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 what the NCAA calls the “second round” to 32 for the final game.) For example, at the moment only 7.2 percent of all the participants in ESPN's Tournament Challenge have picked Arizona to win the tournament—the right-most column on this table. Pomeroy's log5 analysis of the tournament, by contrast, gives the Wildcats a 15.9 percent chance of winning it all, making them the overall favorite, ahead of Florida and Louisville. This makes Arizona a fantastic bargain—while cold-blooded, numerical analysis gives them a roughly 1-in-6 shot at the title, only 1 in 14 people have picked them to win. As such, Arizona is the most undervalued asset in the 2014 NCAA Tournament.
On the other hand, Florida and Michigan State—the top two picks on ESPN.com—are not a bargain at all. In fact, the Gators and the Spartans are both overvalued by the crowd. While 27.8 percent of ESPN users like Florida, Pomeroy’s log5 analysis gives them a 12.9 percent shot; Michigan State is the pick of 12.3 percent of ESPN’s bracketologists and has just a 2.4 percent chance of winning it all by Pomeroy’s metrics.
Although fans who’ve watched these three teams closely over the last few weeks might believe that Florida and Michigan State are better than Arizona, the former two are a much worse bet. Which would you prefer, the team that a bunch of other people in your pool will also pick (Florida and Michigan State) or one that very few will favor (Arizona)? I would take the Wildcats—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 Arizona 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 No. 14 seed North Carolina Central and No. 3 seed Iowa State. Just less than 5 percent of ESPN players predict that North Carolina Central will pull off the big upset, while Pomeroy gives the school a 26.8 percent chance of knocking off Iowa State. On paper, that differential looks like a great bargain. But consider that this upset will reward the lucky North Carolina Central backer with a mere one extra point in a standard office pool. If Iowa 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. (A miserable loss is a good way to describe our pick of the Texas Longhorns in 2011—and our suggestion to avoid Connecticut. Don’t say we didn’t warn you.)
Other than Arizona, there’s one more outstanding bargain in this year's field. If you don’t like the Wildcats, go with the Virginia. Though the No. 1 seed Cavaliers have been picked to win the title by just 4.1 percent of ESPN.com competitors, they have an 11.5 percent title chance according to Ken Pomeroy. Louisville is also slightly underrated by the crowd, with ESPN.com users giving them an 8.5 percent shot to win, while Pomeroy has the Cardinals at 12.3 percent. If you’re looking to back a real long shot, take a look at Villanova (1.1 percent on ESPN.com; 5 percent Pomeroy) and Creighton (1.3 percent on ESPN.com; 3.6 percent Pomeroy). Who are the worst bets in the field? Other than Florida and Michigan State, you’ll get crummy value by backing a pair of bluebloods: Kansas (5.7 percent ESPN.com; 3.5 percent Pomeroy) and Duke (6.1 percent ESPN.com; 3.2 percent 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?