Chicago White Sox face roster and financial decisions for 2027

The Chicago White Sox front office faces significant decisions regarding player retention and roster construction heading into the 2027 season. A primary concern is the status of pitcher Luis Castillo, who struggled with an 8.42 ERA during the final stretch of the 2026 season before being demoted to the bullpen and eventually placed on the injured list.

Castillo remains a significant financial obligation, with $24 million owed for the upcoming season and a potential $25 million vesting option for 2028. Analysts suggest the team could either hope for a performance recovery or attempt to trade him while absorbing a portion of his salary to reallocate funds toward top-of-the-rotation starters.

Additionally, the team must evaluate impending free agents. Sean Newcomb, who recorded a 3.09 ERA across 90.1 innings in 2026, is a key figure the organization may struggle to retain due to expected salary increases. Randal Grichuk also exceeded expectations after signing a low-cost contract in May, adding to the complexity of the team's offseason planning.