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25 Smartest Moves of the Past 25 Years: Yankees extend Derek Jeter

Had the lockout not turned the hot stove into the frozen wasteland of Hoth, the biggest topic of conversation surrounding the Yankees would be the impending free agency of the face of the franchise Aaron Judge, the 2017 Rookie of the Year with three All-Star appearances and two top-six MVP finishes to his name as he enters his final year before free agency.

If this sounds familiar to long-time Yankees fans, well, it should be. Around this time 21 years ago, the Yankees faced a similar conundrum with their starting shortstop and face of the franchise, the 1996 Rookie of the Year with three All-Star appearances and two top-six MVP finishes to his name as he entered his final year before free agency prior to the 2001 season.