#sam your organizational powers are as always admirable beyond belief

[actuallylorelaigilmore]

I too am in a TWW rewatch, because well I enjoy torturing myself by watching competent articulate political types. (That and the great tv) I'm really struggling with Will. He seems like such an creep the further it goes on yet all the female characters seem to like him. I feel like I'm missing something. Do you have any views on him?

I have views on everything!! :D Seriously though, nobody’s ever asked me about Will so what a great chance for an essay. (This got REALLY long, fair warning.)

First, a disclaimer. I’ve never been very active on Twitter, but when I started using it, I mostly followed TWW actors. I occasionally tweeted at them, and I never expected responses, because they were amazing actors from this show I revered, and I was a random fangirl on social media. But two of them did, and were SO nice, and it shocked me so much back in the day to realize how kind and down-to-earth TWW cast is, when I had just seen the series and hadn’t yet found tumblr or watched interviews. It really made an impression on me. Richard Schiff called me ‘very sweet’ and won my heart forever, and Joshua Malina was also totally friendly and nice, so much so that I felt bad for never really liking his character much.

That’s right, I too used to think Will was obnoxious. But once I realized the actor was kinda awesome, I reconsidered his character and gave him a chance. So I’m glad you asked me, as I’ve been on both sides with Will and really love him now.

IMO, Will Bailey came in not just as a replacement for Sam, but also as a character with very different values, who was meant to contrast with our heroes at a crucial time.

Mid-S4, when Will is first introduced, we meet him as a skilled, idealistic writer who’s also got strong organizational and leadership skills. That’s different from any of our faves, since both Sam and Toby are talented wordsmiths, and both are idealistic in their own ways, but they’re also both oriented towards behind-the-scenes work. Toby is very team-focused and loyal but he would like it if everyone would leave him alone and let him do what he’s good at–messaging and writing and trying to nudge the people around him onto the path he thinks is best. When CJ is promoted above him to become COS, he cares even less about the professional snub than Josh does, because it’s not something he wanted.

And while Sam has political aspirations, he never really shows leadership qualities. He’s an excellent second to Toby and even for Josh when needed, but he’s also shown to be the least canny and experienced of them all, and you could argue that being in front of the camera as a candidate for office doesn’t always equal being a leader, if your staff is really running the show for you, which is what Sam’s campaign looks like. Everyone around him coordinates the details and runs things to leave him space to just be The Guy. But Will Bailey is both the guy running the show behind the scenes AND the guy who can get on camera and speak about the politics and ideals of his campaign because his family and professional background made him much more well-rounded. Heck, he’s even in the armed forces on top of all that! He’s portrayed as good at all the things he does.

Now, what’s interesting to me is that Will, as he’s first introduced, is much more confident and idealistic than he is later on. Early Will goes through a serious transformation, from Toby’s new second to an independent operator who lacks the loyalty the others have to a man more than to a party. To some extent, Will’s rebellious, ‘you need me more than I need you’ attitude was there from the moment Sam showed up to his winning campaign, but I think that who Aaron Sorkin (who had worked with the actor a lot before) conceived him as changed after Sorkin left. The showrunners for S5-7 saw an opportunity in his character’s feisty campaign background and turned him into someone with even less personal loyalty and more detached pragmatism.

The fact is, that’s not what Sorkin-era TWW is about. One of the reasons the later seasons are so different is their clear-eyed look at campaign chaos and shifting loyalties and all the small on-the-ground work that we didn’t see with President Bartlet. The earlier seasons are very much about our found family of staffers and the First Family and watching them fight the status quo that constrains them because they won. They always want to do better, and be better, and as much as they acknowledge the reality that you have to win in order to change the world, the show still promises us that it’s the change that actually matters, and it isn’t worth winning if you have to sell your soul to do it.

So if there’s a spectrum along which everyone falls, based on how much they’re willing to ‘go along to get along’ versus making trouble for the sake of their beliefs, Will Bailey is on the exact opposite end from say, Amy Gardner, with our core characters in the middle. I’ve rambled about Amy before, about how her values and priorities are so different from our heroes that she’s an antagonist even as she works with them a lot of the time. Will has the same complicated relationship with the people we’ve been rooting for for years, but for drastically different reasons. Amy is at odds with the West Wing because she’ll do whatever it takes to win the argument and get what she wants, pulling the Democrats to the left whenever possible.

