West Wing Retrospective: Character Study

David B Morris
16 min readJun 2, 2024

Richard Schiff as Toby Ziegler — How His Eternal Misery Showcased His Political And Emotional Flaws

Richard Schiff at the 2000 Emmys.

Until Game of Thrones came along the all-time record holder for both Emmy nominations and wins for a dramatic series was The West Wing. It came out of the gate early, breaking the record held by Hill Street Blues and ER for most wins by a Drama with nine in its first season, including the first of four consecutive Best Drama Awards. No drama in history has ever won more Best Drama awards; this mark has been equaled in the 21st Century by both Game of Thrones and Mad Men, with the latter also winning them consecutively. It finished its run with 26 over its seven year run.

The vast majority of the Emmys the show won were during the Aaron Sorkin era with the series winning 23 of them during his four years as showrunner. I’ll acknowledge that the last Best Drama the show won in 2003 was undeserved (it should have gone either to Six Feet Under or 24) but I have few problems with most of the rest of the awards, in particular when it came to acting. In hindsight The West Wing was the first series in my viewing experience that I recognize having one of the greatest ensemble casts of its time, not only with all of the named actors but the vast majority of the recurring and guest actors that the show employed over its seven year run. The West Wing is one of the few shows in history where every regular who was on the show for the majority of its run received at least one Emmy nomination for acting and with the exception of Rob Lowe and Dule Hill (both of whom should have received far more) every actor during the Sorkin years was nominated at least three times. (Janel Moloney, the most undervalued cast member, only received two.)

And the four actors who were the heart of not only the show but the Bartlet White House during the run of the series: Bradley Whitford, Richard Schiff, John Spencer and Allison Janney received the most recognition from the Emmys during the Sorkin era: Schiff and Whitford received three Emmy nominations for Supporting Actor in a Drama, while Spencer and Janney were nominated every year during that period. Janney was nominated for Supporting Actress the first two years of the shows run and Best Actress the next. All four won Emmys; Schiff in 2000, Whitford in 2001, Spencer in 2002, and Janney 2000,2001 and 2002. (She would win again in 2004 and honestly I consider that one the Emmys got wrong.)

Now I’m not saying the rest of the cast wasn’t brilliant in everything they did during this period: they overwhelmingly were. And indeed not all of the actors in the cast deserved more recognition than they got from the Emmys over the years. Martin Sheen would joke that he was the only actor from the cast who didn’t win an Emmy and while that was unjust he also had the misfortune of having all his nominations come at the time when the age of the cable antihero was becoming prodigious. He lost to James Gandolfini for The Sopranos three times; Michael Chiklis for The Shield, Kiefer Sutherland for 24 and James Spader for his work as Alan Shore, first on the final season of The Practice, then on the first season of Boston Legal. Considering that he was also perennially competing against some combination of these actors as well as both Michael C. Hall and Peter Krause from Six Feet Under and Ian MacShane from Deadwood, it’s hard to imagine a scenario where he could have eked out a victory.

It’s actually just as impressive so many of the actors from The West Wing managed to win in this era: all of them were competing against supporting cast members from both The Sopranos and Six Feet Under during much of this period. They were helped in part by the fact that during the first three years of their run the Emmys was locked into its traditional network views and old habits. But it’s also due to the fact that all of their characters on the show were given some of the best storyline, dialogue and character arcs in the history of the era as well as creating some of the most memorable characters of all time.

This retrospective is to pay tribute to everything that made The West Wing a masterpiece and the performances were one of the biggest reasons it was. And while there wasn’t single regular in the original cast I disliked throughout the Sorkin era and all of whom lent various reasons to making the show great, I think the fairest way to do it is to recognize them in the order that they won their Emmys. In a sense the way that the Emmys works often helped the actors: there’s an argument that the year that they won each of their awards was the finest hour of the show in that season.

So we will start at the beginning with the work of Richard Schiff as Toby Ziegler, the White House communications director (“I’m a speechwriter” he kept saying throughout Season 1). And its fitting to start with him because almost from the moment we met him Toby was the most challenging character. Of all the characters on The West Wing, he was almost always in a case of perpetual unhappiness. And much of that may be due to his nature in politics.

Let’s start with a basic fact: of all the characters on The West Wing, Toby Ziegler only seemed to have two modes: miserable and angry. Indeed, one time when he came into The West Wing and said hello to Margaret, she was stunned: “You never say hello. You usually growl something inaudible.”

Toby chuckled because they had just managed to confirm Roberto Mendoza to the Supreme Court. The celebration was about to begin preemptively before Toby told the staff: “We will not celebrate until a majority of the Senate has voted which is” A small pause: “51 votes.”

