I think the Yankees definitely resign him. Cano is really the only Yankee I can think of that they let walk during their prime years. But maybe they had an insight into issues to come and that's why they made that decision.
Even while Cano was great, Jeter was still on the team. As another poster said, Judge is the biggest thing since Jeter. I can't think of anyone like Judge that the Yankees let get away.
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