I know everybody hates on Toby for this one, however, it is so incredibly well written and filmed. It represents the true dilemma of how we need tremendously competent and intelligent people in charge of these important positions, however, because the average American can't see themselves within these people, they are no longer voted for or hold them. Being incredibly smart and intelligent is often a burden, and incredibly isolating.

Toby may have been out of line, but sometimes you _need_ people, friends, confidants to cross that line and hit you where you're the weakest, force you confront your greatest fears, and tell you to stop holding back so you can achieve your full potential. Bartlet's family love him too much to do that. The other staffers revere him. His enemies would have exploited him. Toby was one of maybe two people in the world (the other being Dr. Keyworth the psychiatrist) to push Bartlet like this, and Toby knew it. It takes guts to be the bad guy. This scene and many others is why Toby is one of my favorite characters ever.

Toby did overstep here, but I also think the genius of this scene is that he risked his job to lay the foundation in Jed's mind that Ritchie was the same type of man his father was - an ignorant bully in a position of power that cows all those around and under him into dismissing his ignorance so long as he keeps winning. You see it in the debate episodes, and you also see it in the scene where Ritchie shits on him before a shared campaign event for being a smart liberal elite who thinks he's better than everyone else. Toby's pre-gaming here, he's not trying to piss Jed off for the sake of being edgy - he's trying to do what *someone* should have had the balls to tell Hillary in 2015: never underestimate your opponent.

If the show was just Bartlett and Toby in a room talking, I would have watched 10 seasons of it.

People will say Toby crossed the line. Toby crossed that line for the love he had for Bartlet. This scene showed what Toby would do and even sacrifice for that love.

"Thank you Mr. President. And I'm taking the bourbon with me."

Toby's the best actor in the whole series. Has the best lines in the series too. Other actors were good, but the Toby character beats 'em all. Hands down.

Weird resentment from a lot of the commenters here towards Toby. The man saw a threat to his boss' job, understood why his boss wasn't pushing back, confronted his boss and lit a fire that kept the show on the air for several more seasons, even after he himself had been kicked to the curb. And for all that, Toby "crossed the line" when he signed the contract to work for the Commander-in-Chief of the most powerful network drama and television history.

What I always find fascinating about this scene is that obviously the President could order one of his staff to immediately leave the Oval Office the moment he even came close to going there. But in this scene Toby had so gotten under his skin that he didn't. And with the comment about a 'Brooklyn Shrink's office' showed that he was very aware of what just happened.

This is why Toby has the leak never made any sense. This Toby Ziegler would never betray Jed Bartlet like that

Toby chewed Jed up and spat him out. Such invasive and incisive psychoanalysis. When Jed asks, "Why are we talking about this?", his head is bowed, as though he was beseeching Toby to stop oppressing him. Powerful scene!

Imagine being described like that. “The Nobel laureate. Still searching for salvation. Lonely. Frustrated. Lethal.” It’s testimony to Bartlett’s intellect that someone even as accomplished and intelligent as Toby would refer to him as a mind that was dangerous. Then you watch Bartlett humiliate Richie in his debate.

It's fascinating, because on one hand there's a valid point here, but on the other hand it's a perfect example of how Toby often gets so caught up in his cause that he ends up making it in possibly the worst way, because he just doesn't fully get how people work outside of his own moral positions. It's interesting to compare this with his debate about affirmative action with CJ in the same episode where he similarly just gets so caught up in his own righteousness, his own need to be win the debate and have his viewpoint affirmed as the unambiguously correct one, that he just doesn't acknowledge the personal angle and just keeps prodding and prodding until he realises too late that he's just completely trampled over the other person and their feelings.

Toby could've said the point better by just being more direct about it. "I think you have a blind spot with this guy. I don't think others will say it and so I am, I think you want to reconcile your differences with him and he's the type to drive all opposition into the ground. You're smarter, don't compromise or be passive with this guy. I think you have an instinct to." Don't put out the Brooklyn shrink thing.

every President needs someone in their inner circle who will challenge them and not just be yes people

I don't know who are you or why you are uploading all these The West Wing clips on KZfaq, but bless your heart: you are a joy to see on my homepage

That excuse me was threatening lol

So Toby keeps the glass. ;-)

Thank you

Even though I adore The West Wing, the writers would tend to push the boundary of imaginable and walk into the ridiculous. This would have never happened. Zeigler would have been transferred to a PR post in Yemen. But...because we love drama...it becomes memorable for the viewers. I totally get it.

Martin Sheen never won an Emmy for this role!!!! The world sucks

This helps the case that toby leaking later DOES make sense.

What does his family signing the Declaration of Independence got to do with him potentially having an ethnicity problem?

I think Toby was way out of line with all of this.

Toby had very, very few good moments. This definitely wasn't one of them. I did not miss him in the final season at all.