Toby does not like to tempt fate.

“I will not jeopardize this by…” Another pause. His secretary: “Tempting fate.”

Toby marches taking the champagne away. “These things take patience. These things take luck. In the year since we’ve taken office, what kind of luck have we had?”

His secretary: “Bad luck.” Toby fixes her with a look. “Very bad luck.”

After the confirmation Toby was in such a celebratory mood that carried over until the next day. Then he told Margaret: “You on the other hand, should turn that frown upside down.” Margaret’s reaction was obvious: “Okay now you’re scaring the hell of me.” Toby then proceeded to walk through the West Wing singing: “Put on a Happy Face.”

I don’t think there was another occasion during the entire four seasons of the Sorkin era where I remember seeing Toby that clearly happy, even on the night Bartlet won reelection. Richard Schiff was remarkably gifted in making us see the humanity in a man whose default mode seemed dyspeptic on a good day, and furious every other day — and there were almost no good days in the Bartlet White House. This was in part due to the demanding nature of working in the White House, but there always seemed to be something deeper underlying Toby’s behavior and it has taken me a long time to realize what it is.

Toby Ziegler’s entire career in The West Wing was a mix of relentless forward momentum and combined arrogance. This is the nature of working in politics and quite a few of the other characters — Josh in particular — all had it to an extent. But there was something different about Toby’s attitude. Throughout the series run, particularly in the Sorkin era, he was butting heads with every single character, including the President, because they didn’t seem to be living up to their potential. He rarely liked compromises, he was never happy with whatever victories they won, he was always seeing the glass half-empty. I’ve mentioned this in a couple of my more politically based stories over the years but its worth looking at Toby’s background to see why.

Quite a few of the characters had backstories with tragedy but Toby’s was the most severe. In Holy Night, we learned that his father had been a gangster in Murder Incorporated and had spent much of his life in prison. Josh went out of his way to bring his father to the White House on Christmas Eve and Toby didn’t want to talk to him despite Josh’s pressing. (I’ll get to why Josh tried so hard when I deal with his character.) Toby was reluctant to even try.

Most of the characters on The West Wing had failed romantic relationships (Sorkin was never good with love stories) but Toby’s marriage had broken up not long after they won their first term. Toby’s wife was a Maryland Congresswoman named Andie Wyatt (Kathleen York) and throughout the first three season she and Toby had conversations but they were mostly friendly ones. In Season 4, it seemed like they were on the verge of reconciling as during the campaign he told the staff that Andi was pregnant with twins.

Toby with his ex-wife in…well, times.

For the rest of Season 4 he kept trying to convince the two of them to get married again and Andi kept being coy about it. In the penultimate episode of Season 4 Toby has bought a house for them to live in and is about to propose and Andi is clearly upset. Andi has been delaying answering for most of the season and she tells him why:

“You’re just too sad for me, Toby…You bring the sadness with you and you’re sad…You’re sad and you’re angry and you’re not warm. You take forever to trust people.”

Toby tries to argue that his father killed people for a living and not to worry about the kids. Andy says she does:

Because instead of showing them that the world is for them, you’re going to be telling them that they have to work hard in school so they can bone up for a life of hopelessness and despair.”

Toby: “Wouldn’t it be ironic if our kids were the only ones who were properly prepared?

Andie: “Toby I’m as serious as a person as you are and I’m able to see the glass as half full.”

Toby: “Great! Half full, half empty? Can we at least agree it’s not full yet?”

Like most spouses Andie has seen to the core of Toby’s personality during the Sorkin era and throughout the entire show. Toby has a job in the White House, makes the kinds of decision that can change the world and benefit millions of Americans. Throughout the series we’ve constantly seen him do this multiple times. But none of that ever brings him happiness or even momentary contentment. The President seems more happier and at peace some times then Toby does; we certainly see him get more pleasure from his job than Toby has.

This actually plays out somewhat better than most of the other characters after Aaron Sorkin leaves the show. As the second term progresses he begins to take things far more personally. When Josh chooses to leave the administration in the sixth season to campaign for Matt Santos, Toby is offended. “There’s more work we have to do,” Toby says. Josh counters: “We have to think about our ninth year.” When the primary campaign progresses Toby begins to write speeches for a female candidate to challenge the frontrunners including Matt Santos. Josh is enraged by this and Toby takes it personally that Josh didn’t invite him to the Santos campaign even though he refused to leave. Near the end of the episode Leo reminds Toby that he is still thinking himself as an outsider even though he’s the face of the Democratic Party now.

