Winning Your Bracket Takes More Than Picking Who You Think Will Win - Game Theory 2023 March Madness

Most people approach filling out their brackets by asking themselves the question, "who will win this game?" for each match-up until they reach a final winner. However, this strategy may not be optimal for larger office pools with 50 or more entries. In smaller pools, it's better to stick with the favorites as indicated by the odds on a sportsbook like Draftkings or Fanduel. But in larger pools, it's important to strike a balance between picking favorites and selecting upsets based on historical data and trends.

For this article, I will assume you are in a larger office pool of 50+ entries. If you are in a smaller one, you will want to be as chalky as possible.

Step 1
Number of Entries
For those participating in pools that permit multiple entries, it's advisable to enter enough times to occupy 2-5% of the total entries. In my experience, playing in a pool with 100-125 entries, I typically submit 5 entries. This approach not only increases the likelihood of winning but also provides the chance to diversify the picks.

Step 2
Looking for Value
After transitioning into a daily fantasy sports professional seven years ago, I recognized the significance of player ownership. Although one cannot predict the ownership of each player in an NBA slate with certainty, experience allows for reasonable estimation. The importance of this information lies in its ability to reveal whether a player is overvalued, undervalued, or valued appropriately by the market. This same concept can be applied to filling out a bracket with greater ease.

The following is the process for using models to predict a team's likelihood of reaching the final four or winning the championship. There are multiple reliable models available, such as 538, Kenpom, or futures lines from a sportsbook like Draftkings or Fanduel. When utilizing futures odds, one must account for the "juice," which is not an exact science for futures. This article will use the numbers from 538 as an example.

Here is the list of each team with their 538 Probability vs. ESPN percentage to win their region (get to the final 4)

Some of the best leverage plays to make the final 4 are Kentucky, Michigan St, Providence, and Tennesee in the East. If you read my article on eliminating contenders you know we eliminated the top 4 seeds in the East. This could be a bracket you want to take a longshot. The leverage is there as well, at least using the 538 model.

In the Midwest Houston is being picked at a rate pretty close to what the 538 model thinks their probability is to make the final 4. At +160, the market is not as high on Houston as the model. The team that is being overvalued is Texas, according to 538. You can go with just about any other team and get some leverage on the field. Taking a chalk Houston is not terrible if you are differentiated elsewhere.

In the South, the model loves Creighton, which is skewing the data a bit. Baylor, SDSU, and Virginia aren't terrible, but the best bang for the buck may be Arizona, even though the model has them on the market right now. If you trust 538, Creighton would be a unique play for sure. You will likely win the pool, or at least cash, if they make the Final 4 and you have it correct. In my pool, you are multiplying six by the points for that round. The model puts it at +810 while the market is paying +750. The more I look at it, they are going to be well worth the gamble. You are 8 or 9 to 1 to get them to the Final 4, and you will likely win a 100-entry pool.

In the West Gonzaga and UCONN headline the best leverage plays. Kansas is way overvalued. Being the defending Champion and being Kansas, that isn't a shock. In the article I posted about eliminating contenders, UCONN would now be eliminated based on Rule #1. They are currently top 10 in AP and were not ranked pre-season. When I wrote the article, the new AP had not been released.

Here is the list of the top teams with their 538 Probability vs. ESPN percentage to win the National Championship

There are many ways to use this information. Your league rules will determine a lot of it. In my pool, we multiply seeds by the pts for the rd. That gives some reward for picking upsets. If your pool is strictly giving points for wins, then you may want to be a little more chalky with your picks. Ultimately your best chance of winning a large pool is to strategically differentiate yourself with high probability picks that are being underplayed.

If you live in an area where the entire pool will take the home team then you are in the best possible pool to be in. You are at a huge advantage if you are in Tuscaloosa, AL and everyone will be taking Alabama. Then you just go with Houston and hope for the best. But in an average pool, you should use the ESPN data.


Step 3
Work Backward
I like to figure out my champion and final 4 before filling out my bracket. If I have a chalky Final 4 then I better be taking some more risks early in the tournament. In a "seed bonus" type pool, you will want to take a lot of higher seeds to advance deep.

Conversely, if I take Creighton and Kentucky in the Final 4, one of them will have to advance to the Championship Game. If you go this route you will want to be pretty chalky in the earlier rounds of the bracket. You are taking all of your risk later. Remember, you are really only competing with the others who have Creighton Or Kentucky. That will be a much smaller percentage of your pool, so being chalky may be good enough to get you out in front of them.

If you have a 2 or 3 seed losing in the 2nd round then take them to lose the first game in a pool that rewards upset picks. I have picked up a cheap 15 points quite a few times by fading 2 seeds that I did not think would go far in the tournament. My risk is 2 points to the field to win 15, but I will do this more when I have a chalky final 4. This is why you must work backward.

For brackets that are taking one or more high seeds in the Final 4 then you should advance all favorites(vegas favorites) as far as they will go. If you want a Creighton and Kentucky Final 4 then there is no need to choose one to win it all. If one makes the Final 4, as I said earlier, you are likely to win the pool. To make sure you are getting the highest probability of points to go with it, you will want to take Houston to win the whole thing.

There are so many ways to play the brackets. What I want to get across is using game theory is more important than knowing college basketball. I have a tremendous cash rate in the pool I have been running for over 20 years. I play 5 entries each year, we have about 125 entries, and I have taken first about 4 or 5 times and finished top 5 to cash almost every other year.

I would love to hear your thoughts in Discord about how you are playing it.

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