Crazy Is Cool: Surprisingly, not Saito. He has his moments, but they're sporadic. Seki Cosine kinda steals the title for this fic. He sings, he dances, he punches you in the face, and then starts talking like Mr. Smith from The Matrix, then starts laughing like The Joker.
Iron Woobie: Saito. He was supposed to be a paraplegic, and what his mom did to him would leave a kid's mind shattered.
He references the actual incident a lot, but it's easier for it to stop being as annoying as it would normally get when you realize he's saying it in Sarcasm Mode.
Jerkass Woobie: More emphasis on "woobie" than "jerkass", but Saito has a mouth.
Alice. When you read her backstory, you'll feel pretty bad.
Lisa. Her mom died giving birth to her and her dad died in a plane wreck. Then her adopted father mostly ignores her and her brother, then when he finally starts paying attention, he directs it all to Saito, then she had to hear about how amazing Saito was while being compared to him. It pretty much justifies her being a cutthroat bitch and Green-Eyed Monster.