Will Bailey - Character Significance

Character Significance

Will Bailey is portrayed by Joshua Malina, an actor who at that time had appeared in every work (both on stage and on screen) written by West Wing creator Aaron Sorkin (although he did not appear subsequently in Sorkin's TV series Studio 60 on the Sunset Strip). After the series spent much of Will's screen time establishing his struggle to fit in with the rest of Bartlet's staff, his decision to leave the staff in favor of working for Russell again establishes him as an outsider, while his later decision to pour his considerable political acumen into running Russell's presidential campaign frequently puts him at odds with several of the more familiar characters, most notably Josh Lyman, who runs the Santos presidential campaign, and Toby Ziegler, who points out (in the episode "365 Days") that Toby and Will used to make fun of Russell together.

The Josh/Will conflict in particular is an example of a theme that runs throughout the series—namely, the contrast between two different approaches to politics, Idealistic (Josh backs a long-shot candidate because he believes in the candidate's noble character) versus Practical (Will backs a candidate he is unsure of, because he thinks Russell is the best chance of a Democrat winning the race). Placing Will on the side of compromise and practicality contrasts sharply with his earlier idealism, when the character was introduced running a campaign for a deceased Democrat in a traditionally Republican district, and defending his actions as "a campaign of ideas."