The Philadelphia Phillies are preparing for the upcoming Winter Meetings in Orlando, Florida, as they look to address several key issues with their roster. After surprising many by reaching the World Series in 2022 and making significant signings at that year’s Winter Meetings—including Trea Turner, Taijuan Walker, and Matt Strahm—the team is still seeking its third championship.
This offseason, the Phillies’ primary focus has been on re-signing two core players from their recent seasons: Kyle Schwarber and J.T. Realmuto. Both remain unsigned as the meetings approach. According to sources, negotiations between the Phillies and Schwarber have not progressed significantly, but a deal could develop quickly. ESPN has reported that it would not be surprising if Schwarber chooses a new team before the end of the Winter Meetings, with teams such as the Mets, Orioles, Reds, and Pirates reportedly interested in him. However, there is still an expectation that he may return to Philadelphia.
Realmuto’s future with the Phillies is also uncertain. The Red Sox have shown interest in signing him due to his leadership qualities and defensive skills behind the plate—attributes valuable to any playoff contender—even though his offensive numbers have declined recently.
If either or both players do not return, the Phillies will need alternative plans. Even if they are re-signed, additional work remains for the front office. The team hopes to bring back outfielder Harrison Bader while considering moving on from Nick Castellanos through a trade or release. They are also seeking another right-handed reliever for late-inning situations.
On potential trades, while top prospects Andrew Painter, Aidan Miller, and Justin Crawford are considered important for maintaining affordable young talent on the roster—and thus less likely to be traded—the club may instead look at trading current major league players such as Castellanos (as a salary move), Alec Bohm, Brandon Marsh, Bryson Stott, Strahm, or Orion Kerkering.
Regarding prospects who could impact next season’s roster: Painter has a strong chance of making Opening Day if Zack Wheeler is unavailable; Crawford appears likely to join but has yet to receive confirmation from president Dave Dombrowski; Miller may contribute later in 2026 after learning new positions beyond shortstop; Gabriel Rincones Jr., mentioned by Dombrowski as a possible contributor in 2026, faces challenges against left-handed pitching.
For this year’s Rule 5 Draft protections were extended to Painter, Rincones Jr., and pitcher Alex McFarlane. Unprotected candidates who might be selected include pitchers Griff McGarry, Saul Teran and Andrew Baker; infielder/outfielder Felix Reyes; and catcher Caleb Ricketts.
A central question remains whether Philadelphia will largely retain its current group or make substantial changes through trades this winter—a decision complicated by examples like the Mets’ recent trade of Brandon Nimmo for Marcus Semien as teams recognize when change is necessary even at personal cost.
