Tear Jerker / Knights of the Borrowed Dark

“We live on borrowed time, Denizen. Our flesh turns to iron the longer we fight, but there's a change on the inside too.”
There was a quiet sadness in his voice. “I honestly don't know which is worse.”

Total warfare, eldritch horrors, and an author who loves torturing fictional children? Tragedy and horribly sad moments are a given.

Knights Of The Borrowed Dark

• Even though it's a Tenebrous, the Opening Boy. It's a manifestation of every child the other two members of the Clockwork Three have ever hurt, and it's sobbing is heart wrenching.
• Darcie blaming herself for what happened in Rathlath.
• Grey explaining to Denizen why Vivian acts the way she does—being a Knight is a hard calling, and full of trauma.
  Grey: You have to be iron. Inside and out.
  • Then Denizen tells Grey that he looks all right, and Grey just stares at him for a while before finally whispering, “Do I?”
  The moment dragged, giving Denizen what felt like an eternity to note the premature lines at the corner of the Knight's mouth, the bright, fractured coldness of his eyes. Old scars gleamed in the sunlight, the new ones shadows beneath gauze.
• How broken Darcie looks when Denizen comes looking for the Book of Rust.
• Denizen sees the second friend he's ever made shoot his only living relative right in front of him.
• Grey's state of despair when he explains his situation, made worse by the fact that he's actually crying.
  Grey: Don't. You know you don't have a chance against me. Don't make me hurt you any more than I have to.
• “Happy Birthday.”
• Learning that Grey was lonely—something he didn't show at all—from Mercy, of all people. And he was so lonely that he frequently came down to talk to her, despite her being a Tenebrous princess, and even brought her books out of guilt.
• D'Aubigny's death.
  • Jack's reaction to this.
• Vivian's whole cadre has been destroyed by the Clockwork Three again, and she shows no emotion.
  What must it be like? To be so long in a war that even this—a comrade fallen, her oldest friend a traitor, her home destroyed—was just one more obstacle to push past?
• The story of what happened eleven years ago.
  What did you hold on to when something hurt this much?
• Grey asking Vivian if everyone is dead, and them apologizing to each other before the fight.
• The Opening Boy's death, mostly the fact that it couldn't escape from the misery of the Clockwork Three.

The Forever Court

• The book wastes little time before bringing up what happened at the end of book one. And when it does, it's heartwrenching.
• The steel boxes metaphor for Denizen's Heroic Safe Mode. Seeing him wrestle with grief and guilt is bad enough, and the way he suppresses his emotions doesn't help.
  There was a place in the back of his head so remote and silent that even the fire of the Tenebrae flickered out before it could reach it. He imagined it sometimes as an oubliette lined with steel boxes—feelings left to starve and be forgotten. It was where he had pushed his thoughts about Vivian when there had been a world to save. There were boxes marked Crosscaper and Corinne.
  There was one marked Grey.
• When Mercy brings up Grey; apparently, not only did he bring her books, but told her stories, brought more books when she cried, and walked around Crosscaper and described it to her so she’d feel less trapped.
  • This seems to set off a Trauma Button for Denizen.
• “But you have to understand that I don't sleep anymore. I lie there, and I make the noises because I know you're listening, and sometimes that turns into real sleep and sometimes it doesn't. Because when I feel my eyes start to close… I imagine being back in Crosscaper. Asleep. Forever. With the Three getting fat off my fear.”
• The Redemptress’s story is tragic; She was building a life with the First Croit in Eloquence, but the Endless King sent the Order to stop this. They cast down their castle, sending Coronus into a long, deep sleep and leaving the First Croit broken by grief.
• Uriel loves Ambrel more than anyone else in the world, so losing her leaves him numb and hollow and broken.
  Uriel: I need to speak to Edifice Greaves.
• The Redemptress’s death. She was, at Her heart, just a grief-stricken widow, and Denizen was even trying to talk to Her before Uriel Croit launched his attack.

The Endless King

• Simon, when asked if he carries any scars:
  ‘Clocks,’ Simon said, without missing a beat.
  ‘What?’
  ‘Can’t. Be. Around. Clocks.’ Simon’s voice was as sharp as a new razor. ‘Spent a month hiding in an orphanage from Tenebrous. They had a thing about clocks. Now I have a thing about clocks.’
• Grey's reintroduction in Adumbral shows that he's been having a bad time ever since the end of the first book: he's thin enough that Denizen is immediately worried, his long hair and sharp suit are gone, and he looks exhausted, miserable and broken. He makes a valiant attempt at his old Stepford Smiler tendencies, but they aren't fooling anyone anymore.
  [...] but Graham McCarron was Grey to his friends, and it said a lot that it had only taken Denizen half an hour to find that out.
  Neither of them were those people any more.
• Vivian's death, making a Heroic Sacrifice to take down Dragon and let the others escape. Grey knocks Denizen unconscious so he doesn't have to watch his mother die.