User blog comment:Spritydove/Deeper Thought into the Civil War/@comment-1889545-20120617091315/@comment-4692902-20120617094158

Don't forget that there seemed to be a good chance Skyrim could have simply separated ties like that if Ulfric had asked Toryyg to try and leave the Empire, instead he killed him, and as Tullius put it, "Plunged Skyrim into chaos!", causing a lot of unnecessary deaths and weakening both sides further, this has and several other bits of information has cemented in my mind that Ulfric's top priority is only to become High King.

I agree that if you're going to separate then do it early and quickly, to reduce the damage. But from what I know the Empire even with just Skyrim and High Rock has the best chance of getting rid of the immediate threat (obviously the Dominion), then just Skyrim by itself.

I think it would be best to try and get all the other races and countries aboard, but right now it seems like the most readily available country to join the Empire right now would be Hammerfell, and I know the Medes kinda burned that bridge, so they aren't going to be joining the Mede Empire at least anytime soon.

Maybe if the Dragonborn were to try and claim the throne, that might make them a little more open to joining. Of course trying to convince other countries would be rather difficult as also, oh well, I can dream.