The Philadelphia Phillies are preparing for the upcoming Winter Meetings in Orlando, Florida, as they continue efforts to secure key players and address roster needs. The team has not yet added a third World Series title since their 2022 postseason run, which saw them clinch a playoff spot late in the season and advance to the championship series.
In previous offseasons, the Phillies made significant moves at the Winter Meetings, such as signing Trea Turner, Taijuan Walker, and Matt Strahm after their 2022 campaign. This year, their focus is on re-signing outfielder Kyle Schwarber and catcher J.T. Realmuto, both of whom remain unsigned as negotiations continue.
Sources indicate that talks between the Phillies and Schwarber have not reached an agreement, but there is speculation he could make a decision before the end of the Winter Meetings. Several teams including the Mets, Orioles, Reds, and Pirates are reportedly interested in him. Despite outside interest, many expect Schwarber to return to Philadelphia.
J.T. Realmuto’s future with the team is also uncertain. The Red Sox have shown interest in acquiring him due to his experience and defensive skills behind the plate. While retaining Realmuto is seen as likely by some observers, there are no guarantees he will re-sign with Philadelphia.
The Phillies are also exploring options beyond Schwarber and Realmuto. They hope to bring back Harrison Bader for outfield depth and may look to move Nick Castellanos through trade or release. Additionally, adding a right-handed reliever for late-inning situations remains a priority.
Potential trades could involve current roster members if changes are needed for next season. Players such as Castellanos (possibly as a salary move), Alec Bohm, Brandon Marsh, Bryson Stott, Strahm, or Orion Kerkering might be considered trade candidates this winter.
Top prospects Andrew Painter, Aidan Miller, and Justin Crawford are viewed as important pieces for Philadelphia’s future; management prefers not to trade them unless necessary. Painter has a strong chance of making the Opening Day roster if Zack Wheeler is unavailable at the start of next season. Crawford is also expected to join the team soon while Miller may contribute later in positions other than shortstop after further development.
Outfielder Gabriel Rincones Jr., mentioned by Dave Dombrowski as a possible contributor in 2026, continues working on his performance against left-handed pitching in the Minor Leagues.
For next week’s Rule 5 Draft, Philadelphia protected Painter, Rincones Jr., and pitcher Alex McFarlane from selection by other clubs but could lose unprotected players like Griff McGarry or Felix Reyes.
The main question facing management is whether to keep much of last year’s roster intact or pursue more substantial changes through trades—a decision that could require moving established players to create a new mix ahead of 2026.
