4. Doug Drabek, Logan Easley and Brian Fisher for Pat Clements, Cecilio Guante and Rick Rhoden, 1987
That same 1987 season that saw Tewksbury traded also saw a future Cy Young award-winning pitcher shipped out. At the center of the trade was Rick Rhoden. Rhoden was brought in the help the Yankees to become a contender.
To his credit, Rhoden played the part. Coming off a season with the Pittsburgh Pirates that saw him win 15 games and finish fifth in the Cy Young voting, Rhoden continued his success with the Yankees. The other two players acquired served as solid options in the bullpen. On the surface, this trade looked like a win for the Yankees — at least, it did in 1987.
Little did the Yankees know that pitcher Doug Drabek would embark on a run of six straight seasons of double-digit wins. In fact, he would have double-digit wins in nine of his next 12 seasons. He would win the Cy Young award in 1990, also placing eighth in the MVP voting. He would finish fifth and fourth in the Cy Young voting in 1992 and 1994, respectively.
Drabek made the playoffs three consecutive years with the Pittsburgh Pirates from 1990-1992. He pitched well in the playoffs, posting a 2.05 ERA, but he was the pitcher of record for three losses to the Atlanta Braves in 1992. This speaks more to the pitching staff of the Braves at that time than Drabek.
But Drabek was only traded by the Yankees once. The next player was not lucky enough to have that distinction. In fact, he was traded to the same opposing team twice in the same season.