There’s an argument that Toby is the most leftist character in the Bartlet administration; he’s certainly by far the one who never likes the idea of compromising or meeting with opposing threat and always the first person who wants to pick a fight, whether with his own party or Republicans. A critical example of this comes in a Season 2 episode The Leadership Breakfast. This is basically a ceremonial affair just to acknowledge the beginning of the new session of Congress with leaders of both branches of government meeting. Bartlet is more concerned about having New Hampshire maple syrup than anything else about it.

But from the start Toby wants to talk about policy. He goes to Leo and demands they do. He puts it in terms of his marriage:

“This is what my ex-wife and I did for years, we had these rules, we could talk about anything but why we couldn’t live with each other.”

Leo is wary about it but lets Toby convince him to talk with the majority leader’s chief of staff (Felicity Huffman) because he knows her. Leo tries to warn him by using his marriage which has failed more recently.

“We couldn’t talk about it either. You know why…Because we loved each other and it was awful and we knew it was never going to change. Ever.”

It’s a warning but Toby ignores it.

In his meeting with Ann Stark Toby barely treats her with any respect. When Ann says that it’s a photo-op, Toby keeps talking policy. Ann outmaneuvers him to into Toby arguing that he will put an amendment on everything that moves. Ann says she’ll give him some room if they get a press conference on the hill, something C.J. is opposed too. Toby agrees to it.

When C.J. learns about it she is enraged by this and says that this makes the White House looks smaller. She tells him outright that this is a bad idea:

“I think the first visual we get is that Congress is the seat of power and the President is irrelevant. Not only that, you just took my legs out from under me with Ann!”

Toby orders her to. When the conference takes place, the majority leader isn’t on the hill because ‘he has a sore throat’. C.J. works out what happens and knows: “We’re gonna get hit.” We then get to see how Ann has planted the question with a reporter who basically quotes what Toby told her word for word.

One of the Congressmen gets up and tells the press this is disgraceful and begins to tear down the White House. Toby realizes what happened.

When Leo hears this he is infuriated about everything that unfolded and dresses down Toby in a way he rarely will:

“It was a breakfast. It was a damn photo opportunity. The year is one week old. The legislative session hasn’t begun and we can’t put a forkful of waffles in our mouth without coughing up the ball. You got beat.”

Toby realizes very quickly what happened. The Majority leader didn’t have a sore throat, so Ann took him off the board to fix the problem he created.

Toby: “When are you going to announce…that he’s running for President?”

Ann: “I’m pretty sure we just did.”

It’s the biggest setback Toby has but he never chooses to learn. That episode he and Leo form “the Committee To Re-Elect the President” and he spend the rest of the season preparing for campaign mode. This leads to one of the great moments of the show’s history “17 People.”

The Vice President has just made a speech cracking down on big oil and told Toby: “the tonnage of what I know could stop a team of oxen in its tracks.” He spends much of the next week trying to figure out what the Vice President is doing and he realizes that the Vice President has begun to campaign for President. He then confronts Bartlet in the Oval Office who tells him what we have known for more than a season but only fifteen other people know: that he was diagnosed with MS.

Toby’s reaction is to immediately challenge him, saying that there will be consequences that Bartlet has been unaware of, that he has been derelict in his duty. Bartlet reacts with rage, making inappropriate jokes and saying Toby is uncaring. But Toby gets to the heart of why he’s upset and what Bartlet has ignored by not telling the American Public:

“It will appear to many, if not most, as fraud. It will appear as if you denied the voters an opportunity to decide for themselves. They’re generally not willing to relinquish that right either.”

For the entire episode Bartlet has been fighting Toby. The moment he hears these words there is a long silence and he acknowledges it:

“It may have been unbelievably stupid. It may have been unthinkably stupid. I don’t know. I’m sorry. I really am.”

This discussion leads to the series fundamentally changing for the next season. There is a lot to discuss about it and I will probably do so in later articles but I’m going to focus on when it is resolved for the purposes of the campaign.

After taking a Congressional censure, Toby and Sam write a State of The Union address that seems to revive Bartlet’s reelection hopes. But in the very first episode dealing with the campaign setting during the Iowa caucus, Toby refuses to acknowledge either that they have survived a crisis that could have crippled their Presidency or that they have to take a different trope during the campaign. Instead he immediately starts to challenge everybody.

