WittyReference said
He's the guard captain, right? He'll probably be a badass in his own right and also surrounded by likeminded individuals. Now, if you could spread the guards a bit, it might make things a bit easier. Enlist some pickpockets and thieves, some brigands are bar brawlers, get enough trouble started in distant parts of the city and the guards'll be forced to respond. The downside to this is of course, with such an orchestrated timing, he'll know something's up and be ready for you. Checks and balances, pick your poison on if you prefer a firing squad waiting for you or a small elite group of badasses.
Well in Dervs briefing (correct me if I'm wrong Almighty One) the captain himself doesn't appear to be much of a threat. He just sends out his guards to do the dirty work. And it was mentioned that it would have to be "quite the disturbance" in order to get enough guards out of the guard house to allow somebody sneaky to get inside and kill him.
At first I was thinking we'd have to cause a mass revolt in the populace, but a bunch of smaller isolated incidents that spread the guards out could work well too, and would cut down on civilian casualties which the Resistance would appreciate I'm sure. Even still, it would have to be a lot of small incidences that are still drastic enough to get a decent amount of troops called. Petty crimes and bar brawls wouldn't really work that well.
Maybe fire bombing gov property or something.
And I can't imagine every guard being an elite fighter. Sure the Lieutenants maybe, but it just doesn't make sense for all the guards to be master swordsman, even if they are Redguard.