He's practically a living martyr now. I know that's an oxymoron, but it's about as close as one can get to martyrdom without actually dying. FFS.
Could be he was selected to do all of these things, law school, book, job at Sidney, etc b/c he agreed to kiss the ring and become a full-fledged member of the DS, only to be playing them the entire time. Imagine what he knows. Also, friends close, enemies closer could apply here.
Too many schizonarios to consider for this anon.