The New York Yankees are confronting significant offseason decisions following their disappointing playoff loss, swept in the American League Division Series by the Tampa Bay Rays. This outcome has intensified scrutiny on manager Aaron Boone’s future and placed considerable pressure on the front office to make strategic roster moves. Among the pressing questions are how to handle free agency for key players, notably closer David Bednar and second baseman Jazz Chisholm Jr.

Inside sources, including Yankees insider Jon Heyman, indicate the team plans to offer Bednar a qualifying offer valued at $23.15 million. Bednar had a strong 2026 season, making him a valuable asset to retain, either by having him accept the one-year deal or potentially securing compensation if he signs elsewhere while pursuing a longer contract. This move would reflect the Yankees' intention to maintain a reliable late-inning presence in their bullpen.

In contrast, the Yankees appear unlikely to extend the same qualifying offer to Chisholm after a disappointing season in 2026. Despite Chisholm’s stellar 2025 campaign that included a 30-30 season, his inconsistencies this year have led the club to doubt his fit going forward. Although Chisholm has expressed a desire to return to New York, the organization’s leadership seems prepared to move on from him, signaling a potential shift in their infield plans.

These different approaches towards Bednar and Chisholm underscore the Yankees’ broader evaluation following their playoff exit. While they seem committed to securing Bednar as part of their bullpen strategy, the second base position remains uncertain. How the Yankees resolve these free agent questions will be pivotal in shaping the team’s composition and direction heading into the 2027 season.