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.
Again, your overall strategy should be to look for situations where the national bracket values a team much higher than the objective statistics. (I should stipulate that all of this advice assumes standard NCAA pool rules, where the points for a correct guess double each round, from one point in the first to 32 for the final game.) For example, at the moment only 1.8 percent of all the participants in ESPN's Tournament Challenge have picked Texas to win the tournament—the right-most column on this table. Pomeroy's log5 analysis of the tournament, by contrast, gives the Longhorns a 5.8 percent chance of winning it all. This makes Texas a fantastic bargain, even if their odds of winning the title are still remote—while cold-blooded, numerical analysis gives Texas a 1-in-17 shot at the title, only one in 56 people have picked them to win. As such, the Longhorns are the most- undervalued asset in the 2011 NCAA Tournament. (The reviled Duke Blue Devils were the best bargain in both 2009 and 2010. If you followed the advice of this column last year and picked Duke, you probably won your pool. I did.)
On the other hand, Kansas—the second most-popular pick on ESPN, trailing only Ohio State—is definitely not a bargain. While 21.7 percent of the ESPN crowd has Kansas taking the title, the team's Pomeroy odds stand at 12.4 percent. Although anyone who watched the Big 12 title game on Saturday would believe that Kansas is a better team than Texas, I believe the Jayhawks are a much worse bet. Which would you prefer, the team that more than one-fifth of your pool will also pick (Kansas) or one that nearly no one else will favor (Texas)? I would take the second—at least, if I wanted a chance to win the prize money instead of just placing respectably. (This assumes your pool resembles the country at large, of course; a pool among Texas undergraduates probably would not offer the same generous odds.)
Biostatistician Bradley Carlin, who co-authored a 2005 paper (PDF) on contrarian strategies in NCAA brackets, suggests a "champion-only" technique. While most people spend a lot of time puzzling over potential first-round upsets, the mathematical reality is that it's difficult to win a pool without securing those boffo championship game points. The payoff for risk-taking also increases in later rounds. Consider the first round game between 12-seed Utah State and five-seed Kansas State. Only one in four ESPN players predict that Utah State will pull off a fabled 5-12 upset, while Pomeroy gives the Aggies a 60.1 percent chance of making the second round (though he does express some reservations about the strength of this figure in his introduction). On paper, that differential looks like a great bargain. But consider that this upset will reward the lucky Utah State fan with a mere one extra point in a standard office pool. If Kansas State wins, you're suddenly missing an important player in the bracket.
Whom should you pick as your champion? You want to look for teams with a respectable chance of winning that don't come in with high expectations. As the size of the pool balloons, so must your audacity. You may skate to victory with traditional choices in a group of 12 people, but in a pool of 100, you'll have to get fancy and prepare to lose miserably if the cards don't fall your way. Along with Texas, other good bargains in this year's field are Purdue (picked to win the title by 0.9 percent of ESPN.com competitors; a 5.1 percent title chance according to Ken Pomeroy) and San Diego State (1.7 percent on ESPN.com; 5.0 percent Pomeroy). And along with Kansas, one of the worst values in the field is the University of Connecticut—6.2 percent of the folks on ESPN.com like Kemba Walker and the Huskies to win it all, while Pomeroy gives them a mere 1 percent chance of hoisting the trophy. (This year, college hoops fans have finally valued Duke correctly: The Blue Devils are the choice of 15 percent of ESPN.com users and have a 15.3 percent chance to win according to Pomeroy.)
Of course, the trouble with picking an off-the-radar champ is that the benefits of such a strategy materialize only in the long term. Another author of that 2005 paper on bracket strategies, Jarad Niemi, told me that he has won back three to four times his investment in entry fees over the years, but a great deal of that came from a good year in 2008. (Considering how good they are at calculating risk, it's no surprise that guys like Niemi and Carlin excel in pools that award bonus points for upsets. Carlin said he won one such pool three out of five years.) A strategy that wins you a lot of money a small amount of the time may work well in sports with long seasons, but it can be tough to keep the faith when you finish in the cellar for six straight Marches. But look at it this way: Did you ever win with your old strategy?