A version of this article originally ran in 2009. In 2010, our advice to bet on Duke paid off when the Blue Devils won the title. Our suggestions to pick Texas in 2011 and Ohio State in 2012 did not go quite as well. (The Buckeyes, at least, made the Final Four.) Our picks from 2013–2016—Florida, Arizona, Arizona again, and Virginia—all made the Elite Eight. Our 2017 pick, Gonzaga, made the title game, but last year’s pick, Cincinnati, lost in the second round. Choose wisely!
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 crowdsourced 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 past 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 TeamRankings, 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.
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 round to 32 for the final game.) For example, as of 2:45 p.m. on Monday, only 6.5 percent of all the participants in ESPN’s Tournament Challenge have picked Virginia to win the tournament—the rightmost column on this table. Pomeroy’s log5 analysis of the tournament, by contrast, considers the Cavaliers the favorite, giving them a 20.5 percent chance of winning it all. This disparity is likely explained (at least partly) by last season’s tournament. Virginia was the most popular pick to win the title, only to become the first No. 1 seed to lose in the first round. A year later, after the Cavaliers went 29–3 and received another No. 1 seed, contestants are still shying away. This makes Virginia a decent bargain—while coldblooded, numerical analysis gives the Cavaliers a roughly 1-in-5 shot at the title, only 1 in 15 people have picked them to win. As such, Virginia is the most undervalued asset in the 2019 NCAA Tournament.
On the other hand, Duke—the most popular pick on ESPN.com—is not a bargain at all. While 43 percent of ESPN users like the Blue Devils, Pomeroy’s log5 analysis gives them a 13.9 percent shot.
Although fans who’ve watched Duke twice beat Virginia head-to-head this year might believe Duke is the better team, the Blue Devils are a worse bet. Which would you prefer, the team that a bunch of other people in your pool will also pick (Duke) or one that very few will favor (Virginia)? I would take Virginia—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 Virginia undergraduates probably would not offer the same generous odds.)
Biostatistician Bradley Carlin, who co-authored a 2005 paper 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. 6 seed Villanova and No. 11 seed St. Mary’s. Just 22.4 percent of ESPN players predict that St. Mary’s will pull off the upset while Pomeroy gives the school a 47.7 percent chance of winning the game. On paper, that differential looks like a good bargain. But consider that this upset will reward the lucky Gaels backer with a mere one extra point in a standard office pool. If Villanova wins, St. Mary’s supporters are 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.)
Other than Virginia, there’s another decent bargain in this year’s field. If you don’t like the Cavaliers, go with Michigan State. Though the No. 2 seed Spartans have been picked to win the title by just 4.3 percent of ESPN.com competitors, Michigan State has a 10.9 percent title chance according to Pomeroy—the fourth-best odds in the field. Michigan is also slightly underrated by the crowd, with ESPN.com users giving the Wolverines a 3.1 percent shot to win while Pomeroy has them at 5.8 percent. If you want to go for a No. 1 seed, Gonzaga isn’t a bad bet either: Pomeroy says the Bulldogs have the second-best odds of winning the tournament, at 15.4 percent, but only 7.5 percent of brackets on ESPN.com have them winning it all.
Who’s another bad pick? You won’t get great value from Duke’s rival North Carolina either. While 14.2 percent of ESPN users like the Tar Heels, Pomeroy’s log5 analysis gives them an 8.7 percent shot.
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 his investment in entry fees three to four times 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?
