March Madness Bracket Strategy: Contrarian Strategies to Help You Win Your Bracket

March Madness Bracket Strategy: Contrarian Strategies to Help You Win Your Bracket
March Madness Bracket Strategy: Contrarian Strategies to Help You Win Your Bracket

Everyone wants to win their March Madness bracket. But it’s important to remember that college basketball will look different in 2026. It makes sense to pick high-probability events in your bracket.

There is no shortage of analytical resources, such as the omnipresent Ken Pomeroy. On my site, The Power Rank, the highest ranked team has won 70.9% of tournament games in the last 23 tournaments.

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Even with all the resources available now, it is essential that you employ an appropriate strategy when filling out your group depending on the size of your group. Sometimes going against the grain is the way to go. Let me explain to you.

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Use chalk for smaller pools

To explain the two different strategies you could use, let’s use the 2019 NCAA Tournament as an example.

Duke dominated the college basketball landscape in 2019. Mike Krzyzewski’s team featured Zion Williamson and RJ Barrett, two players who would be selected among the first three picks in the upcoming NBA draft.

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Duke’s results before the tournament also earned them the top spot in my college basketball team rankings on The Power Rank. With the simple approach of picking the highest-ranked team in each game, you’ll get Duke as your 2019 champion.

I called this the favorites strategy in my book How to Win Your NCAA Tournament Bracket and it will give you the most expected points in your bracket. By my numbers, Duke had a 34% chance of winning the tournament, the highest of any team. For small groups, this is the optimal strategy.

However, you can increase your chances of winning a medium-sized fund with another strategy.

How to be contrary in larger groups

To see this, let’s say you’re in a group of 50 people. According to Yahoo Sports’ Bracket Mayhem public pick distribution tab, which has data on millions of brackets, 30% of brackets chose Duke as the champion. This means that around 15 people choose Duke in their group.

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If Duke wins, then you and 15 other people will get those 32 points for choosing the champion, which is the most important choice in your group. With so many people in the running, chances are one of those people will make some outrageous decisions in earlier rounds and beat you.

Instead, you’ll want to make the opposite decision and choose against the favored Duke. You find a team with a high probability of winning but is not chosen by others in your group.

In 2019, the opposite option was Virginia. Tony Bennett’s team featured future pros De’Andre Hunter and Ty Jerome. However, they were overshadowed by ACC rival Duke and lost both games in the regular season.

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According to the data, only 8% of groups chose Virginia as champion. One factor was that Virginia had lost to No. 16 UMBC in Round 1 of the 2018 NCAA tournament, the first No. 1 seed to lose to a No. 16 seed in men’s tournament history.

My college basketball numbers gave Virginia a 22% chance of winning the NCAA tournament. Note the large difference between Virginia’s probability of winning and the 8% of the groups chosen by the people in the groups.

Think about the 50-person pool. Only four people will choose Virginia as champion. If Virginia wins, then you and only four other people will have the right champion. Your solid chalk picks in the previous rounds should be good enough to ensure victory.

The opposite strategy worked in 2019, when Virginia won the NCAA tournament.

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Two finer points on the contrarian strategy

Let’s look at two key elements about favorite versus contrarian strategy.

First, the contrarian strategy works best with a large gap between a team’s probability of winning and the fraction of groups that choose it as champion. In 2019, the gap for Virginia was about 14%. From the simulation results, I estimate that the contrarian strategy begins to beat the favorite strategy for groups with 20 or more people.

(Bracket Mayhem 101: How to Use Expert Picks to Complete Your Bracket)

With a smaller gap, your probability of winning with favored and opposing strategies can be comparable for group sizes up to 100. Regardless of the gap, I recommend submitting multiple groups that use both strategies.

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Secondly, you can also go beyond the data on which team they choose as champion. Common sense works too.

As an example, in 2026, let’s say you’re in a group based in Ann Arbor. It’s safe to assume that a large fraction of people will pick Michigan as the champion because of the way the Wolverines have played this season. The same thinking works for groups full of alumni from title contenders like Duke and Arizona.

Pool strategy in 2026

The 2026 NCAA Tournament will be a particularly interesting year to apply favorites versus opponents strategies.

Looking at the BetMGM futures market, Michigan and Duke are the favorites to win this year’s tournament. I expect these teams to have the highest pick percentage as champions, something you can check out on Yahoo as you fill out your bracket.

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The best teams in college basketball have been historically good this season. In my team rankings, which take margin of victory and adjust for strength of schedule, Arizona, Michigan and Duke score 23 points better than the average Division I team. This is close to the rating with which Florida entered the tournament last season, but much higher than the 20 points of the top teams in previous years.

(Best bets on all NCAA Tournament games)

Additionally, Duke and Michigan are also similar in that they will both miss key point guards in the tournament. Caleb Foster remained in the Duke program for three seasons and finally earned a starting role this season. He underwent surgery for a broken foot and will almost certainly miss the entire tournament.

LJ Cason didn’t start for Michigan, but he could easily make a case as the top point guard ahead of Elliott Cadeau. Cason will be out for the remainder of the season after a torn ACL suffered against Illinois.

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A team with opposing value could be Arizona, even as a number one seed. The Wildcats did not enter the season with championship expectations, as they were ranked 13th in the preseason AP Poll. However, the Wildcats have excelled on both ends of the floor and are actually ahead of Michigan and Duke in my college basketball team rankings.

Ed Feng runs The power rangean analysis site dedicated to sports betting.

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