This piece originally ran in 2009. It has been updated for the 2010 NCAA Tournament.
For anyone who, like me, merely hopes to survive March Madness with minimal embarrassment, the introduction of wisdom-of-the-crowd statistics to online bracket contests has been pure salvation. Even though I didn't follow college basketball this winter, I can fake a little competence by basing my picks on what a majority of all entrants think will happen. By copying the "national bracket," as ESPN calls it, I'll lose my $5 with dignity. That's the magic of crowd-sourced bracketology: So long as your office pool is big enough to resemble a cross section of America, you're unlikely to finish in last place.
Of course, you're also very unlikely to win if you copy everybody else's picks. Even if you get the last few games right for the big points, a lot of other people will, too. At least one of them will probably be luckier than you. Still, collective wisdom can be eerily powerful in the right circumstances. The national bracket typically performs well, as various commentators have noted, though it will probably win the money in only a very small pool populated by inexpert players. So is there a way to use these collective picks to your advantage while still having a prayer of taking home the pot?
As it turns out, the wisdom-of-crowds information is extremely useful. The statisticians and expert bracketologists I talked to all urged one central point: Don't think about guessing the most games correctly. Instead, think about finding "bargains" in the bracket where collective wisdom runs askance of more objective measurements. Exploiting games where your fellow bracketologists are likely to guess wrong—even if the odds of that happening are still against you—will give you the best shot at jetting ahead of the pack. An NCAA bracket, then, is more like a long-shot stock than a game; the odds of winning may be low, but the big pot makes the gamble worth it—if you know how to maximize your investment.
The "contrarian" strategy I'm suggesting here isn't new; correctly choosing upsets has always given pool jockeys a major boost. What's changed in the last few years is our ability to value the risk and rewards of a given bet and to decide whether it's worth it. This bracket-picking strategy isn't so different from the way Wall Street became obsessed with modeling risk, as Wired has chronicled. The key is having access to two data sets: the wisdom-of-the-crowds data from the national bracket and a table of more objective stats. By comparing the two, you'll be able to assess whether you're getting bang for your buck when you throw your lot in with an underdog team.
Before you start filling out your bracket, then, you need to choose some measure of team strength that's free of biases and groupthink. Here, the bountiful Internet does not disappoint. Dabblers can choose from many different statistical measures—adjusted scoring margin, the Ken Pomeroy ratings, Jeff Sagarin's computer ratings—that rank teams based on factors like strength of schedule and margin of victory. Other services, like BracketBrains, charge a fee for rigorous analysis, factoring in the results of real games between similar pairs of teams, the distance from each team's home campus, and so forth.
Second, you have to steel yourself for the possibility that your pursuit of first place will leave you in last place. While it may get you ridiculed by your friends, it's important to remember that (at least monetarily) the consequences of coming in dead last are no more severe than coming in a few spots shy of the gold. Act as if you're a hedge-fund manager in the good old days: Risk is your friend, and the consequences of making a bad bet are small. And unlike with a multibillion-dollar hedge fund, you're not playing against opponents with equal fidelity to statistics and information. Your office pool is full of people making decisions based on snippets of games they happened to catch and whatever allegiances or vendettas they're bringing to the table. This is your chance to take advantage.