It’s worth noting that when we meet Toby for the first time in a flashback, he claims to be a very good campaign manager but he hasn’t won a single campaign he has been a part of and he fully expects to get fired from Bartlet’s run before it truly begins. Yet that win has given him a ridiculous amount of confidence in his own abilities, including over several more experienced campaign managers who come in during Season 3 to help run Bartlet’s reelection campaign. All of Bartlet’s staff clash with them but perhaps the most direct one comes in the first episode when Doug (Evan Handler in a too-brief role) lectures Toby. He’s talking about the whole campaign but it applies to Toby in particular:

“You guys are so pissed at him (Bartlet). You’re more pissed at him then the press is. You’re more pissed at him then the party is. You’re so pissed at him you’re pissed at me. Cause if he hadn’t lied, you could’ve run the campaign you always wanted to run instead of a bunch of people coming in here and teaching you not to bother anybody….I never drank the Kool-Aid, Toby. I came to win. And you’re so pissed at him you can’t even admit for the last two week, you’ve gone to sleep at night thanking God I did.”

Keeping with who he is, Toby remains silent…and it’s worth noting starting in Iowa he starts doing exactly what Doug tells him he wanted too, as well as continued to show that he is still pissed at Bartlet.

In the caucuses Governor Ritchie of Florida makes a comment about affirmative action then Toby wants Bartlet to respond to but everyone else in the campaign says they should ignore. Bartlet doesn’t want to move to his left and he spends the episode lecturing Bartlet on not making a stand. And says at the end of it: “He’s doing it again.”

That night Toby has a conversation with Bartlet in which he says the debate isn’t about affirmative action.

It’s between educated and masculine…or Eastern academic elite and plain-spoken.”

Bartlet: “It’s always been like that.”

Toby: “But a funny thing happened when the White House got demystified. The impression was left anyone can do it.”

He then argues about:

“The Two Bartlets — the absent-minded professor with the ‘Aw Dad sense of humor. Disarming and unthreatening, good for all time zones. And the Nobel Laureate. Still searching for salvation. Lonely, frustrated. Lethal.”

It is this discussion that makes me believe that Toby is the most leftist of the administration because he genuinely seems to think that the reason most Americans reject the educated is because they are idiots and that Americans only prefer the former because the latter doesn’t make the effort. This has never been true since Andrew Jackosn beat John Quincy Adams but it has been the view of the left for decades — and Toby has always taken that perspective.

Toby takes it further when he tells Bartlet something about the fact that his father used to hit him. The more Bartlet presses that is dangerous Toby keeps going and he says:

“It was because you were smarter than him. That’s why people hit each other. You were smarter than him,”

To be clear this is the most horrible psychology imaginable and Toby has stepped over the line in a way most people shouldn’t. Bartlet orders Toby out of the Oval Office and the truth is, Toby should have been fired.

But this is in keeping with Toby’s entire philosophy throughout his time on the show. He believes that campaigns should be about ideas and that the only reason they vote otherwise is because the appeal to their emotions. There’s a far greater argument that the world of American democracy is a popularity contest and not built on intellect. Perhaps that is why Toby is perennially in a state of unhappiness. He genuinely thinks that he is the smartest person, not only in the room but the world and he is miserable because no one else in the world can see reality the right way.

Maybe that’s the reason Toby is better suited as a speechwriter than as part of a campaign. He’s fine with a message but unlike almost everyone else in the West Wing, his idealism cannot approach political reality. I won’t reveal how the final season plays out because it doesn’t directly pertain to this article, but I will say by the end of the series Toby has been isolated from all his friends and colleagues because he believed he was convinced of his own righteousness as opposed to the national interest, something he has always argued for. Part of this may be due to Sorkin leaving the show but I think its keeping with the arc of who Toby is — someone who thinks he’s always smarter than everyone else until he wasn’t.

Richard Schiff, after leaving The West Wing, has worked constantly in both film and television. He had several guest starring roles in failed series such as a Criminal Minds spin-off and The Cape. He would land his first recurring role as a defense attorney in the first season of TNT’s intriguing procedural Murder in The First, play an OSS agent in Manhattan, a detective in the streaming series Rogue and another defense attorney in The Affair. For the last seven years he has played Aaron Glassman, the mentor to Freddie Highmore’s title character in The Good Doctor. There have often been variations to his work over time, but he has always been good at playing authority figures though sometimes you can’t trust them (as in his recurring role in the Dwayne Johnson series Ballers.)

I don’t what Schiff’s next major role will be, but honestly I’d like him to do a comedy and perhaps one where he gets to tell jokes instead of just deliver cutting lines. Schiff has been one of our greatest actors on the show, but I’d just to see him play a role where he is genuinely, unequivocally enjoying himself. Granted he does despair very well, but he should have as much fun playing a character as we do watching him.



David B Morris

After years of laboring for love in my blog on TV, I have decided to expand my horizons by blogging about my great love to a new and hopefully wider field.