Presenting the Yankees’ 25 Smartest Moves of the Past 25 Years

As Pinstripe Alley wraps up its series on the Yankees’ 27 championship teams this week, Major League Baseball shows few signs of ending its lockout of the players anytime soon. It’s disappointing, but thankfully, our chosen ballclub has an extremely rich history to explore as we pass the time amid our other articles.

So today, PSA will begin a new series detailing the Yankees’ 25 smartest moves of the past 25 years (nearly all of current GM Brian Cashman’s tenure). The degree of intelligence behind each transaction is quite subjective, so I enlisted 12 other staff members to help out in the selection process. Note that none of these nominees are draft selections like Aaron Judge, or amateur international free agent signings like Luis Severino because I had to draw a line somewhere, and with players that young, the odds of a “smart” move going bust are even higher. Also, we will not be ranking the 25 moves, as that is an even more arbitrary endeavor, and it was difficult enough for us to narrow down the chosen transactions from a list of 40 nominees.

Instead, we’ll simply be going in chronological order with the 25 moves that were chosen the most among the staff who participated. There were some tough omissions, but then again, 25 years is a lot of time for plenty of well-executed transactions to be pulled off. For example, I have a particular fondness for both the out-of-nowhere Bartolo Colón signing in 2011 and Cashman acquiring steady starter Brandon McCarthy in July 2014 for Vidal Nuño, but neither addition made the cut.

We won’t spoil which 25 transactions made our list just yet, but as each one is revealed, links will be added to this master post. We’ll begin today with Jon discussing the landmark signing that brought Orlando “El Duque” Hernández to the Bronx from Cuba in 1998. Look for each subsequent post to come every weekday!

3/23/1998 - Orlando Hernández signed
6/29/2000 - The David Justice trade
12/7/2000 - Mike Mussina signed
2/9/2001 - Derek Jeter extended
2/17/2001 - Mariano Rivera extended
2/3/2002 - Jorge Posada extended
12/19/2002 - Hideki Matsui signed
2/16/2004 - The Alex Rodriguez trade
1/3/2006 - Johnny Damon signed
7/30/2006 - The Bobby Abreu trade
1/25/2008 - Robinson Canó extended
11/13/2008 - The Nick Swisher trade
12/11/2008 - CC Sabathia signed
12/8/2009 - The Curtis Granderson trade
1/22/2014 - Masahiro Tanaka signed
12/5/2014 - The Didi Gregorius trade
12/5/2014 - Andrew Miller signed
12/9/2015 - The Chad Green trade
2/6/2016 - Jonathan Loáisiga signed
7/25/2016 - The Gleyber Torres trade
7/19/2017 - The 2017 White Sox trade
12/9/2017 - The Giancarlo Stanton trade
8/4/2018 - The Gio Urshela purchase
1/14/2019 - DJ LeMahieu signed
12/10/2019 - Gerrit Cole signed

Best of the Rest

11/18/1997 - The Scott Brosius trade
2/18/1999 - The Roger Clemens trade
1/26/2011 - Bartolo Colón signed
11/11/2015 - The Aaron Hicks trade
7/27/2018 - The Luke Voit trade