This may belong in the spoilers section, but I shant divuldge said spoilers - if people know what I'm talking about, hopefully they'll know where I'm coming from.

I am pro-Empire. I won't debate my reasons why, and yes I've done the Stormcloaks - a few times, in fact!

However, I have one deviation from the usual pro-Empire schtick (that I've seen, at least), I actively WANT to persue the end quest of the Dark Brotherhood, because I feel it's *necessary* to help fix the problems surrounding the Empire at the moment. I do other things as well that kind of force the Empire to react more fluidly, I don't always side with them on quests so long as it won't lead to an active downfall of the organization as a whole.

Is this hypocritical of me? To swear the Legion Oath and go against it so dramatically once "no one is looking", to actively root out traitors and treason in the midst of my chosen faction while simultaneously being one of the worst?

Anyone else do it?

...You're a Dark Brotherhood assassin and you're worried about an oath, too an empire of man? You are doing it wrong.

It's not just that. I willingly (from an roleplay standpoint) subject an Imperial supply ship to be hijacked and plundered just so I can draw out more of a pirate band that's claimed far, far, far more than that as notches in their belt. I help the Gray-Manes just to inspire more anti-Thalmor sentiment and put another soldier in the field to oppose them (despite the fact logistically I'd end up killing them later as a member of the opposite faction.)

Things like that. The end of the Dark Brotherhood line is just the proverbial "Big One" in a field of other strategic demolitions.

Unless the Empire/emperor has any secret plan to deal with the Thalmor, being pro-Imperial is useless. And even so, not sharing it with the resistance in Hammerfell/Skyrim is, at best, a bad idea. And at worst, an opportunistic attempt.