The annual MLB Winter Meetings are almost upon us. With the league gathering next week, from Sunday evening through Thursday morning, there is sure to be plenty of news, rumors, trade and free agent signings coming out of Orlando, Florida.
A contingent from the Philadelphia Phillies will join all the other league and team executives, owners, managers, agents, players, scouts, and media members for the offseason's biggest event that should kickstart the action.
Speaking of kickstarting, the Phillies could use something to shock their offseason to life. Thus far, the front office has left fans in a dreary, seemingly never-ending haze of rumors and speculation. We're now over one month into the offseason and the biggest moves have been the minor league signing of Bryan De La Cruz and claiming the tantalizing Pedro León off waivers.
But with the Winter Meetings, it's time to see some action. Here's what the Phillies need to do in the upcoming week to give fans something to get excited about.
3 big Winter Meetings moves Phillies need to make to kickstart their offseason
No. 1: Re-sign Kyle Schwarber
You obviously saw this one coming. Re-signing Kyle Schwarber is top of mind for Phillies fans and the front office. Phillies president of baseball operations Dave Dombrowski hasn't been coy about his top priority. The Phillies still have a competitive window left with their veteran core and keeping Schwarber in the lineup has to be a key piece of that plan.
Coming off a career year, is the soon-to-be 33-year-old designated hitter likely to hit an NL-best 56 home runs again or lead the majors with 132 RBIs? Probably not. It will be nearly impossible to replace his offensive production at the top of the lineup, however. It will be even harder to replace his clubhouse leadership.
Signing Schwarber to what will presumably be a five-year deal worth at least $150 million might not look great by the end of the contract. But his free agency at this juncture of their window has put the Phillies between a rock and a hard place. This has to be their biggest move of the offseason, and with competitors lurking in the weeds it's time to get something done.
No. 2: Re-sign J.T. Realmuto
But wait, not so fast! Catcher J.T. Realmuto, another veteran piece who the Phillies are trying to bring back, might be even more important for the next couple of seasons of contention. Considering how well he handles the pitching staff, Realmuto might be even harder to replace than Schwarber.
Heading into his age-35 season, rumors are that he's looking for a two-year deal. That should make this re-signing a no-brainer for the Phillies. Unfortunately, based on the lack of catching options on the free agent market, Realmuto surely has plenty of teams interested in his services.
Even though he just had his worst offensive season since he broke into the league, Realmuto is more important to the Phillies than to any other suitor at this point. So, expect Dombrowski and company to seal the deal soon.
Trade Nick Castellanos
This move might be more of a case of addition by subtraction. Everyone knows that the Phillies are trying to move Nick Castellanos this offseason and that his time in Philadelphia is over. The problem is that finding a trade partner might be tough.
He'll be 34 before Opening Day, is due $20 million next year, was one of the worst defensive outfielders in 2025, and posted a career-low -0.6 fWAR. Getting another front office to take on at least some of Castellanos' remaining salary would be a win for the Phillies.
The sooner they can figure it out, the sooner they will have a clear way forward to rebuild the outfield for 2026. If they can't work out a trade, they will be forced to release him and eat his salary.