Among all the factions in Skyrim, the Dark Brotherhood is by far the most cryptic - and while a large amount of its secrets are unraveled as the Dragonborn becomes closer with the group, there is one mystery in particular that remains unsolved. Surprisingly, it isn't related to being the Listener, the reawakening of the Night Mother, or even Astrid's ultimate betrayal of the guild. Instead, it has to do with the first time players ever cross paths with Dark Brotherhood's leader herself.
Being kidnapped and waking up in a room next to three hostages, is a jarring, yet nonetheless fitting start to the quest line. After explaining that the Dragonborn stole the faction's kill on Grelod, she demands that they must end another life to repay the debt (much like how previous Elder Scrolls titles make Dark Brotherhood players kill someone first before being recruited). She claims that someone in the room has a death contract on their head, and that it's up to the player to determine which it is. As it turns out, she isn't lying - but the truth is much more complicated than it may appear.
It's Unclear Which Hostage Is Guilty In Skyrim's Dark Brotherhood Quest
Unfortunately, it's impossible to determine which of the three victims is the correct target in Skyrim. Upon being questioned by the player, each character provides a vague backstory that doesn't reveal much about their identity. Fultheim The Fearless, an ironically anxious Nord warrior, admits he may have gotten carried away in his past duties as a soldier. Alea Quintus, while brash, simply seems like a tired single mother who will do anything to provide for her children, which players can adopt in Skyrim. The Khajiit Vasha is perhaps the most logical choice of the three, as he boasts about his criminal history and even outright threatens the player.
However, regardless of which hostage (or hostages) the Dragonborn chooses to be their sacrifice, the outcome of the quest remains the same. Astrid will not confirm, nor deny, which character was the correct choice, and the player will be free to leave the Abandoned Shack. This is odd, because if Astrid's initial statement was true, then it's possible that the player could have spared the character with the contract on their head after all. Her careless demeanor makes little sense considering the gravity of the situation.
This quest, which is just as ambiguous as choosing Faendal or Sven in Skyrim, leads many players to infer that Astrid was lying to the player. Indeed, it's possible that not a single victim had a contract on them, and it's equally possible that each of them actually did - but it's impossible to prove or disprove either hypothesis. However, as Camelworks explains in a YouTube video, she is actually telling the truth: there is one person who does hold the contract, but it's not who players might think.
It's Possible Astrid Holds The Dark Brotherhood Contract In Skyrim
Interestingly, one theory is that Astrid herself actually holds the contract in the room. If players decide not to participate in her game and kill her instead, her dying words will be "Well done." This could be her way of accepting defeat, and praising the Dragonborn for their legendary skills in Skyrim, but it's also possible that she's implying that they cracked the case, and that she was the right target after all. Retrospectively, she is quite careful with her wording, saying that the person with the contract shouldn't leave the cabin - but Astrid could certainly fall under that umbrella, as well.
There is a large loophole in this hypothesis, though. Since the Dark Brotherhood fell apart after the events of Elder Scrolls 4: Oblivion, the members found in Skyrim are the last in all of Tamriel. Considering Astrid is the leader of the group, it's not likely that she would have accepted a contract against herself. It wouldn't make sense for a citizen of Skyrim to perform the Black Sacrament against her, either, as they would most likely be aware of her influential position in Skyrim's Dark Brotherhood, which has pros and cons in the context of the game.
Under a specific and borderline nonsensical set of circumstances, Astrid could possibly be the person with the contract. Similar to the three captives, though, players don't have nearly enough information to confirm or deny this theory. It may seem like this is where the trail ends. However, there is actually one other character who can be found in the Abandoned Shack, and unlike the rest, there is concrete proof that they are under a Dark Brotherhood contract. That character is the player themselves.
Skyrim's Dragonborn Has A Dark Brotherhood Contract On Them
As Camelworks explains, there is a contract out on the life of the player from the moment they step foot outside the Helgen Keep. As long as they have not yet joined the Dark Brotherhood in Skyrim, an assassin from the organization can randomly appear, attempting to take out the Dragonborn. The physical, written contract can actually be looted off the character's body after they've been defeated in battle - and the ill-intentioned note is signed by none other than Astrid herself. Not only was she aware of the contract, but she also was the one who sent the assassin out on their (unsuccessful) mission.
During Skyrim's infamous introductory sequence, the player is even implied to have been caught crossing the border to Hammerfell. According to Elder Scrolls lore, the Hammerfell region was the first to have cut its ties with the Dark Brotherhood. It's possible that the Dragonborn was aware of the contract on their head, thus deciding to seek sanctuary in a safer region but being caught by Imperials, which could change Elder Scrolls 6. It's unclear why the player would have been wanted dead prior to the events of the game, but it would certainly explain why they can be attacked by the assassin, even before they do anything of importance in-game.
Unlike the three hostages, or even Astrid herself, the player is the only person in Dark Brotherhood initiation sequence that is confirmed to have a contract on their heads. Astrid knows this, and yet, instead of killing them, she invites them to murder a (possibly innocent) civilian or two. Her intentions are muddled, but given her traitorous nature towards the end of the Dark Brotherhood story line, one can only speculate what she may have been truly planning in this absurd and mysterious Skyrim quest.
Source: Camelworks/YouTube