​Yankees offseason outlook: What’s next for New York, Aaron Judge after another disappointing playoff loss originally appeared on The Sporting News.
Add The Sporting News as a Preferred Source by clicking here.Once again, the New York Yankees enter the offseason following a disappointing playoff exit, as they lost to the Tampa Bay Rays in the ALDS.While the team didn’t have Aaron Judge at its disposal in the playoffs, there was still the expectation that New York could make a deep playoff run. Instead, the Yankees head back to the drawing board to try and figure out how to best build around their star players.Aaron Judge will, of course, be back, hoping for a healthier season after he had an injury-riddled 2026 season. Judge is getting older, though, and his superstar abilities will only be on display for so much longer before New York has to reckon with a diminished version.This offseason could be strange, with the lockout looming, but the Yankees are in good shape regarding most of their team for 2027. However, fans will demand major changes with another year going by without a World Series title, even if the market for players isn’t as robust as in years past.Here’s a breakdown of how the Yankees can approach this crucial offseason.Yankees free agents 2027OF Trent Grisham2B Jazz Chisholm Jr.RP David BednarRP Paul Blackburn1B Paul GoldschmidtIF Amed Rosario The Yankees have most of their roster set to return in 2027, with only a few notable free agents hitting the market. Trent Grisham and Jazz Chisholm Jr. are the biggest names, but New York has possible in-house replacements for them in Spencer Jones and Anthony Volpe making it so the team can move forward without them.The area that will need total attention for the Yankees in the offseason is the bullpen. David Bednar was excellent for the team since the 2025 trade deadline, making it so he should be New York’s top free agency priority. Paul Blackburn also hits free agency after a career year along with other Yankees middle relievers, and New York will have either bring them back or replace them next year.Of note, the Yankees are set to bring back their entire rotation, which was one of the best in baseball in 2026. The six-man group led by Cam Schlittler is as deep as any team’s rotation, with the lone free agent being Clarke Schmidt coming off of Tommy John surgery. MORE: Yankees playoff history with Aaron JudgeYankees offseason targetsEntering the offseason, the biggest area of offensive improvement the Yankees could make is in the infield with Jazz Chisholm hitting free agency and Ryan McMahon on the final year of his deal. New York should have Ben Rice, Luis Garcia Jr. and George Lombard Jr. all play big roles, but they could use some help.The free agent market, however, is thin this year, especially on the infield. The best infield free agent would be Bo Bichette if he opts out of his deal, but he is more likely to return to the New York Mets for another season. Other