President of Baseball Operations Buster Posey enters his third offseason with the San Francisco Giants facing a difficult combination: a 97-loss team, an expensive veteran core, and an expectation of contending in 2027. His next set of decisions has to reconcile all three.
Posey has already made his position clear. Discussing the Giants' 2027 expectations , he said, "I do believe that we can." That confidence makes this potentially the most important winter of his tenure. A roster built around favorable health outcomes and veteran rebounds would leave the same vulnerabilities.
San Francisco Giants third baseman Matt Chapman celebrates with shortstop Willy Adames. | IMAGN IMAGES via Reuters Connect
The Giants' commitments include Rafael Devers through 2033, Willy Adames through 2031, and Matt Chapman through 2030. Logan Webb's current deal runs through 2028. Those contracts provide continuity, but productive years cannot be banked indefinitely.
Webb and Devers will both be 30 on Opening Day in 2027, while Chapman turns 34 in April. The front office has invested heavily in a group whose opportunity to win together requires immediate support. Waiting for the next wave of prospects carries a cost when established players are getting older.
Devers hit 37 home runs with a .258/.340/.525 slash line in 2026. That production gives Posey an offensive foundation worth supporting. Adding dependable innings would give the Giants a better chance to turn that investment into meaningful September games.
The financial choices will be consequential. Giants On SI's payroll breakdown estimates roughly $153 million committed to seven veterans for 2027, before arbitration and the rest of the roster are accounted for. That estimate is a starting point for evaluating flexibility, with ownership's eventual budget determining how much Posey can add.
Every retention decision should therefore consider the player's role, health, and replacement cost. Keeping a familiar veteran needs to advance the roster plan enough to justify the money and roster spot.
San Francisco Giants President of baseball operations Buster Posey. | IMAGN IMAGES via Reuters Connect
Posey has acknowledged that the front office overestimated its bullpen, which finished 2026 with a 4.14 ERA and 27 blown saves. Accepting responsibility should change how the Giants evaluate the next group of pitchers.
His stated offseason pitching priorities need to yield established rotation help and multiple dependable relievers. Four young starters underwent Tommy John surgery in 2026. The Giants need contingency plans that can cover innings while those pitchers recover and sustain the staff through injuries or poor performance.
That urgency should also produce a more coherent development plan. Bryce Eldridge needs everyday work, and young outfielders need jobs they can earn. Veteran additions should complement those opportunities. Posey must give the coaching staff enough usable options to reward performance and adjust when an initial plan fails.
Trading prospects can be part of the answer. The front office should consider moving players with limited paths to San Francisco for pitching that helps beyond 2027, while preserving enough upside to support the next competitive roster.
A successful Giants offseason should be visible before the standings offer a verdict. By spring training, the roster needs dependable innings, defined roles, and depth that can survive setbacks. Posey has asked fans to believe contention is realistic. This winter, his front office must give them evidence.
This article was originally published on www.si.com/mlb/giants/onsi as Why This Could Be the Most Important Offseason Yet for the Giants Front Office .
