Al Swearengen: Tell E.B. nothing.
Richardson: I'll just keep quiet.
Al Swearengen: No. Tell E.B. nothing's going on and then tell him, "If I wanted to tell you anything, I'd have told you. Don't send the imbecile over with no more notes."
Richardson: I can't remember all that.
Al Swearengen: Can you remember "Nothing's going on"?
Richardson: Yes.
Al Swearengen: Tell him that, then.

Al Swearengen: That they're armed and awake don't have to mean they're fucking hired.
Dan Dority: Yeah, and when I feel a shit coming on I'll remember to drop my pants.
Al Swearengen: The obvious merits utterance. Character is fucking pertinent.
Dan Dority: If I'm to go, I'd as soon get started before the darkness.
Al Swearengen: Going means the darkness is upon us.

Al Swearengen: What makes you think any good will come of confronting Hearst now?
Seth Bullock: Now is when he's killing people.
Al Swearengen: What, you feel he'll leave off soon?
Seth Bullock: Tactics and timing ain't the issue.
Al Swearengen: The hell you say.

Al Swearengen: [Hearst] makes of me and Tolliver a two-headed beast to savage what might be healthy borne out of the fucking election and gnaw its own privates off-hours. Plans keep coming to the cocksucker, that their final sum is this: but for what brings income to him, break what he can; what he can't, set those parts against themselves to weaken.

Al Swearengen: [reading a telegram from Hawkeye] "23 men hired, all on our way." This squaw-fuckin' idiot. Proves in eight words he's incompetent and a fuckin' liar. He can't have got Adams' telegram more than four hours ago, yet he expects me to believe that in four hours he can prudently assess the qualities of 23 hires. And you know what "on our way" means, huh?
Blazanov: No.
Al Swearengen: "On our way" means they're getting drunk and blown in some saloon in Cheyenne and running their mouths about the big fuckin' filibustering expedition they're being commissioned for under the command of the famous Hawkeye; the laziest, most shit-faced whore-mongering cocksucker to ever piss my money away!

Al Swearengen: [discussing Custer at Little Bighorn] I'll tell you this, son, you can mark my words, Crazy Horse went into Little Bighorn, bought his people one good, long-term ass-fucking. You do not want to be a dirt-worshipping heathen from this fucking point forward. Pardon my French.
Joanie Stubbs: Oh, I speak French.

Al Swearengen: [during a meeting with Johnny Burns, E.B. Farnum, and Jimmy Irons] I wanna know who cut the cheese. [nobody answers] I'll tell you this for openers: we are gonna set off an area on the balcony. [opens the door to the balcony] And God help whoever doesn't use it, because the next stink I have to smell in this office, and whoever doesn't admit to it is going out the window, into the muck, onto their fucking heads, and we'll see how they like farting from that position, okay?

Al Swearengen: [on Bullock and his affair with Alma] He don't know if he's breathing or taking it in through fucking gills; he is that fucking cunt-struck. They're afloat in some fairy fucking bubble, lighter than air. Him, her snatch and his stupid fucking badge.

Al Swearengen: [to Adams] Get a fuckin' haircut. Looks like your mother fucked a monkey.

Al Swearengen: A man, as it happens a rival of mine, learning the secret of a great man's lieutenant would make that lieutenant his slave. My rival knows that expanding the circle of the informed, diluting his power, will confound his intention, so he takes precaution to be the sole sharer of his secret. Then the world being the world.. along comes a half-assed knight-errant, Utter, Hickok's ex-partner, to put all my rival's plans at risk. I'd seek audience with Utter, verify my thinking. He earns his bread shipping packages. And as the dimwit nobility that made him intercede may now make him reticent, you, Chief, will be my prop and ploy whilst I seek to draw him out.

Al Swearengen: Announcing your plans is a good way to hear God laugh.
Season Two

Al Swearengen: As damp as your hands are, why do you continuously lick your fuckin' thumb?
E.B.: Habit, I suppose.
Al Swearengen: Could you learn the habit of lickin' a fuckin' stump?

Al Swearengen: Before a guilty verdict would get executed on that cocksucker, three men would walk in that meat locker where he's bein' held with bags over their heads and cut his fuckin' throat. And within half an hour, that celestial's little pigs will be on their backs with their hooves in the air, belching up human remains.
Judge: Are you saying you'd order that to be done?
Al Swearengen: I'm sayin' I had a vision it'd happen. My second of the day. First come when I was watchin' you and them lawyers on line this morning. They began to slither in my sight like vipers. So as not to puke, I had to close my eyes. The vision went on. Got worse. I saw the vipers in the big nest in Washington. They were takin' us in the camp for actin' like we could set out own laws up or organizations and then saw the big viper decide to strangle and swallow us up every fuckin' thing we gain here. It was horrible. How could we fuckin' avoid it? How could we let the vipers in the big nest know that we didn't wanna cause any fuckin' trouble?
Judge: And that's when you had your second vision.
Al Swearengen: Yeah, the cut throats and the pigs. But who wants all that blood spilled, judge, huh? Isn't there a simpler way of not pissing off the big vipers?

Al Swearengen: Before his present troubles and whilst you pursued your preferred activities, your partner Bullock joined in a campaign to which I hope you will now subscribe.
Sol Star: What do you mean my, "preferred activities"?
Al Swearengen: Oh, a reference to your people's penchatn for money-getting. A poor attempt at wit.
Sol Star: I don't find those funny.
Al Swearengen: I apologize.
Sol Star: If you want my help, don't insult me.
Al Swearengen: Oh, Jesus Christ, show me the secret grip that proves my regret and let's be about our fucking business.

Al Swearengen: Dan's a fucking expert. When he's not shit-faced drunk, so's Ellsworth.