The offseason has been quiet so far for the Philadelphia Phillies. No major-league free-agent signings. No trades to boost the roster. No real action to this point.

But the Phillies have earned a reputation as big spenders in recent years, and the club has holes to fill and marquee names to retain or replace. The team’s president of baseball operations Dave Dombrowski will be busy. Could the upcoming Winter Meetings in Orlando, Fla., be the start of it?

Starting Sunday, with official team business taking place from Monday through Wednesday, executives, agents and other figures across Major League Baseball will gather for the annual offseason event. The Winter Meetings will accelerate a lot of the action in some years. And there’s a chance that happens in 2025.

Philadelphia’s most notable free agent, Kyle Schwarber, could sign by the end of the Winter Meetings, ESPN’s Jeff Passan recently reported. After finishing as the runner-up for National League MVP this year, Schwarber is one of the very best bats on the market, and keeping him is a priority for the Phillies. If he indeed signs this upcoming week, the Phillies will either know that their star slugger will remain in the organization or that they’ll need to start working on Plan B. Schwarber’s decision will be pivotal, and it could come soon.

The last real splash the Phillies made at the Winter Meetings was signing shortstop Trea Turner to an 11-year contract in 2022. Reaching another deal with Schwarber could be their next. Additionally, it will be worth monitoring the statuses of J.T. Realmuto, Harrison Bader and Ranger Suárez, all important 2025 Phillies who are currently free agents.

Moving On?

Perhaps the Winter Meetings could provide a setting for the Phillies to find a trade partner for Nick Castellanos, the outfielder who appears destined to end up on another team in 2026. Philadelphia will likely have to eat most of his remaining $20 million in any swap.

Castellanos had a career-worst year in 2025 with a .694 OPS in 147 games. He struggled defensively in right field. He was frustrated by a loss of playing time down the stretch, and both the Phillies and the player could benefit from a departure. But will a team willing to trade for him emerge?

A third baseman earlier in his career, Castellanos expressed an openness to move to first base if asked to do so in an interview on MLB Network on Friday. Maybe that help boost his market to some extent if a club believes he can bounce back offensively while at a less demanding position. Ultimately, the Phillies could end up releasing Castellanos if they cannot put a trade together.

The Bullpen

At the Winter Meetings last year, the Phillies signed reliever Jordan Romano to a one-year deal, hoping the Canadian right-hander could rebound from an injury-affected season with his hometown Blue Jays. The signing, to say the least, did not work out.

Romano had an 8.23 ERA in 49 outings, putting together one of the worst relief seasons in franchise history. But the Phillies could ultimately take another flier on an arm this offseason, and Orlando could be the place to do it.

While the team did add closer Jhoan Duran at the trade deadline, the bullpen felt an arm or two short by the time the postseason rolled around. The Phillies leaned on veteran David Robertson at the end of the year, and it doesn’t seem like he’ll be back at the start of 2026. José Alvarado could be a bit of a question mark after missing 80 games due to suspension and ending the year on the injured list. The Phillies could certainly afford to add to the relief unit at the Winter Meetings.

Winter Meetings Notes

• The Phillies coaching staff is not yet complete, as the club still has to hire a new bench coach. Additionally, Dombrowski said at his end-of-season news conference in October that the team has interest in signing manager Rob Thomson to an extension before the start of the 2026 season, Thomson’s last under contract. Dombrowski will surely be asked about the opening on the staff and Thomson’s contract in Orlando if there are no prior updates this weekend.
• The Rule 5 draft will take place on Wednesday. Pitcher Griff McGarry, the Phillies’ 2025 Paul Owens Award winner, could be a potential selection by another team, although it seems more likely he’ll end up back in the organization for another year.
• The Contemporary Era Committee will vote on an eight-player ballot for Hall of Fame consideration on Sunday. Barry Bonds, Roger Clemens, Carlos Delgado, Don Mattingly, Jeff Kent, Dale Murphy, Gary Sheffield and Fernando Valenzuela are the candidates. Murphy and the late Valenzuela briefly played for the Phillies during their careers.