Toby: [to his twin newborns] I didn't realize babies come with hats. You guys crack me up. You don't have jobs, you can't walk or speak the language, you don't have a dollar in your pockets, but you got yourselves a hat, so everything's fine. I don't want to alarm you or anything, but I'm Dad. And for you, son, for you this will be the last time I pass the buck, but I think it should be clear from the get-go that it was Mom who named you Huckleberry. I guess she was feeling like life doesn't present enough challenges to overcome on its own. And honey, you've got a name now, too. Your mom and I named you after an incredibly brave, uh... An incredibly brave woman. Really not all that much older than you. Your name is Molly. Huck... and Molly. So, what do I do? Well, you're going to need food and clothes and doctors and dentists... there's that. And should you have any questions along the way... I'm going to be doing stuff like this, Huck, 'cause you're leaking a little bit out of your mouth there. You holding my finger, son? Hey Molly, your brother's holding my hand. You wanna hold my hand?

Toby: [to Josh, about leaving to run Santos' campaign] You can't leave. We're not done here.... You're going to walk into the Oval Office and tell the President you just found a better horse?

Toby: [to Leo] You're like the guys who say, 'Are you telling me you could only find one African-American speechwriter good enough to work at the White House?' I'm amazed I found that many. 'Good enough to work at the White House' is a pretty small population to begin with. And guys who can write entire sections of a State of the Union? I'd be as surprised if there were as many as nine of us. And Sam was one of them.

Toby: [to Sam] You're gonna lose, and you're gonna lose huge, they're gonna be throwing rocks at you next week, and I wanna be standing next to you when they do.

Toby: [to Will] Listen, when you get home tonight you're going to be confronted by the instinct to drink alone. Trust that instinct. Manage the pain. Don't try to be a hero.

Toby: A couple of things. I need you to look at a couple of answers on defense readiness. I need concrete examples of waste in Pentagon procurement. We need two more members of the IRC for post spin. I need you to fill out this marriage license and paperwork for a joint checking account and review this 60-second answer on Rwanda.
Andy: Okay, okay, okay and um, under no circumstances, and sure.
Toby: See, by my count, you said under no circumstances to the IRC post spin and sure...
Andy: I said under no circumstances to marrying you again.
Toby: May I ask why?
Andy: I have the unique experience of having done it once before.

Toby: All right... It couldn't have gone far, right?
Sam: No.
Toby: Somewhere in this building... is our talent.
Sam: Yes.

Toby: And they're sending in a team of lawyers to look into it?
Will: Yeah, but we're scrappy.

Toby: Arnold Vinick just positioned himself as Jed Bartlet's natural successor.
Annabeth: How'd he do that?
Toby: Without one mention, without so much as an allusion to either one, he managed to dismiss Russell and Santos as puny dwarf-like children trying to get a seat at the grownups' table.

Toby: Call and response isn't going to work in front of a Joint Session. You're alliteration happy: 'guardians of gridlock,' 'protectors of privilege.' I needed an avalanche of Advil. And when you use pop-culture references, your speech has a shelf life of twelve minutes. You don't mind constructive criticism, do you?
Will: No, sir.
Toby: Anyway, thanks for coming in. I told Sam I can do this by myself.
Will: Well, maybe he thought that your speeches were obscurantist policy tracts lost in a cul-de-sac of their own internal self-righteousness and groaning from the weight of statistics. I'm just speculating. I can't say for sure.
Toby: [pause; laughs to himself] A 500-word stanza on American leadership in a globally interdependent age that moves beyond triumphalism by this time tomorrow. If it's 501, don't show it to me.

Toby: He's a featherweight who only looks like a lightweight because he's got you propping him up.
Will: He's the heir apparent.
Toby: Don't say 'heir apparent' when we have men in moon suits hermetically sealing the Oval. This is Russell's only shot... A night like this.

Toby: I don't think a strong executive is such a good idea... Half the faculty at Yale Law describes the American Presidential system as one of this country's most dangerous exports... It is a recipe for constitutional breakdown!
Lessig: Well, I can see this is going to be a vibrant discussion.

Toby: I feel like I've lost 180 pounds. I am smiling, I am laughing, I am enjoying the people I work with - I gotta snap outta this. What's on your mind?
Mandy: I want you to help me get the Chinese to give us a new panda bear to replace LumLum.
Toby: Well that did the trick.

Toby: I just figured out who you were.
Kiefer: He's gonna say Satan.
Toby: No, you're the guy that runs into the 7-11 to get Satan a pack of cigarettes.

Toby: I throw a rubber ball against the window; that means you come to me. As my frustration level grows, so does the velocity of the ball against the window.
Will: Don't you ever worry about the window breaking?
Toby: During moments of peak frustration: when the Speaker of the House threatened to repeal the 16th Amendment, a couple of Yankee games, and when Congress censured my boss...but it's always held up, that window; that window is a game-day player.