SPOILERS ARE UNMARKED, YOU HAVE BEEN WARNED!
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0 - New Spring
- Gitara Moroso's death following her Foretelling of the Dragon having just been reborn and heralding The End of the World as We Know It in the eyes of nearly everyone.
- The death and funeral of Tamra Ospenya, something that hit Moiraine even harder than the death of her uncle.
- Siuan catching up with Moiraine in the Borderlands and informing her of the mysterious deaths of Tamra's agents. Moiraine notes it's one of the few times Siuan has been genuinely afraid with no idea of what to do.
- Moiraine watching helplessly as a Black Sister throws three people, two of them children, over a balcony and to their deaths. It becomes her moment of My Greatest Failure.
1 - The Eye of the World
- Thom's Heroic Sacrifice at Whitebridge by throwing himself at a Fade to give Rand and Mat time to escape. Despite being ultimately subverted, both Rand and Mat feel guilty about it until they find him again later on.
- Afterwards, there's Rand being helpless to stop Mat's slow mental and physical deterioration from the corruptive power of his stolen, cursed dagger as they trudge their way to Caemlyn to (hopefully) reunite with their companions, dodging Darkfriends and other brigands all the while.
- The feeling of utter betrayal Rand feels after learning that Padan Fain had been the one to lead the Trollocs to the Two Rivers on Winternight.
2 - The Great Hunt
- Rand sees multiple possible routes his life could have taken when trying to activate a Waystone. The very first one he sees is heartbreaking: He stayed in Emon's Field and married Egwene the way he wanted, but he suffered from increasingly bad moods that something in his life was wrong Egwene found some way to quell them, but Rand ultimately outlived her. Rand becomes a half-mad hermit the rest of the village view with a mix of pity and fear. He meets his end as an old man joining a militia and charging into battle against a horde of Trollocs, finally finding what he was meant to do. Not only is it a sad life in its own right, but it drives home that there is no "normal life" for Rand.
- Rand's reunion with Thom, followed by Thom's life falling apart once again when his apprentice and lover is murdered. He's thrown into a Heroic BSoD that lasts well into the next book.
- Ingtar's Heroic Sacrifice at the end. Especially poignant because up until that point, he was a Darkfriend who was desperately seeking some way to atone for his crimes, and believed that recovering the Horn of Valere would lead to his salvation if he could lead the Heroes of the Horn against the Shadow, and then finally decided that he would seek his salvation instead by giving Rand and his friends the time to escape with the Horn.
3 - The Dragon Reborn
4 - The Shadow Rising
- The history of the Aiel certainly counts. It takes up chapters 25 and 26 of the book, and it is heartbreaking. Lewin's line at the end of Chapter 25 when he's exiled from the Jenn Aiel sums up the whole thing:
Lewin: I am still Aiel!
- It was heartbreaking reading Perrin's reaction to finding out that his family is dead, especially with everything that he risked to get to them quickly. It comes to a head when Faile gives him a Cooldown Hug to break him out of his shock and tells him to grieve, causing him to break down.
5 - The Fires of Heaven
6 - Lord of Chaos
- Rand having to give the order to have one of his Aiel friends and supporters, Mangin, hanged for breaking the law he set by murdering a Cairhienan man. He chews out Berelain and Rhuarc for saddling him with the painful decision of having to carry it out.
- When Elder Haman is marking all the Waygates for Rand and begins crying on the map for all of the Ogier-built cities and groves lost.
- Rand meets with Verin and Alanna in Caemlyn and feels like he's reuniting with a pair of allies. Alanna offers to remove his fatigue and he complies, only to find out she used the opportunity to Bond him against his will at the same time. Rand practically snaps from the feelings of being both betrayed and violated, learns that Moiraine's words to trust no one are right on the mark, and immediately retreats to Cairhien to attempt to get Alanna out of his mind and stop himself from killing someone out of the rage he's feeling.
- Nynaeve Heals Siuan and Leane from stilling, but Siuan also feels the death of her warder all over again from two books previous, causing her to cry at night.
7 - A Crown of Swords
- The first encounter with the gholam as it effortlessly kills several of Mat's men. He laments how one of them simply wanted to sleep in that morning and it became an un-granted last wish.
8 - The Path of Daggers
- Perrin's first bitter taste of the burden of leadership was back in Book 4 when he suffered an ambush and several of his men died. He gets his second when he has to make the hard decision to stand by his words by ordering several men hanged and forcing himself to watch the whole thing.
- Rand having to give a Mercy Kill to Fedwin Morr, one of the first Asha'man to join the Black Tower, who succumbed to the taint on saidin while guarding Min and whose mind reverted to a child's. Rand gave him a poison that allowed him to die in his sleep. While it had been brought up that Taim had had to do the same to others, this was the first time Rand had to.
