The Phillies know exactly when their offseason will truly begin. They just don’t know when that moment is going to arrive.
With the Winter Meetings set to open a week from today in Orlando, the Phillies find themselves in an unusual holding pattern. The entire shape of their winter, their lineup construction, their spending appetite, even their level of urgency, hinges on the outcome of one decision that hasn’t come yet.
Kyle Schwarber.
There has been mutual interest from the start. Both sides have made it clear for weeks that a reunion is the preferred outcome. Rival clubs expect it. Industry voices expect it. Even some agents are preparing for it. Yet nothing appears imminent, and until the Phillies know whether Schwarber is returning, they’re operating without the clarity they need to move forward.
The most recent indication of where things stand came from MLB.com’s Todd Zolecki, who reported last week that the Phillies and Schwarber are “not close to a deal.” That doesn’t mean talks have broken down, or that negotiations have turned cold. It simply underscores that there is still distance to cover, and that there is no timetable for when that distance might be closed.
Schwarber’s camp knows exactly what kind of market they have after a 56-home run season, the kind of season that resets expectations and makes teams rethink budgets. Only 23 players in the history of the sport have ever hit 56 or more. Most of them, understandably, were not looking for their next contract in their age-33 season. Schwarber is.
He has drawn public interest from the Red Sox, Orioles, and Pirates. The Reds - in Schwarber’s native Cincinnati - have been floated as a possible suitor as well. The Phillies remain the most natural fit, but the presence of multiple teams in the wings gives Schwarber something he has rarely held in his career: leverage.
That leverage is why this is taking time. And that leverage is also why the Phillies largely can’t proceed with their offseason until answers arrive.
The Phillies won’t say Schwarber is their top priority, but the offseason roadmap leaves little room for debate. J.T. Realmuto’s situation remains important, and the club continues to explore trade possibilities for Nick Castellanos, but Schwarber is the pivot point. His contract size, his role, and his roster function dictate how the Phillies will approach everything around him.
Do they need left-handed power?
Do they need a middle-order presence?
Do they need to reallocate payroll into two or three smaller pieces?
Those are fundamentally different scenarios, and the Phillies can’t prepare for all of them at once.
That uncertainty trickles into how aggressive they’ll be next week in Orlando. Winter Meetings tend to generate momentum across the league, the deals that don’t happen there can set up the deals that do happen later. For the Phillies, that momentum may be limited until Schwarber’s path becomes clear.
The risk for the Phillies is obvious. If this stretches into late-December or beyond, other free agents will come off the board. The middle-tier bats will sign. Some market inefficiencies will evaporate. And should Schwarber ultimately land elsewhere after a patient, deliberate process, the Phillies could find themselves scrambling to reassemble a Plan B with fewer pieces available.
Philadelphia’s front office is aware of that risk. So are rival agents. In fact, some may be advising their clients to wait, just in case the Phillies suddenly pivot from “running it back with Schwarber” to “full-scale search for a replacement middle-order hitter.”
But the Phillies also know that Schwarber’s timeline isn’t something they control. They faced a similar dynamic two years ago when Aaron Nola entered free agency. That negotiation concluded quickly - within two weeks - because both sides wanted stability. This situation is different. Schwarber’s market is larger. His production changes calculations. And the Phillies, of all teams, understand what he means to their offense, their clubhouse, and their identity.
That’s why the early quiet shouldn’t be confused for trouble. The Phillies are willing to wait. Schwarber is willing to listen. And the industry still expects the two sides to eventually find the middle ground that has eluded them so far.
But until it happens, this remains the story of the Phillies’ winter: a powerful team idling on the runway, engines humming, waiting for the signal to take off.
Whether that moment arrives before the Winter Meetings - or sometime after - will determine what kind of offseason this becomes.
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