The 2021 MLB First-Year Player Draft is a little over a month away. Over that time period, we at Pinstriped Prospects are going to be bringing you draft profile on possible selections the New York Yankees could make throughout the three-day process that will go 20 rounds this year. First off, though, let’s look at the history of where the Yankees will pick in the first round, which is at the 20th selection.
The 20th pick is the highest the Yankees have picked in the first round since 2017 when they took right-handed pitcher Clarke Schmidt with the 16th pick. While Schmidt has battled injuries over the course of his professional career, he has at least made it up to the big leagues, which is a rarity for most Yankees draft picks over the last decade.
In fact, since 2010, only three Yankees that were selected in Round 1 have appeared in a big league game. Those three players were Schmidt, outfielder Aaron Judge (2013), and RHP James Kaprielian (recently made his big-league debut with the Oakland Athletics).
As for the 20th pick, the Yankees have only made that pick once in their franchise history. That was back in 1996 when the team selected a left-handed pitcher from the University of Maryland named Eric Milton. Milton ended up being traded from the Yankees to the Minnesota Twins in February 1998 along with three other players in a deal that sent second baseman Chuck Knoblauch to the Bronx.
If you look at the recent history of this pick across Major League Baseball, the 20th pick has produced some major leaguers. Since 2010, five players have made their big league debut from that selection. If you stretch out the sample size to 2000, that number increases to 14 players. Some of the players you may be familiar with include Denard Span (2002), Trevor Plouffe (2004), Gavin Lux (2016), and David Peterson (2017).
In terms of recent first round picks by the Yankees, they have selected a position player in three of the last four years. The only pitcher they have selected in Round 1 since then was LHP T.J. Sikkema with the 38th pick in 2019 (second first round pick), which they acquired in the deal that sent Sonny Gray to Cincinnati
Last year, New York took Austin Wells, which was the second catcher they have taken in the last three years. Do they take another catcher this year as the best player on their board or with not as many affiliates in the system, do they go in a different direction such as adding another arm? We will examine all of those possibilities over the next few weeks.

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