Brian Cashman has been the Yankees General Manager since 1998. Cashman’s first three seasons as GM produced three World Series Titles, something that had never been done before in MLB history. During his time as GM, the Yanks have constantly been atop the AL East and have not finished a season under .500.
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.
This post details Cashman’s top five trades of the past five years that effectively retooled the organization into a flexible, cost-effective, and youth-filled roster. The players on this list are obviously not homegrown because of the trade that brought them to New York, but what should be recognized is the vision and ability of Cashman and his staff to pinpoint overlooked, underappreciated, players that have a higher upside and ceiling than the industry values them at.
Some honorable mentions to this list are: (1) acquiring Nathan Eovaldi, Garrett Jones, and Domingo Germán for Martin Prado and David Phelps, (2) acquiring Starlin Castro for Adam Warren, (3) trading Justin Wilson for Chad Green and Luis Cessa, and (4) acquiring Luke Voit for Chasen Shreve and Giovanny Gallegos.