
New York Yankees
Brian Cashman, senior vice president and general manager
+2.0 games
Cashman is the dean of MLB executives, having run Yankee front office operations since the 1998 season. That tenure includes 19 playoff appearances and four World Series titles, although none since 2009.
In an effort to end that World Series drought, Cashman’s front office made two dozen personnel moves affecting the team’s 2020 fortunes. The most headline-grabbing, most costly, and also the most influential obviously was the signing of free agent pitcher Gerrit Cole to a $324 million deal that extends through 2028.
Whether Cole was worth the pro-rated portion of the $36 million annually that the Yankees paid for him is a matter for CPAs to decide. But his 7-3 record and 2.83 ERA in a dozen starts did amount to a 1.5 game Wins Above Average contribution.
It’s also well to keep in mind that, from a pure money perspective, Cole’s 2020 value is not yet fully assessed. His most important contribution will be his ability, or lack of same, to lead the Yankees to that coveted World Series title the franchise has lacked for a decade now.
His victory in the playoff opener against Cleveland Tuesday night was a plus in that regard.
The annual short-term performance rating of Cashman’s front office for each of the past five seasons:
Season Games
2016: -1.4
2017: -0.7
2018: +4.6
2019: -2.0
2020: +2.0