Following the conclusion of the World Series, five Pittsburgh Pirates players, including fan favorite Andrew McCutchen, have entered free agency. McCutchen, who expressed a desire to return, had a solid season with 20 home runs and a .232 batting average. Alongside him, relievers Aroldis Chapman, Jalen Beeks, Ryan Borucki, and catcher Yasmani Grandal have also opted for free agency. Pirates general manager Ben Cherington and manager Derek Shelton have shown interest in retaining McCutchen, emphasizing his leadership and performance. Chapman's return is plausible due to his role as the unofficial closer, although financial considerations may affect that decision. The Pirates, with the most free agents in the National League Central, must navigate these negotiations within five days before other teams can engage.