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Yankees Already Predicted to Swing Huge Trade for 3-Time All-Star

New York Yankees
Oct 3, 2026; St. Petersburg, Florida, USA; New York Yankees manager Aaron Boone calls the bullpen in the eighth inning against the Tampa Bay Rays in game one of the ALDS for the 2026 MLB Playoffs at Tropicana Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images

The New York Yankees have barely cleared the clubhouse after another early October exit, and one of the first names attached to their winter is already William Contreras.

Bleacher Report’s early look at the 2027 roster does not treat the Milwaukee catcher as a rumor on the margins.

It writes him into the Opening Day lineup, with Austin Wells sliding to the bench, as the clearest position-player change Brian Cashman’s group is projected to make after the American League Division Series loss to the Tampa Bay Rays.

Kerry Miller, in that Oct. 7 offseason guide, frames the idea around how Milwaukee has operated before.

He points to Freddy Peralta this past winter, Devin Williams the year before that, and Corbin Burnes the offseason before that as evidence that the Brewers will move a star ahead of a final season of team control, and that they have kept improving after those deals.

Contreras carries a $14.5 million club option for 2027. Miller’s case is that Milwaukee could use another starter or two in a rotation that thins quickly past Jacob Misiorowski and Logan Henderson, and that New York is unusually well stocked in exactly that area.

The catching hole is not subtle. Wells steadied himself after a brutal first half and won the third-most automated ball-strike challenges among catchers, but Yankees backstops still hit .196 as a group. New York did not address the position at the deadline, even when the numbers were worse.

A right-handed bat who can take the majority of the starts, or at least split the job, is one of the few everyday upgrades that would change the lineup without waiting on a prospect.

What makes the prediction more than a wish list is the surplus on the mound. Cam Schlittler, Max Fried, Gerrit Cole and Carlos Rodón are all signed through at least 2028.

Behind them sits a crowd for the fifth spot: Will Warren, Ryan Weathers, Luis Gil, Clarke Schmidt and Elmer Rodríguez, with only Schmidt short of two more years of control.

Miller’s view is that New York will not hoard that depth the way a team with a thinner rotation might. At least one of those arms is the currency for an upgrade elsewhere, and catcher is the spot where an upgrade would show up every night.

None of this is a completed trade. Contreras is still in Milwaukee’s postseason, the option has not been decided, and a package built around a controllable starter would have to satisfy a front office that has been disciplined about when it sells. The projection is still pointed.

If the Yankees follow the path Miller sketches, the longest World Series drought in more than a century does not begin with another year of hoping the catching situation sorts itself out.

It begins with Contreras behind the plate and Wells in reserve.

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