By: Jim Williams
Senior Columnist, Capital Sports Network
The Bronx Blues: Another Familiar Ending
The New York Yankees’ season was always going to end this way. That’s because every Yankees season of this era ends this way—spiritually speaking. Since Aaron Boone took over for Joe Girardi in December 2017, he’s done two things with remarkable consistency: win during the regular season and lose during the playoffs. Why would 2025 be any different?
This year’s heartbreak came courtesy of the Toronto Blue Jays, who eliminated the Yankees in four games in the American League Division Series. Wednesday’s 5–2 loss in Game 4 sent the Bombers packing, while Toronto punched its ticket to the ALCS. For Yankees fans, it was déjà vu all over again.
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Free Agents Departing, Holes Emerging
With the offseason now underway, the Yankees face a roster in flux. Several key contributors are heading toward free agency, including outfielders Cody Bellinger and Trent Grisham, both of whom provided flashes of brilliance but lacked consistency. Carlos Rodón, once expected to anchor the rotation, may also be on the move after a disappointing postseason.
The infield remains a question mark. Anthony Volpe struggled at the plate and in the field during the playoffs, raising doubts about his long-term fit at shortstop. The Yankees could look to upgrade there, especially if a star like Bo Bichette becomes available via trade.
Big Bats and Bold Moves?
If the Yankees want to shake up their lineup, they might not have to look far. Pete Alonso, the Mets’ slugger, is rumored to be on the Yankees’ radar. His power bat could provide much-needed protection for Aaron Judge, who continues to carry the offense but can’t do it alone.
On the pitching front, Dylan Cease is a name to watch. The hard-throwing right-hander from the White Sox could bring stability to a rotation that faltered in October. With Gerrit Cole still dominant, pairing him with Cease could give the Yankees a formidable one-two punch.
The Steinbrenner Way—Sort Of
Owner Hal Steinbrenner and GM Brian Cashman are committed to improving the team, but Hal is not his father George. There will be spending, yes—but not the kind of blank-check aggression that defined the Yankees of the early 2000s. The front office will be strategic, not impulsive.
As the calendar turns toward 2026, the big question looms: Who will show up in Tampa for spring training wearing pinstripes? The Yankees have talent, money, and motivation. What they need now is direction—and a postseason breakthrough that’s long overdue
