5 biggest questions Yankees are facing during 2026-27 MLB offseason

Following an ALDS sweep by the Tampa Bay Rays, the New York Yankees enter the 2026-27 offseason confronting several roster and managerial issues. Aaron Boone is expected to remain manager despite outside criticism, having received support from players like Aaron Judge and Cam Schlittler. Meanwhile, the offense struggled severely in October, batting .130 across the postseason exit while dealing with Judge's regular-season injury absence.

Anthony McCarron argues that New York faces pivotal roster decisions, particularly regarding pending free agent infielder Jazz Chisholm Jr. and relievers David Bednar and Paul Blackburn. McCarron asserts that the Yankees must prioritize re-signing Bednar and address persistent defensive miscues that have repeatedly plagued the club in recent postseasons.