21. Jorge Posada, 2002: Five Years, $51 Million
Jorge Posada tested the waters of free agency after the 2001 season, but re-signed with the Yankees by early February at a massive cost. See how tough it was to keep this core together?!
Posada further blossomed into stardom on this contract, finishing third in the MVP race in 2003 by drilling 30 homers, slugging .518, getting on base at a .405 clip, and dinking a Pedro Martinez pitch into shallow center field to tie Game 7 of the 2003 ALCS (ok, fine, MVP voters didn't actually consider this, but it was cool as hell).
Posada will also appear on this list again later on.