Okay so obviously we can choose sides in the war, Imperial or Rebels. I am sure most people here have seen the achievements, but if not, there is one called 'Hero of Skyrim' and it is a reward for 'Capturing Solitude or Windhelm'. Solitude is the Imperial 'base' and Windhelm belongs to the rebels. My question is, what happens to the leader of the opposing faction when we capture their city? For instance, Ulfric Stormcloak is not only the leader of the stormcloaks, but Jarl of Windhelm, and usurper of the throne of the High King. Assuming we joined the Imperial Legion and captured Windhelm, what do you think would happen to Ulfric? Would he be a boss battle? Captured and executed? Would he surrender? Assuming he was dethroned of both his positions as High King and Jarl, who would fill those positions? Is it possible that the player could become Jarl/ Military Governor of whatever city they capture? These are just a few speculations I was having earlier today, feel free to comment and add your opinion

Becoming the Jarl for the city you choose to take over sounds like a good idea/possibility to me.