Obi never talked much about his past, nor did he really want to. He would never explicitly state what he did, only ever imply it to be illegal, and involve assassination. His new life, as a guard and messenger were cozy. And peaceful. He wanted no part of his past life any longer, but...the past has a way of coming back to haunt you. Just as you had started to haunt the hallways of the castle, posed as a servant. Obi had worked alongside you in the past, if he hadn't kept his distance you two would of been friends even. But he left the business, and you, without a word.