Will, though–especially in S5 and beyond–is at odds with the West Wing even when he’s in the West Wing, because for all his ideals, he has no problem with compromise. He sees nothing wrong with moving to the middle if it helps you win, if it gets you more power. He’s willing to look like an idiot for the White House, he’s willing to go in front of the press core and be beaten up for days if it will help the cause, he doesn’t hesitate to jump to a new campaign that he thinks could win, because winning is how you get the things you want. Probably, being a diplomat’s son has something to do with how accommodating he is, and how able Will is to justify any position, any choice. We’re told he’s very good with words, but he was probably also good at Debate in school, because he can clearly turn any situation around as needed.

Which means that while Will’s instinct is to adjust and Amy’s is to dig her heels in, they share the one quality that makes any TWW character harder to like: they answer only to themselves. Above all else, their ‘constituency of one’ is themselves rather than a specific politician or even the party. Will is a Democrat, but he’ll happily buck the party wisdom in favor of what he thinks will win. And that puts him up against Toby, the President, Josh, etc, at different times because he bases his choices on his own ideals and they’re just different from those of the Bartlet Administration, which spends 8 years fighting to stay progressive and deciding it’s better to go down fighting than do or say things they don’t believe in.

Will is also an interesting foil for Donna after she leaves the White House, and not just because they become coworkers and good friends. Along with the fact that she left Josh and struck out on her own, most of her post-Sorkin conflict with Josh is actually based on WHO she went to work for and how differently she and Josh see that decision/what it says about her and her time working under Josh. By going to work for Russell, Donna shows that she’s less concerned with finding the perfect underdog candidate and more interested in a future that keeps up Democratic progress after President Bartlet leaves office. She is never dedicated to Russell as a man, and over time becomes visibly concerned with his flaws as a man and a candidate. But tellingly, Will isn’t any more personally loyal to Russell than Donna is–and he’s the one running the man’s whole campaign!

It says a lot about Will that for all the moments when Russell shows himself to be less than honorable, Will clearly disagrees with his actions…but he stays. Because Russell was never why he left the Bartlet Administration, or why he took on the new campaign. He took it on because he’s good at winning campaigns, and in Russell he saw someone who could win, and he may have even admired the antagonistic streak that came out once Russell became VP. Russell also had no interest in the ‘cult of Bartlet’ and quickly proved that he wouldn’t even have the level of respect that Hoynes had for Josiah Bartlet as a man. Most of the characters on TWW consider that strike one against Russell and a major character flaw, but Will doesn’t. He respects the President and the office but he didn’t know Jed before the MS reveal, he sees him from more of a removed distance, and his White House job is a JOB to him more than a calling.

Again, some of this was less true during the Sorkin era. The Will Bailey who lost the ability to speak when he was officially offered Sam’s position is much more in awe of the gravity of it all, and it’s hard to see that guy jumping ship to support a moderate candidate that nobody in the White House even likes. But the hints of who he ends up as were there from the beginning, the way he tells off Sam and Toby even before he works with them–he’s always an outsider.

So the outsider factor, that makes it harder to like Will or any TWW character that doesn’t automatically get along with the others. Ainsley Hayes may be ‘the enemy’ as a Republican, but she is amiable and smoothly tries to change minds–and when she isn’t able to, she opts to live and let live. Will is harsher, more combative at times, and I don’t know if it’s just me, but that makes me feel defensive and protective towards the staffers he’s arguing with. After all, I adore them and I barely know him, how dare he?

But of course, his actions and his beliefs make perfect sense from HIS perspective. He’s had a successful career, and being a part of the Administration was never a goal of his, so he doesn’t need to go out of his way to defer to their judgement or stay quiet in the face of their superior wisdom. He was raised to know how to work people and get his way, but he was also raised with incredible privilege and confidence and if he was banished from TWW inner circle it wouldn’t be much of a loss for him. Being an outsider isn’t a problem for him, he spent his life that way as a diplomat’s son, so he never feels the need to conform the way he would have to in order to really become a part of the gang.

