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2020 Yankees Prospect Madness Heads To 2nd Round

Over the past week, we have finished the 1st Round of 2020 New York Yankees Prospect Madness. In case you don’t remember the process to putting together this tournament, we took some of the top Yankees prospects from the past 10-15 years and put them in a 32-player field divided into 4 regions.

We have an updated bracket available for you below as the 2nd Round of voting gets underway on Thursday. You will get to vote on one region per day on our Twitter account (@PinstripedPros) to determine which players make their respective regional final. Remember that the winner of the Cashman Region will face the Oppenheimer Region winner. On the other side of the bracket, the Afterman Region winner will face the victor of the Rodman Region.

We apologize if the bracket looks different this time around, but this is currently how the tournament stands.

Let’s give you a summary of how the voting went down in each region for Round 1.

Cashman Region

The Cashman Region did not provide many upsets and was all chalk as it heads to Round 2 where you will get some interesting matchups. (1) Gleyber Torres and (2) Luis Severino both received over 90 percent of the vote to win their matchups. Meanwhile, (3) Joba Chamberlain and (4) Austin Romine got more than 80 percent of the vote in their wins.

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In the next round, Torres will go up against Romine and it will be a battle of pitchers as Severino takes on Chamberlain. Severino vs. Joba is a fun matchup because of the sensation around Chamberlain in 2007 against how Severino rose up to be the top pitching prospect in this new era of Yankees baseball.

Oppenheimer Region

The Oppenheimer Region brought about the first upsets of the tournament. While the top two seeds, (1) Aaron Judge and (2) Tyler Austin rolled in their respective matchups, (6) Jasson Dominguez upset (3) Deivi Garcia in a battle of current Yankees prospects. The 4-5 matchup between (4) Jorge Mateo and (5) James Kaprielian came down to the wire, but Kaprielian barely got the win to advance.

In the second round, Judge will take on Kaprielian in a battle of two former first round picks in the Yankees organization. In the second matchup, Austin battles Dominguez. It will be a tough draw for Austin as Dominguez could be that lower seed that makes a deep run in the tournament without even playing a professional game yet.

Afterman Region

It was mostly chalk in the first round of the Afterman Region as the top 3 seeds each received over 80 percent of the vote in their respective matchups. In particular, the top 2 seeds, (1) Gary Sanchez and (2) Miguel Andujar, each received at least 95 percent in the poll.

There was one small upset as (5) Estevan Florial pulled out the win over (4) Tyler Wade as the current Yankees prospect advances to Round 2.

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Round 2 in this region will be two battles of past prospects vs. current prospects as Sanchez takes on Florial and Andujar takes on the third seed, Phil Hughes.

Rodman Region

Finally, the Rodman Region had one upset in its four matchups. In a battle that came down to the wire, (6) Slade Heathcott upset (3) Blake Rutherford to advance to Round 2. As for the other top seeds, (1) Jesus Montero, (2) Dellin Betances, and (4) Clint Frazier each got at least 65 percent of the vote in their matchups.


Round 2 in this region could see one upset as Montero takes on Frazier. Montero was the top prospect for the earlier part of the 2010s and Frazier was a top prospect in the Yankees system since coming over in the Andrew Miller trade.

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The other matchup is Betances vs. Heathcott. While both players made it to the Major Leagues, neither of them were teammates in their minor league careers.

Written By

I am an alum of St. John's University, where I majored in sports management.

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