High Quality Content by WIKIPEDIA articles! Clifford "Cliff" Calley is a fictional character played by Mark Feuerstein on the television serial drama The West Wing. Appointed Director of Legislative affairs to fill the political planning void after Josh Lyman left the White House to serve as campaign manager for presidential candidate Matt Santos. Realizing Lyman had left a big hole when he left, and that Calley possessed many of the same qualitites as Lyman, Chief of Staff C.J. Cregg dragooned him into taking the White House Director of Legislative Affairs job.