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Joshua Malina as Will Bailey, Deputy Communications Director
NBC Photo by Chris Haston
- "Hired to help Toby with the Inauguration Speech" - Later Deputy Communications Director (taking over Sam's old job after Sam went off to California to run for Congress).
- Later he becomes the Vice President's Chief of Staff and Campaign Manager for Russell's run for the Presidency.
- Then after Toby is fired, he is "dragooned" by C.J. to take over the job ov Communications Director
- Played By: Joshua Malina
- Father: General Tom Bailey - NATO Supreme Commander of Allied Forces (he was once referred to by President Bartlet as "the very model of a modern Major General" [#414]).
- Mother: no information
- Siblings: We know about a step-sister, Elsie Snuffin.
- Education: Eton valedictorian. And Cambridge: "I was President of Cambridge Union on a Marshall Scholarship" [Artic Radar] (we were reminded of this information by Ian Preston, who wrote, "Will mentions to Toby that he was the president of Cambridge Union which, as well as being Cambridge University's student union also features a very highly respected debating society. It's not clear whether he attended Cambridge at undergrad or graduate, but given that the Marshall scholarship is only rarely awarded to undergraduates it's more likely that he was there as a grad student.")
- Religion: unknown
- Background: Raised in Brussels
- Work History: Campaign manager whose candidate died during the campaign and who still won the election. Will also ghosted an extraordinary speech for the Governor of California
- Currently an officer in the Air Force Reserves:
"Will, why are you dressed like an officer in the Air Force?" the Presidents asks from the midst of his co-workers poker game.
"I'm an officer in the Air Force."
"You're a Reservist?... I didn't know that. Did you know that?" The Presidents seems to direct his question specifically to C.J.
"He's First Leutenant Will."
"I had no idea. What do you do?"
"I work with the JAG Corps."
"...Where are you stationed?"
"Since I moved here, I'm stationed at the Air Force Legal Services Agency at Bolling Air Force Base...."
- Romantic Interests: He seems to be developing something with Kate Harper (April Whiteside reminded us to include this info).
- What He Says About Himself:
- "Personally I'd have no problem using force on Congress. but that's not my call." [#414]
- "I like to think I have a certain flair." [#414]
- Conversations With Will:
- "Willy," Elsie says.
"Don't call me that!" [#417]
- "Can I ask you something?" --- Charlie to Will.
"Do you have a girlfriend right now?"
"When was the last time you had one?"
"About nine months ago."
"And how long did it last?"
"In my own defense, she was psycho."
"So why are you giving me relationship help?"
"'Cause I'm the only one in this conversation who didn't get a 'Dear John" email from his ex-girlfriend's boyfriend."
"God, that's really true, isn't it."
- "It's going to be fine." Charlie tells Will about the landing gear problems.
"What do you mean?"
"I know you're afraid of flying."
"I can tell." Then when C.J. joins them, Charlie tells her, "...Will's afraid of flying."
"It's okay. You're afraid of flying."
"I'm not. I'm not afraid of flying. I experience flying."
"Why'd you sign up for the Air Force Reserve?"
"Well, I did it for a lot of reasons and one of them was for the romance of flight but I got over that. I never thought that would happen. But these guys practice hard landings all the time. This isn't a big deal." 
- "You have a certain quality about you that says that even though you're a capitalist, you've been schooled in Eastern philosophies," Toby tells Will.
"Well schooled. You want me to locate your chakra? I'm a lawyer."
"Good, 'cause they're never annoying." (this dialogue came from Joshua Rasiel)
- What Others Say About Him:
- "I can confirm that he is thinking and familiarizing himself simultaneously." --- Will's step sister Elsie Snuffin to Toby. [#414]
- "He's a very sweet hard-ass." --- Will's step sister Elsie Snuffin telling Will what she had told the interns about him. [#417]
- Joshua Malina also starred in "Sports Night", also created, written, and produced by Aaron Sorkin.
- His approach to other things:
- "There's this thing called the Constitution. It's a nagging little document, I'll grant you..." [#507]
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