March Madness bracket strategy: Contrarian strategies to help you win your bracket pool

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

There is no shortage of analytics resources out there, like the ubiquitous Ken Pomeroy. At my site, The Power Rank, the higher ranked team in my pre-tournament college basketball team rankings has won 70.9% of tournament games in the last 23 tournaments.

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Even with all of the resources now available, it’s critical that you employ proper strategy when filling out your bracket depending on the size of your pool. Sometimes going contrarian is the way to go. Let me explain.

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Using chalk for smaller pools

To explain the two different strategies you might 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 both get drafted in the top three picks of the next NBA draft.

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

I called this the favorites strategy in my book How To Win Your NCAA Tournament Pool, and it will get you the most expected points in your pool. By my numbers, Duke had a 34% chance to win the tournament, the largest of any teams. For small pools, this is the optimal strategy.

However, you can increase your chance to win a medium-sized pool with another strategy.

How to be contrarian in larger pools

To see this, let’s assume that you’re in a 50-person pool. Based on the public pick distribution tab from Yahoo Sports’ Bracket Mayhem, which has data on millions of brackets, 30% of brackets picked Duke as champion. This means about 15 people pick Duke in your…

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Author : Ed Feng

Publish date : 2026-03-17 18:38:00

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