- You'd think the book would harden the reader's heart to the point of invulnerability, but there are a few moments that manage to sting. Like any time the Named Men hold a funeral.
- The end of Before They Are Hanged, specifically the Dogman's final words at Threetree's grave. Back to the mud, old man. Fare you well.
- In the same scene, he also gives a brief but moving eulogy to Cathil, despite having known her only for a short time.
- There's also Black Dow's uncharacteristically heartfelt eulogy at the funeral of Tul Duru. And if you think about it, the fact that he doesn't get one after his own death in The Heroes.
- It's impossible not to feel sorry for Jezal at the end of Last Argument of Kings: He's stuck in a political marriage with a woman who despises him while the woman he really loves is married to a man he finds absolutely repulsive, one of his closest friends is slowly and painfully dying of radiation poisoning after being exposed to the Seed, and his hopes of using his new authority to make the Union a better place are brutally crushed when it turns out that he's nothing but an expendable Puppet King and will be disposed of if he doesn't comply to Bayaz' commands.
- Nicomo Cosca's death in Red Country definitedly counts, despite his evilly affable villainy during the book.
- Lamb's Heel Realization in Red Country. Especially bad if you've read the first three novels and know that this isn't the first time Lamb / Logen has tried to become a better man, and that this is likely not just him admitting that he's fallen back into his old ways but him concluding that he will never be able to fully leave them behind.
Lamb: I don't... feel evil. But the things I done. What else can you call 'em?