Honestly, the only reason he ever gels as a part of the group is because Josh leaves and Toby is fired and they need Will to speak for the White House–finally he’s the ultimate insider, he’s the Bartlet mouthpiece, and the only original senior staffer left is CJ, so once Will and Kate bond they’re the center of the staff that’s left, and he has somebody on his side. (And once he’s off the campaign trail, the show goes back to highlighting his neurotic and geeky side, because he can’t be the ‘win at all costs’ guy anymore and needed a new focus.)

So here’s why I think it can be hard to like Will: he often seems like an entitled, immune-to-criticism, antagonistic opportunist. At his worst he seems to think the means justify the ends, despite his progressive beliefs in general, and that means he’s the guy who could get almost anybody elected–which is great when it’s S3 and Bruno Gianelli is on Bartlet’s side, but less so when Russell seems like not much of an improvement on Hoynes in terms of decency and intelligence and Will has the skills to actually make that guy President.

BUT, (and I can’t guarantee this will help you but I think it’s important because Will does exist as a complex, multidimensional character, and that’s a good thing even though it means he has flaws) at his best he is an adorable dork who wants to make the world better, will take jobs because he believes they need doing even if they’re not his own personal dream, is willing to put himself in danger to save and protect others, and is not just talented but also very knowledgeable about the same kind of geeky Constitutional and political history that Jed Bartlet is.

What I’m trying to say is that Will, as much as anyone on TWW, is the product of his good and bad qualities, and both sides of that equation come from his core traits. His ability to ignore others’ criticism because he’s secure in who he is can be annoying when it’s Toby or Josh trying to talk sense into him, but it also means he survives hazing with friendly ease and stands up for the White House’s positions like a pro. He cares more about winning than fighting the narrowest version of the good fight, but he’s not wrong that winning is better for progressive goals than losing for the sake of ideological purity (hi 2016, I have not missed you). He isn’t loyal to the Bartlet Adminstration above all else–but if everyone were, then the President would be a dictator. Intra-party fighting can weaken a party but it also allows for diversity rather than a cult mentality.

So, here’s what it comes down to. Will isn’t Sam, and that means Toby could never really like or trust him, even if he had become more loyal. Will is a political relativist, which means Josh was never going to agree with his choices, as Josh has always put people first and hates having to compromise. Will is a privileged white guy (played by a Jewish actor, but never canonically established as Jewish) so CJ tolerates him but doesn’t genuinely like him for some time, because that’s just how she rolls. Leo leaves Will under Toby’s purview, and Jed has even less direct interaction with him. He spends a lot of his time battling a group of young female interns we never see again (tbh I can’t stand those scenes and if that’s where you get your creep factor, I get it). Given how disconnected he often is from the central cast, is it any wonder he’s mostly underappreciated and ignored by fans as well?

As for why the female characters on the show don’t seem bothered by him, even when you are, I think there’s a couple of possible explanations. First of all, TWW is a show that doesn’t show us that much–we have to assume that all of these characters, who practically live at work, spend a TON of time together offscreen, just by the nature of their jobs. If most of that time is similar to Will’s comedic scenes, where he’s a giant nerd with bikes in his office whose response to stress is the fetal position, then presumably his coworkers see his flawed human side, in an endearing rather than annoying way.

And secondly, we as viewers don’t have that perspective. We don’t even have the benefit of being these characters living in the early ‘00s, when it was a given that the government would be full of overconfident oblivious men and that’s just what women were expected to handle with poise and sweetness. Clearly things haven’t changed much over the years when it comes to White House staff and a backdrop of misogyny at work, but for a lot of us as viewers the world has progressed.

So Donna gets along with Will as her boss who can be kind of dense or morally ambivalent sometimes, but she’s also spent almost a decade dealing with the most powerful men in America. As an assistant, for most of that time. To her, even Will’s worst moments are barely a blip in the grand scheme of things. And CJ is totally unimpressed by Will’s smarts and talent because she works with the smartest and most talented men she’s ever known, but he serves a purpose and doesn’t get in her way, so she has no problem with him. Kate rose to power through the ranks of military men and has definitely seen, and probably injured, worse guys than Will Bailey. All the women of TWW have spent their careers dealing with men of varying character. I mean, even compared to some of Sam’s comments, Will must seem downright harmless.

TL;DR Can Will Bailey be a patronizing know-it-all who puts his own interests before party and found family? Absolutely. Is he a bad guy? Not at all. He’s just a different kind of good guy than those The West Wing conditioned us to admire and root for.