The New York Yankees face another offseason of uncertainty after yet another early postseason departure, forcing general manager Brian Cashman to weigh creative roster adjustments rather than relying on a thin free-agent market.
New York is no longer the free-spending powerhouse of years past, and while the roster lacks obvious major holes, the recent pattern under Aaron Judge has failed to produce sustained October success.
Trading from a position of strength in the starting rotation offers one logical path forward.
Matthew Schmidt of Yankees Roundtable feels a trade is “inevitable,” specifically involving one of the club’s back-end starters, Will Warren or Ryan Weathers.
The Yankees currently boast six capable arms in Cam Schlittler, Gerrit Cole, Max Fried, Carlos Rodón, Warren, and Weathers, with prospects such as Elmer Rodriguez and Carlos Lagrange also advancing.
Retaining both Warren and Weathers provides valuable insurance against the injuries that plagued the staff this season, yet carrying both may not be necessary once the front four are healthy.
Schmidt’s view underscores how the surplus creates a natural opportunity to address other needs through a deal.
Warren delivered a 3.92 ERA across 29 starts in 2026. His 1.365 WHIP and 9.2 hits per nine innings were elevated, but those figures remain acceptable for a fifth starter.
Weathers, by contrast, posted a 3.60 ERA in 25 starts before an elbow flexor strain sidelined him for the final month.
He showed flashes of dominance and struck out batters at a 9.4 rate per nine innings, though consistency remained an issue throughout the year.
Either pitcher could command a useful return, particularly if the Yankees are willing to sell high on Weathers given his recent injury history.
New York could also envision Weathers shifting to the bullpen next season, especially if left-handers Ryan Yarbrough and Tim Hill depart in free agency alongside right-handers David Bednar and Paul Blackburn.
In that scenario, the organization might view the lefty as a valuable late-inning option rather than a pure trade chip.
Even so, the presence of multiple reliable rotation options means the Yankees can afford to move one of the two without seriously compromising depth.
A deal for either Warren or Weathers therefore appears likely this winter as Cashman seeks incremental improvements that can finally alter the franchise’s postseason trajectory.
