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.

Since then, he played one season with the Pittsburgh Pirates and another, revitalized season with the Red Sox. In 67 appearances with the Yankees’ division rival, Chapman posted a career-best 1.17 ERA while striking out 85 batters over 61 1/3 innings.

Will the New York Yankees move on from a fan-favorite infielder this offseason? It's worth pondering, says this insider.

The Seattle Mariners were one of the best teams in all of baseball this season, but they fell short of the ultimate goal of the World Series. Seattle made moves

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

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After a swing change propelled him to a breakout season, Rice may deserve a shot at the Yankees’ full-time starting first base job in 2026.

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.