utility and playing the odds. Image courtesy of Flickr user MajerLeagues and licensed under CC by SA 2.0

The greatest college sports month of the year is finally here, and whether your school is in the Big Dance, the NIT, or (like mine) Division III, you can still have a great time filling out a bracket and trying your luck in a friendly pool. 

Oh, I’m sorry. Did I just type “luck,” and then purposely not go back and correct it for dramatic effect? Yes I did. Luck has little to do with winning an NCAA pool. It can be tempting to pick most of the top-seeded teams all the way through to the later rounds, and this strategy will almost certainly keep you out of the cellar, but it’s not likely to win you any money. Picking individual matchups is a complete crapshoot.  Building a bracket that will win your pool is decidedly not. Here are some tips and tools to help you finish on top. 


Know the Rules

Pool ruless score brackets a variety of ways, and it’s important to consider this when filling in your winners. Many will reward you with bonus points for correctly choosing upsets, meaning that the more low seeds you choose, the higher your potential total score. I’m not saying you should pick UTSA to beat Ohio State in the first round, but you’ll definitely be better served by taking some risks, especially in the later rounds when upset picks often become exponentially more valuable. This is the strategy I used to win a pool in 2008, riding the Davidson Wildcats to a cool $200.

Most pools will do something like add the seed number to an arbitrary point value for each round, meaning that picking the #1 Duke Blue Devils would net you 1 x, while correctly picking Hampton in the game would earn you 16 x. I have seen a few competitions though where bonus points were only added to x if the winning team was seeded lower. If this is the case, you may want to sacrifice the overall integrity of your bracket in order to hit the jackpot on a couple of upsets. Picking every 9, 10, 11, and 12 seed in the first round would almost certainly get you several upset bonuses, while still keeping the strong 1-4 seeds available for the lucrative later rounds.


Start with your Sweet 16

While it isn’t unheard of, usually by the second weekend of the tournament most of the Cinderella hopefuls have been knocked out. Start your bracket by choosing your most likely Sweet 16, and go from there. The later rounds will usually get you more points, so it’s the one places where it often pays to play it safe. Once you’ve picked your champion, go back and fill in your first two rounds, placing an emphasis on upsets. In these early rounds, getting every individual game right is much less important than picking the correct upsets to score bonus points, as each correct pick usually has a lower base value. As long as you’ve pared it down to the safer choices by the second weekend, it’s okay to miss a lot of early games in order to correctly predict a few upsets.


Play the Bracket Across From You

Wired posted a great resource today that compares the national average of bracket choices on ESPN to the usually-prescient Ken Pomeroy and Jeff Sagarin team rankings. They created a spreadsheet that shows which teams are overvalued and undervalued in each round, allowing you to pick against the crowd and differentiate yourself from the pack. In these pools, playing a similar bracket to everyone else is a recipe for mediocrity. If you want to take some of your friends’ cash, you need to keenly distance your entry from those of your opponents. Though the Wired article gives a much more thorough explanation of the concept, just know that by choosing teams that are undervalued by your opponents, you give yourself the opportunity to score more points than them. When you give yourself a higher potential score than your opponents, you have more breathing room to miss a few games, and still finish out on top. 

Have you filled out your brackets yet? Link them in the comments!