Yankees Facing Pressure After Blue Jays, Red Sox Early Offseason Moves

After reaching the World Series in 2024, the New York Yankees’ season came to a disappointing end in the ALDS, with the Toronto Blue Jays defeating the Bronx Bombers in five relatively lopsided games.

Coming out of the disappointing playoff loss, what the Yankees needed to do to improve the roster was clear: add more pitching depth, find another bat or two, outside of re-signing Cody Bellinger, and determine the future of some of New York’s underwhelming young pieces, such as Anthony Volpe.

What has Brian Cashman and the Yankees done to answer these unknowns: nothing

The pressure is mounting for New York to make some major moves over the winter months, especially with what’s going on around the division, and what the team that eliminated the Yankees has already done to improve its roster for next year.

The Blue Jays went on to the World Series and even had the Los Angeles Dodgers on the ropes before falling to the eventual back-to-back champions in seven games.

Toronto identified its shortcomings and went out to sign Dylan Cease to a seven-year contract to address its pitching needs.

The Boston Red Sox were in a similar position as the Blue Jays after barely missing the postseason. They went out and traded for Sonny Gray from the St. Louis Cardinals, and have now reportedly shifted their focus to adding to their lineup.

So far this offseason, the Yankees have re-signed LHP Ryan Yarbrough to a major league contract and signed RHP Michael Arias and RHP Yerry Rodriguez to minor league deals.

Sure, there could be some nice depth pieces for the Yankees next season, but they don’t raise New York’s ceiling to becoming World Series contenders.

Yes, there’s still a ton of time in the offseason for the Yankees to make moves. In fact, we rarely see blockbuster trades or top free agents sign before Thanksgiving.

Yet, the Blue Jays and Red Sox have sent a message to New York and the rest of MLB that they plan to be active this offseason in building a World Series-caliber roster for the 2026 season.

With the Boston and Toronto already making major moves, it certainly puts pressure on Cashman and the Yankees to keep pace and ensure they remain a playoff contender, giving them a chance to win the AL East next year, or they could risk falling into mediocrity in their own division.