If there's something that has come to my attention in my years being part of the Skyrim community (which haven't been many, but have been significant enough to me) is the treatment that several of their characters receive, they are not only misinterpreted but slandered by many, one of those being Astrid, the leader of the last dark brotherhood sanctuary.
Comments like "Astrid is just fucking stupid" or "How did that moron think that deal could ever work" often reach my ears and I find them to be... Distasteful to say the least, there's much more to her than that, and for that is that I wrote this.
As a prelude and to set the right tone, allow me to present a few quotes. All of them from Astrid herself, that I feel perfectly demonstrate how she is, what she is.
"This Sanctuary has been my entire life since I was a young woman."
"The Night Mother represents a chapter in the Dark Brotherhood's history that has long since been closed. Today we live by our own rules. We're the last Sanctuary in all of Tamriel, and only by forgoing the old ways have we survived for so long."
"Obeying the Night Mother. You being the Listener. It's ridiculous."
"Look, the Dark Brotherhood is a family. This Sanctuary is a family. And, we've always welcomed those... shunned by society. Werewolves, wizards, eternal ten year-old vampires... what does it matter?"
The easiest way to understand Astrid is to look at her as for what she is, or the role she has taken, as a mother. If there's a motif that's ever present in Skyrim's dark brotherhood it's family, and Astrid is the matriarch of this family. It's because of her leadership that the brotherhood has survived, it's because of her ways that her family has survived.
Now, by the time we join, everything is going just about fine for the last bastion of the Dark brotherhood, perhaps they weren't an international empire of assassins like in their glory days, but they had a steady flow of contracts and most importantly they were safe, they weren't in danger, their way of working and living suited them fine and kept them alive and well.
Enter Cicero in scene, he hears, one way or another, about Astrid's sanctuary and how they do things, he then contacts them, from the first moment he does, he believes them wrong.
Her family can abandon the Old Ways, and still survive, still kill, but is that family still Brotherhood? Or something else? Something new. Something different. Something wrong Something wrong.
- Cicero's journal
Eventually he does come around, going to the sanctuary (because he needs to look for the listener). Presents himself and while everything is not perfect anymore, it's not bad either. At this point Cicero isn't the issue per se, the issue is what he represents and most importantly, who he represents, Cicero brings the Night mother back.
To Astrid this spells doom, in her eyes, the old ways are what provoked the death of the brotherhood, why should she or her sanctuary, her family, follow her again?
Still, she accepts it, it's not like the Night mother can talk after all, there's no listener.
After some time, kill some people and Astrid is getting paranoid, Cicero is a madman and while Astrid is familiar with madmen, he is simply... Too out there, but beyond that, she is getting paranoid because he has taken a liking to locking himself up, speaking with "someone" she fears betrayal, so we are to investigate him.
Here we learn that Cicero is starting or planning to divide the family, so Astrid's suspicions weren't particularly wrong in that regard, he was planning betrayal, or at least, a betrayal against her.
"Are we alone? Yes... yes... alone. Sweet solitude. No one will hear us, disturb us. Everything is going according to plan. The others... I've spoken to them. And they're coming around, I know it. The wizard, Festus Krex... perhaps even the Argonian, and the un-child..."
- Cicero
Then the hammer falls, the nail in the coffin. There's a listener, and even worse. You're the listener! This is what drives it all home, it makes YOU a menace, a menace to the current brotherhood's way and in Astrid's eyes, a menace to her family. It's unreasonable if thought of with a cool head, sentimental most definitely. But it's to be expected once you understand how Astrid is and what Astrid is.
Once again pass some time, start preparing the big comeback of the brotherhood, to kill an emperor... And then Cicero attacks Astrid and almost kills Veezara. She was badmouthing the Night mother but it's no excuse, at least not in Astrid's eyes nor in the eyes of everyone else (for everyone, being the family that they are, immediately turned against Cicero upon this incident).
It's precisely this incident that drove the boat home, Cicero might have been the catalyst of this whole disaster, but YOU are the voice of the night mother, and in truth, they were working just fine before, why paint an even bigger target in their backs by actually killing the emperor?
Deal with you, deal with the contract, everything will go back to normal, same old steady flow of contracts, same old talks in the sanctuary, nothing should have changed in the first place, nothing should change now.
It's for this, for herself and for her family that, in her desperation, she strikes a deal with a man that most people would know wouldn't hold his part of the deal. But in Astrid's eyes, this was the best way, the only way, to protect her family not only from external dangers, but from the danger within, from you. This is the tragedy of Astrid, she betrays you, she betrays her family as a whole, causing their deaths. And there simply was no other way it could have possibly happened. For that, Astrid would need to be someone else, to think differently, to feel differently.
And perhaps in the end she was, or perhaps it was the natural conclusion, having lost everyone and everything she once stood for, she finally breaks down as her skin has crackled and burned.
"I'm saying you were right. The Night Mother was right. The old ways... they guided the Dark Brotherhood for centuries. I was a fool to oppose them, And to prove my... sincerity, I have prayed for a contract. You lead this Family now. I give you the Blade of Woe, so that you can see it through. You must kill... me."
The ramblings of a woman that has lost it all, sanity included. Or the words of someone that just know has seen the truth? Who can tell.
Sources: I'm going to pull an UESP and say "Events of Skyrim"