For all of Cashman’s brilliance during the late ’90s, early 2000’s, and that memorable 2009 season, some of his best work as Yankees GM has come in the last five years. With an aging, injury prone roster filled with bad contracts, Cashman and Co. knew they were at a crossroads.
By 2014, analytics had become increasingly more valued and utilized within the game; creating a whole new way General Managers could—and should—operate in terms of constructing an organization from the Major League roster all the way down to rookie ball. Over the past five seasons, Cashman has completely reconstructed the Yankee organization based on the cultivation and stockpiling of young, high-upside talent instead of the constantly overpaying and trading away young talent for aging stars.