Will Bailey

William Bailey is a fictional character played by Joshua Malina on the television serial drama The West Wing. He holds a series of posts in the White House Office of Communications, the Office of the Vice President, and as a backbencher Congressman (as seen in Season 7, Episode 1). The character was introduced after Rob Lowe, who played Sam Seaborn, left the show.
Character biography
Will grew up in Belgium, where his father, General Thomas Bailey, served as the NATO Supreme Allied Commander, and in whose ideological footsteps he seems to follow, while making a name for himself with quiet resolve. Will is an Air Force reservist, a commitment that President Josiah Bartlet applauds, serving in the . In the episode "Guns Not Butter," Will says he is an Eton valedictorian. (This is a factual error, as the title does not exist in Britain). He may have attended Carnegie Mellon University, as he wore a Carnegie Mellon shirt while jogging at Camp David. He attended the University of Cambridge, England, as he said he was "President of Cambridge Union Society" and on a Marshall Scholarship. He also owns a mug featuring the coats of arms of Cambridge colleges and a framed diploma with the University's coat of arms hangs on his office wall in Season Seven. Will entered politics as a campaign speechwriter on two congressional races: the 2002 Horton Wilde campaign (see below), and a 1994 congressional race in Oregon's 4th congressional district, in which Will's candidate, Chulo (D), lost by fifteen points to Congressman John Heffinger (R).
Will is originally introduced as the manager of the Horton Wilde campaign to represent California's 47th congressional district, and he gains recognition for forcing a run-off election despite Wilde's death. Sam Seaborn arrives to tell him to shut down the "embarrassing campaign," but Will defies him and Sam is won over by his efforts despite the seat's traditional status as safely Republican in the conservative Orange County. Sam later runs in Wilde's place in a special election while recommending that Will to replace him as Deputy White House Communications Director with a note to Toby Ziegler that reads: "Toby — He's one of us." Will ghostwrites an acclaimed speech that California Governor Gabriel Tillman gives at the Stanford Club, which is what brings his writing skills to Sam's attention, although Toby is more critical of the speech. Toby, after first meeting him, characterizes Will as "deeply schooled in Eastern philosophy," but is won over by a five-hundred-word "test essay" about America's future foreign policy needs.
When Will moves into Sam's old office for a three-week temporary contract to help with second inaugural address, he endures hazing by White House staff that includes "Seaborn For Congress" posters plastered on the walls and bicycles stored in his office. CJ Cregg regularly put olives in his pockets and at one point places a goat in his office. Will eventually wins everyone over, and Bartlet eventually appoints him to replace Sam as Deputy White House Communications Director, although all the staff writers quit afterwards in protest and he has to turn for help from to a group of young female interns and his step-sister .
Will leaves President Bartlet's staff soon after the appointment of Representative Bob Russell (D-CO) as Vice President of the United States, when he accepts Russell's offer to become his chief of staff. The main reasons for his move to Russell's office are Toby's gruff attitude as his direct superior and a belief that Toby's tendency to personally take charge of challenges for the Communications Office will result in zero potential for Will's advancement. Bob Russell's offer, in contrast, comes with the explicit challenge to prepare the Vice President for a presidential campaign in 2006. Despite his initial distaste for Russell, Will agrees to run the Russell presidential campaign because, as a die-hard Democrat, Will sees the V.P. as the presumptive nominee in the general election, and wants to get an early start grooming Russell for the Oval Office. However, in the episode "365 Days," Will secretly admits to Leo McGarry that he has doubts about his choice of candidate, and has been backing him so vigorously only because he has been accepting on faith that Bartlet and McGarry must have had noble reasons for selecting Russell as Vice President.
When Leo McGarry is unable to serve as Chief of Staff following his heart attack at Camp David, White House reporter Greg Brock suggests that Will might be appointed as Bartlet's new Chief of Staff. This is due to a rare meeting between Bartlet and Will about NATO peacekeeping, Will's experience with the military, and his proven ability to "manage up", qualities that perhaps make him a better choice for the role than Josh or Toby. However, C.J. Cregg is chosen for the job and Will remains Chief of Staff and Campaign Manager for Vice President Russell.
When Russell loses the Democratic nomination to U.S. Rep. Matt Santos (D-TX), Bailey remains on Russell's staff until White House Chief of Staff C.J. Cregg "dragoons" him on very short notice to become White House Communications Director after the firing of Toby Ziegler for his role in the military space shuttle leak. Since Toby has also been serving as de facto White House Press Secretary, Will also inherits that role.
In the seventh season, Will dates Deputy National Security Advisor Kate Harper, with whom he had clashed over Israeli-Palestinian peacemaking. The affair begins when she asks him to Ellie Bartlet's wedding, but their first real date is in "Running Mates". Their relationship is touched on again in "The Cold", where they seem awkward together.
On Election Day, with the Bartlet Administration soon to be replaced, Will reveals that he is considering a return to election campaigning, citing a job offer to run a Californian mayoral contest. This would mean leaving Washington, D.C. and cause problems for his relationship with Kate. In the penultimate episode Institutional Memory, Will considers taking a job as the Chief Executive of the Democratic Congressional Campaign Committee, but becomes preoccupied with the task of finding a candidate to challenge incumbent Republican Congressman John Heffinger in the in 2008. Kate realizes that Will would make the perfect candidate, and insists that he move to Oregon in time to gain residency status and run for the seat, a move also encouraged by Bartlet.
By the time of the dedication of the Bartlet Presidential Library in New Hampshire three years later, Will is a Congressman representing the and sits on the powerful Ways and Means Committee. He describes himself as a "back bencher who may have a shot at chairman in thirty-two years." It is not revealed what happens in his relationship with Kate.
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 in Sorkin's TV series Studio 60 on the Sunset Strip and other subsequent Sorkin productions). 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 is an example of a theme that runs throughout the series, i.e., the contrast between 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 has the better chance of 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."
Will's career trajectory bears a number of similarities to that of Eli Attie, a writer and producer of the series and one of the architects of the character's storyline. Like Bailey, Attie had been a Presidential speechwriter and communications aide who left President Bill Clinton's staff to take a higher-ranking job with Vice President and presumptive Democratic nominee Al Gore.

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