After he forced the lieutenants to read Robert's Rules of Order.
My favorite part of the series is when String realizes he's been conned by Clay Davis, and tries to put a hit out on him. Avon intervenes and scolds String, saying "what I tell you about playin' them fuckin' away games?" Avon (and later, Marlo) understood that they could never go legit, because going legit is just another unfair game with a different set of rules.
The only character that escaped their fate was Bubbles.
One of my favorite moments in that scene is hearing Avon say "You'd need a day of the jackal motherfucker for that" and Googling that phrase and discovering and watching the amazing movie of the same name. Thus realizing even more just how perfect that line was in context.
The Wire definitely took attention to detail seriously.