Elder Scrolls: 10 Best Dark Brotherhood Assassinations
4. Permanent Retirement
The main antagonist to the Dark Brotherhood is the Imperial Watch Captain, and eventually, you get the orders to kill him off. Having constantly loomed over the entire beginning of the quest-line, there is a degree of justice in killing him off. But that's not what makes the quest really great.
It's that it can be incredibly difficult to pull it off without getting caught. He is constantly armoured and constantly under the protection of a bodyguard, meaning that catching him alone is near impossible. Breaking in to kill him while he's asleep is difficult and the rare occasion in which he takes a swim is really the only moment you have to off him with any success.
You have to plan carefully and really choose your tactics properly. Most of the other assassinations are as simple as sneaking up with a dagger and bob's your uncle. This one requires a degree of thought.