Board Thread:Lore Discussion/@comment-17045460-20130609055613/@comment-10873599-20130817170757

Here's the way I saw it. This is my theory, so just hear it out.

After the Hero of Kavatch became Sheogorath, he decided to try his hand at the arena. He was powerful, and worked his way to the top. Obviously, a guy like this would make some real enemies- eneimies that would turn to the Dark Brotherhood.

Cicero was origanally assinged to another target in the arena, which explains his appearance there, disguising as a normal citizen. Cicero took the contract and awkwardly changed his attitude towards HoK/Shegorath, but no one, not even the victim, noticed it.

When Cicero killed his target in the wilderness, HoK/Shegorath returned to Oblivion. To avenge his avatar's death, HoK/Sheogorath cursed Cicero with madness. Unfortunately, this turned Cicero into an even more determined killer, and he was soon so respected, that he became the care-taker of the Night Mother, and was (somehow) blessed with an extended life to serve her... or whatever that creepy thing is.