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| The Phillies have plenty of questions heading into the winter. | CREDIT: IMGN Graphics & Photo |
“The pitching window is absolutely not closing. It’s not even closing an inch.”
Seven months later, after another October ended without a parade, Middleton may have been more right than it seemed.
And also wrong in a way that matters.
The Phillies still have a pitching window. Cristopher Sánchez just threw 207 innings with a 2.91 ERA. Jesús Luzardo finished with a 2.86 ERA. Andrew Painter is 23. Zack Wheeler remains one of baseball’s best starters. Sánchez and Luzardo have been secured deep into the next decade.
But the championship window we have spent four years talking about?
The one built around Bryce Harper, Kyle Schwarber, Trea Turner, Aaron Nola, Wheeler and the remnants of the 2022 pennant winners?
That window is closed.
That does not mean the Phillies cannot win the World Series in 2027.
It means they cannot enter another winter pretending the path toward winning it remains the same.
That is the distinction John Middleton and Dave Dombrowski must understand before they spend another dollar.
The 2026 Phillies went 88-74. They finished six games behind Atlanta, produced only a plus-15 run differential and went 31-38 against teams that finished .500 or better. Then, after needing Game 162 merely to secure a postseason berth, they scored nine runs in three Wild Card games and went home.
That wasn't simply an October malfunction.
It was a season-long warning.
Harper was still excellent, producing an .888 OPS. Schwarber still hit 44 home runs with an .870 OPS. But Turner fell to a .678 OPS. The Phillies no longer possessed enough lineup depth to assume their expensive veterans would simply overwhelm their deficiencies eventually.
So the Phillies’ first MUST this winter has nothing to do with a free agent.
Middleton must decide what he believes Dave Dombrowski's next job actually is.
Dombrowski is already signed through 2027. More important, this isn't occurring in a vacuum. USA Today reported in August that high-ranking Phillies officials expected Dombrowski to receive another extension this winter. Bob Nightengale reiterated in September that another extension was awaiting him.
That was before Atlanta ended the season.
Middleton should not extend Dombrowski simply as a reward for five consecutive postseason appearances.
If he extends him, it should be for something considerably more difficult:
Build the next Phillies contender while pieces of the current one still have value.
That is a fundamentally different assignment.
Dombrowski has spent most of his Philadelphia tenure adding to an established core. Now he must determine which pieces of that core still belong, which roles must change and which younger players need room to become something more than names on prospect lists.
That means the Phillies MUST stop treating continuity as inherently valuable.
They should not make a trade merely to create headlines. They should not dump productive players because fans demand blood after another failed October.
But they also cannot allow contracts, reputations or memories of 2022 to determine the 2027 lineup.
Justin Crawford needs runway.
Painter needs innings.
Aidan Miller eventually needs a path.
And the Phillies MUST NOT solve every opening by finding another established thirty-something veteran who makes them incrementally better today while making the next transition harder tomorrow.
For years, Philadelphia could justify that approach because every season felt like another swing at the same championship.
That championship team no longer exists.
Which brings us to the manager.
Don Mattingly didn't lose his job with his performance.
He inherited a 9-19 team after Rob Thomson's firing and went 79-55. The Phillies reached the postseason because Mattingly helped rescue a season that appeared finished before May.
And yet the Phillies reportedly are preparing to move on from him. Alex Cora is again looming over the job.
That isn't some new October development.
Dombrowski tried to hire Cora in April before Thomson had even been fired. He acknowledged that if Cora had accepted, he was prepared to make the managerial change. Cora declined because he wanted to spend the season with his family.
That makes the managerial decision fascinating now.
If Dombrowski hires Cora, the Phillies MUST NOT sell this as another attempt to find a different voice for the same clubhouse.
The next manager has to manage the transition.
He needs authority to move veterans down the order. To play younger players through mistakes. To prioritize defense and athleticism. To rethink roles that once seemed permanent.
Otherwise, changing managers accomplishes little.
The same goes for the roster.
The Phillies MUST protect the advantage Middleton identified in March. Sánchez and Luzardo should not become convenient trade chips because the offense needs help. Painter should not be treated as expendable because his rookie season produced a 5.40 ERA. Elite starting pitching is brutally difficult to acquire.
That rotation is not evidence that the old window remains open.
It is the foundation of the next one.
That is the opportunity hidden inside an uncomfortable offseason.
Philadelphia does not need a teardown.
But it does need something harder than another run-it-back winter disguised by two new relievers and a different left fielder.
It needs a transition conducted while Harper can still hit, Schwarber can still change games and Wheeler can still dominate them.
That is why Middleton's Dombrowski decision matters more than any free-agent signing.
Extend Dombrowski if he is the man to build what comes next.
Hire Cora — or anyone else — if he is the manager for what comes next.
Keep the pitching that can carry what comes next.
But stop making decisions designed primarily to preserve what came before.
The Phillies' championship window did close.
Now comes the harder question.
Can they open another one before the pieces they still have are gone?.
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