The New York Yankees passed on the chance to sign Yoshinobu Yamamoto two years now, and they are still paying the price for it.

The Yankees are in the early stages of offseason planning and we have little idea of what their roster will look like on 2026 Opening Day, let alone when pitchers and catchers report in mid-February. But that doesn’t mean we can’t partake in a little speculation about one player in particuar.

Former Yankees closer Aroldis Chapman says he’d “rather retire” than return to New York, citing disrespect from team executives.

The Yankees have not won a World Series since 2009, and the team may feel pressure. That could mean the team will look to make a splash this offseason. Kyle Tucker is the best available free agent, and his next contract could reach north of $400 million. However, there are concerns about whether he deserves that.

New York has to clear 40-man spots and salary before Nov. 21. Several relievers could be cut so the Yankees can manage payroll and survive 2026 without Gerrit Cole on Opening Day.

The Yankees are overhauling their coaching staff and brought back a familiar face to assist pitching coach Matt Blake. Desi Druschel, who was on staff before going to the Mets in 2024, was rehired by the Yankees.

The New York Yankees could be looking for arms in the bullpen this offseason and could target one from the New York Mets.

The New York Yankees’ season ended with that familiar sting of unfinished business. They powered past the Boston Red Sox […]