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 4 percent of all the participants in ESPN's Tournament Challenge have picked Ohio State to win the tournament—the right-most column on this table. Pomeroy's log5 analysis of the tournament, by contrast, gives the Buckeyes an 18.7 percent chance of winning it all, making them the second favorite in the field behind Kentucky. This makes Ohio State a fantastic bargain—while cold-blooded, numerical analysis gives Ohio State a roughly 1-in-5 shot at the title, only one in 25 people have picked them to win. As such, the Buckeyes are the most undervalued asset in the 2012 NCAA Tournament.
On the other hand, John Calipari’s Kentucky Wildcats—the most popular pick by ESPN users—are definitely not a bargain. While 32.2 percent of the ESPN crowd has Kentucky taking the title, the team's Pomeroy odds stand at 19.5 percent. Although most people who watched both teams play this year would believe that Kentucky is a better team than Ohio State, I believe the Wildcats are a much worse bet. Which would you prefer, the team that one-third of your pool will also pick (Kentucky) or one that nearly no one else will favor (Ohio State)? 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 Ohio State 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 14-seed St. Bonaventure and three-seed Florida State. Less than 4 percent of ESPN players predict that the Bonnies will pull off the big upset, while Pomeroy gives St. Bonaventure a 33.8 percent chance of knocking off the Seminoles. On paper, that differential looks like a great bargain. But consider that this upset will reward the lucky St. Bonaventure backer with a mere one extra point in a standard office pool. If Florida 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 last year—and our suggestion to avoid Connecticut. Don’t say we didn’t warn you.)
Along with Ohio State, who are the other potential bargains in this year's field? The next best bet is Kansas, which has been picked to win the title by 5.9 percent of ESPN.com competitors but has an 8.6 percent title chance according to Ken Pomeroy. And if you’re looking to back a real long shot, take a look at Wisconsin (0.3 percent on ESPN.com; 4.0 percent Pomeroy) and Wichita State (0.2 percent on ESPN.com; 2.5 percent Pomeroy). Who are the worst bets in the field? Along with Kentucky, you’ll get the crummiest value by backing the second and third favorite picks of ESPN.com users: North Carolina (15 percent on ESPN.com; 9.3 percent Pomeroy) and Syracuse (11.1 percent ESPN.com; 4.3 percent Pomeroy). Duke is overrated as well: The Blue Devils are the choice of 4 percent of ESPN.com users and have a 1.2 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?