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I'm going to have to go with no on this one, because I believe that Mariano Rivera will retire before Jeter. And Mariano wears #42, which is already retired throughout all of baseball.

Jeter will absolutely have #2 retired, and will go down as one of the greatest to ever play the game. Just not before Mariano, somewhat because of retirement date and mostly because of Jackie Robinson.
I have to agree with J H that the next number retired by the Yankees would be Mariano's 42 even if the number was not already retired throughout baseball in honor of J. Robinson. I would guess he is the last active player still wearing number 42 who was grandfathered since he already had the number when Baseball decided to retire it across the board.

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