User blog comment:Wolfishtail/The civil war, which side would a race not native from skyrim or have a ruleing body chose?/@comment-5357218-20120813183840/@comment-5357218-20120813190448

I'm sure they would, but you could still choose to fight for the Empire. Loyal to the death, and all that jazz.

On that, it wouldn't even be possible, since you play a new character/prisoner in every game. In an expansion sure, I could see that. Though I think the plot required to flesh that out would pretty much have to be the focal point of the expansion/DLC etc, otherwise it would be too big to properly explore, and it would soon find itself on Milkman's List: http://elderscrolls.wikia.com/wiki/User_blog:The_Milkman/Skyrim%27s_Smorgasbord_of_Shortcomings