What Cashman Said at the Winter Meetings — And What It Means for the Yankees

In today’s video, I break down what Brian Cashman said at the Winter Meetings and what his comments actually mean for the New York Yankees moving forward. Cashman touched on everything from the offseason approach to roster construction, internal evaluations, and how the organization is thinking heading into 2026.

As a former MLB player who lived through front office conversations and team decision-making firsthand, I wanted to give you the player perspective on what Cashman’s answers really reveal — the good, the concerning, and the things Yankees fans should pay attention to.

If you’ve been following every offseason rumor or you’re trying to understand the direction of the team, this breakdown will give you context you won’t get anywhere else.

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