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.
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.
Red Country
Despite the fact that he is essentially the main antagonist of the book, Nicomo Cosca's Villainous Breakdown and subsequent death at the end of Red Country are surprisingly tragic. His last scene shows him as a pathetic, dishevelled wreck of a man who lost all his wealth and power and has to resort to taking innocent children hostage in a desperate attempt to reclaim at least some of the gold that was taken from him. After Temple, who is no longer intimidated by his former boss, gives him a brutal "The Reason You Suck" Speech, Cosca actually starts crying, revealing himself as a sad old man who threw away every chance at genuine happiness in his life and whose greatest desire is to turn back time and start all over again.
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?
The Age of Madness
The Dogman's funeral in The Trouble With Peace. It's attended by a huge crowd of people, and practically every single one has a story of how he helped them or gave them courage.
The Wisdom of Crowds has one of the most powerful death scenes in the franchise with the hanging of King Orso. He's one of the most unambiguously good people in the series, someone with all the makings of a great king, and he's killed by the very man he showed mercy in front of the woman he loves. Yet in spite of his impending death, he never loses his dignity or sense of humor, only faltering once when he tells the crowd in attendance it's looking to be a beautiful summer, "For you, at least." He then regains his composure long enough to tell the watchers he wishes them no ill-will, and when he notices the executioner putting his hand on the lever he takes the opportunity to declare his love for Savine one last time.
"Well! I think I'm being given the signal to finish up. To my sister, Savine..." He grinned over at her. The way he used to, when they were together, in Sworbreck's office. When he had just thought of the best joke. One he knew she would love. That was how he wanted her to think of him. As he had been. As they had been. "I take some comfort in knowing you'll be a far better ruler than I ever was. We have had our differences, but you remain the woman I most admire. And, let's be honest, the only one I've ever loved." He was gratified to see a tear slide down her cheek. It was not as if it had all been worth it, for one tear, but it was something. He grinned at the Lord Regent. "To her husband, Leo dan Brock, I can only say...how's your leg?" He gave one last chuckle, and it became a sigh. "Let's get on with it," he said. There was a clatter as the trap dropped open.
