Brian Cashman’s extensive trade deadline history provides bread crumbs for Yankees’ potential strategy

hardball Joel Sherman Brian Cashman’s extensive trade deadline history provides bread crumbs for Yankees’ potential strategy By Joel Sherman Published July 18, 2026, 9:55 a.m. ET Brian Cashman has holes to fill at this year's trade deadline. Corey Sipkin for the NY POST Brian Cashman has completed more than 100 trade deadline deals since becoming the Yankees general manager in 1998. It is hard to come to peace with exactly what defines such a transaction. For example, I would include the early deal in June 2000 for David Justice as a deadline deal and also swaps made through August before the waiver deadline was eliminated after the 2018 season. But my standard would not include the purchase of a contract without a player moving the other way.

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