* JerkassWoobie: Alec. He does some pretty awful things (like picking fights with other swordsmen so he can watch Richard kill them) and he's regularly sarcastic, bitter, and cruel, even to people he loves--but once you've gotten a sense of just ''how'' screwed up he is and why, it's hard not to feel sorry for him in spite of his behavior.
* MoralEventHorizon: What Diane does [[spoiler:to Will]] in ''Tremontaine.''
** Lord Horn [[spoiler:raping Alec]] in ''Swordspoint''.
** Diane trying to manipulate the truth around Alec by telling him [[spoiler:Richard left him once it was known Alec was a Tremontaine]], until Alec [[spoiler:cuts his own hand open to remember what was true and what was a lie]]. He leaves and [[spoiler:never sees her again]].
** What Ferris does to [[spoiler:Artemisia]] in ''The Privilege of the Sword'' as well as his threats to Alec [[spoiler:regarding Katherine]] in the end. Alec [[spoiler:kills him]] for it.