Alright, it is 2 in the morning and my brain is buzzing, let's get unnecessarily deep into analyzing the political ramifications of a character on a fictional world! Minor game spoilers for some quests below, so keep that in mind.
Please note, I am not pro-Stormcloak. Not too fond of the Empire and Dominion/Thalmor, either. Having said that, if the events of all the sidequests are cannon, and the Dragonborn is assumed to be a Nord like in the promotional materials, it is likely that in future events, the canon victors of the Skyrim Civil War would be the Stormcloaks. Word wall ahead, prepare to absorb that knowledge (heh).
Exhibit A: The Emperor's death at the hands of the Dark Brotherhood. The emperor's death would more than likely destabilize the Empire itself and loosen its grip on the province of Skyrim. We can also say with some level of confidence that this emperor either did not have an heir or had many heirs that were all viable candidates to succeed him. Either way, we know for a fact that if the player is to sign up on the side of the Empire after killing the Emperor, the pledge is no longer to Emperor Titus Mede II, it is to an unnamed Emperor. If the Emperor had a single legitimate heir, that heir would be named in the oath. But they are not. The death of the Mede would likely destabilize the Imperial Province of Cyrodiil, much like the death of Septim did following the Oblivion Crisis.
Exhibit B: "Skyrim Belongs to the Nords". Love him or hate him, the challenge between Torygg and Ulfric was lawful. The main argument against Ulfric is that he murdered the king with a Thuum. Who else uses Thuums regularly during their quest? The Dragonborn. How many times have you been accosted by a guard telling you to stop, because that "Shouting" is making people nervous? They also say that there are no laws against shouting. Having said all that, it doesn't change the fact that the war took place, or that the Stormcloaks are xenophobic pricks, and has nothing to do with whether or not they could win the war, so I digress.
Given player agency, it is impossible to say for certain whether or not the Dragonborn sides with the Empire or the Stormcloaks, but player agency isn't in effect here. Remember, we are working under the assumption that the Dragonborn is a Nord. Nords, as a whole, do not like elves. They deal with the Dunmer of Morrowind, they dealt with the Snow Elves back when they were arriving from Atmora, and they are dealing with the Thalmor trying to outlaw their most prevalent god during the events of TESV, who was also, during mortal life, Dragonborn. Player agency be damned, a Nord is far more likely to side against the Empire, and with them the Thalmor and Dominion, and thus, side with the Stormcloaks.
Exhibit C: The Dragonborn's Actions throughout TESV. During the course of the game, the Dragonborn does a number of quests that, in one way or another, undermine the strength of the Thalmor and the Empire, the biggest of which being the assassination of Emperor Mede. Another example of this is during the main quest Diplomatic Immunity. The Dragonborn infiltrates the Thalmor Embassy and (if you play the way most people do) kills a lot of Thalmor soldiers. The Embassy, being so far from the Dominion homelands of Summerset, is not in a position to easily call for more forces. Another instance of undermining the Dominion's authority comes from the quest Siege on the Dragon Cult. An Altmer man named Captain Valmir sits in front of a ruin, dressed as your ally. He tells you to seek the masks. When you come out of the ruins, is dressed as the enemy, telling another person to do the same task he told you. He does not work for either side, he is a Dominion spy. You then bring about his death. This thwarts the plans of the Dominion to claim the masks.
I have typed for a while and my brain is running out of juice. If any of you have anything to add to this discussion, please do. Am I wrong? Am I right? What details did I miss? Let me know what you all think.
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© Post "The Canon Victor of the Skyrim Civil War" for game The Elder Scrolls.
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