Over the past few offseasons, the Yankees have been notoriously delayed in their approach when it comes to big-name free agents. Whether or not it’s a tactic that GM Brian Cashman uses to gauge the open market before extending what he and Hal Steinbrenner feel is a fair offer, this winter could mark a turning point for the future of the Bombers.
With many of their young stars either still outside the window of arbitration or just now entering it, there will soon come a time when the Yanks are forced to extend the likes of Aaron Judge, Gary Sanchez and Gleyber Torres — each for enormous paydays.