Trying to win your bracket pool depends on a lot of factors.  One of the biggest factors you should consider is the prize pool.  It doesn’t take a rocket scientist to figure out that the fewer people that are in your pool, the better chances you have to win your pool.  But if you are in a large pool, (let’s say 100 or more people) then you need to adjust your strategy.

Similar to playing in a large contest in daily fantasy sports, you are going to need a unique entry in order to win.  Kansas beating Michigan State in the title game is what everyone else has, so if that happens, you better hope you nail all of your first and second round upsets to win your pool.  The better strategy is to try to find a bracket that other people in your pool won’t have that still has a legitimate chance to happen.

The key to this strategy is balance.  Picking all the 16-seeds to go to the Final Four will certainly be unique, but the implied probability of that actually happening is essentially zero.  The other interesting thing about this strategy is that you build the bracket “inside out”.  That means you start with the champion and work your way back to the first round.  Let’s get started.


The most likely champion according to the simulation is Kansas.  The problem is that the most popular championship pick is also Kansas.  Other popular choices include Michigan State, North Carolina, Oklahoma, and Kentucky according to ESPN’s Tournament Challenge entries. Coming in at 6th on that list is my contrarian pick to win the championship.  Currently only 4.5% of brackets are picking Virginia to win the title, but the simulation has them as the 2nd most likely champion at 12.8%.  The Cavaliers cutting down the nets is the perfect contrarian pick to get our bracket started.


Using the same method as before, we’re ignoring some of the fan favorites and going with other teams that have a higher probability percentage than fans are currently picking.  Joining Virginia in the Final Four will be Oregon (22.4%), Villanova (20.3%), and West Virginia (16.6%).

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While this is a contrarian bracket, look at the Final Four picks.  You still end up with two 1-seeds, a 2-seed, and a 3-seed.  Again, the idea isn’t to go batshit crazy and pick a bunch of high seeds, just to differentiate yourself from the rest of the field while still having a chance to win.


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Using that same method throughout the bracket, this is how the South region winds up.  Even though Kansas is a popular pick, the simulation still likes them enough to get to the elite eight. Maryland, California, and Arizona are all being “overpicked” in the first round and thus the upsets are worth taking to try to gain some points against the rest of the field.  Iowa is a team that the public is not picking enough as the simulation has them advancing past Temple 74.2% of the time.


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There are fewer first round upsets in this region but still some surprises.  After winning the SEC championship on Sunday, Kentucky is again a public darling but Indiana has a better chance then the public thinks.  Currently 30% of users on ESPN are picking North Carolina to go to the Final Four so picking a very capable Hoosier team against them is a great chance to gain some points on the field.


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It’s not a surprise that Duke is a popular pick but I was surprised at the high percentage for Baylor, especially considering the public perception of the sneaky 5 vs. 12 matchup.  The betting market agrees as Yale is currently only a 6-point underdog.  Texas is an underdog to both Texas A&M and Oklahoma, but they are underpicked enough to pencil them in through to the Elite Eight.


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Much like Kansas in the South region, Michigan State is going to be the most popular pick to win this region.  They are too good to pick against early on in the tournament so they still win three games.  Purdue is a very popular first round pick with 89% of early entries taking the Boilermakers.  This is a perfect scenario to take the 12-seed as many of those brackets have Purdue winning two or even three games.

There is your complete contrarian bracket to try to take down the big tournament pool.  Feel free to make a few adjustments to make the bracket your own, just remember to stay away from the tournament favorites if you want to win the whole thing.