- This is also one of the last examples of Rand's initial humanity prior to hardening himself further until the end of The Gathering Storm wherein, despite telling Taim to train the Asha'man as weapons, he yells at Taim for treating Morr like a statistic.
- The death of Adeleas. Her twin sister, Vandene, remains her normal calm and collected self when the body is discovered, as well as the following brainstorm session to try and figure out what happened, but the instant everyone leaves her alone with her sister's corpse, she loses control and starts crying out in pain and grief loud enough for everyone to hear anyway.
9 - Winter's Heart
- After Rand is bonded to Elayne, Min, and Aviendha, all three of them immediately begin to feel the constant pain he's had to put up with for months at this point from his never-healing wounds and feeling as though the herons branded onto his palms were still hot. The scene is from Min's POV and she immediately wants to begin crying while asking Rand, "How do you do it?" He really can't provide an answer.
10 - Crossroads of Twilight
- Perrin's torture of the Shaido captive, culminating in cutting off his hand...then walking away into the snowy woods in a Heroic BSoD before hurtling the axe as far as he can into a tree and leaving it behind. The talk he has with Elyas afterward is especially sad.
- Anaiya's murder by Halima.
11 - Knife of Dreams
- Learning that all of the people of Amayar committed mass suicide following the cleansing of saidin.
"The Amayar were all dead or dying. Men, women" her voice broke "children... Everywhere I have been, it was the same. They gave their children a poison that put them into a deep sleep from which they did not waken. It seems there was not enough of that to go around, so many of the adults took slower poisons. Some lived long enough to be found and tell the tale. [...]
"Have none been saved?" Zaida asked. "None at all?" Tears glistened on her cheeks, too, but Harine could not fault her on that. Her own cheeks were wet.
- A positive one as Nynaeve rallies as many Malkieri men to rally to and ride with Lan towards Tarwin Gap. The first few men she gathers, knowing they're about to ride to their deaths, still stand and cheer with, "The Golden Crane flies for Tarmon Gai'don!" This eventually proves to Lan that You Are Not Alone and the blood of Malkier is as strong as ever.
- Aram's continual unhinging and eventual death thanks to Masema.
- Vandene, still distraught over the murder of her sister, having taken to acting and dressing like her, getting her long-awaited vengeance. Doubles as a Dying Moment of Awesome:
Vandene: [As she stabs the murderer.] A gift from Adeleas!
- On a related note, the discovery that the missing Kinswomen whom were believed to have run away were killed by Adeleas's murderer. One of them had a doll from her childhood that she brought with her to the Tower and then everywhere else she went, hiding it carefully; the doll is found, proving her death since she would never have left it behind. Another? Reanne Corly, smothered in her sleep. Now she'll never get to be Green.
12 - The Gathering Storm
- The funeral. Faile and her retainers coming together one night to remember the Mera'din Aiel who watched over and protected each of them in Malden, ultimately at the cost of their own lives.
- Rand wailing in his mind as Semirhage is using the Domination Band to make him strangle Min.
- Verin's death. Similarly, her warder, Tomas, who opts to spend his final hour with his family.
- Rand's My God, What Have I Done? moment when he stops short of killing his father and nearly repeating the mistakes of his previous incarnation as he gets ready to destroy the entire world rather than continue fighting in a never-ending war against the Shadow. Luckily this turns into a Tears of Joy moment after he heals his mind, and he and "Lews Therin" become one again.
13 - Towers of Midnight
14 - A Memory of Light
- The moment when Logain's companions are turned to the Shadow and they have to fight their comrades, who are still on the Light. What is more, that nearly happened to Logain himself, and left him becoming unhinged for some time. Remember: that could happen to the whole world if Dark One got his freedom.
- The deaths of a good chunk of the main cast, including Siuan, Gawyn, and Egwene, along with plenty of lesser named characters.
- The moment when Logain gives up searching for the other male sa'angreal in order to help save the refugees from Caemlyn and their children from the Shadowspawn, and thus fulfills Min's viewing of "glory of men to come":
He had abandoned that power for what? To save these refugees? People who would spurn him and hate him for what he was. People who...
... who looked at him with awe.
Logain watched with wonder as the people flocked around his Asha'man, weeping for their salvation
. Elderly men took Asha'man by the hands, overcome, praising them.
Nearby, a youth looked at Logain with admiration. A dozen youths. Light, a hundred. Not a hint of fear in their eyes.
"Thank you," the young mother said again. "Thank you."
"The Black Tower protects," Logain heard himself say. "Always."
"I will send him to you to be tested when he is of age," the woman promised, holding her son. "I would have him join you, if he has the talent."
The talent. Not the curse. The talent.
HERE IS THE TRUTH, SHAI'TAN. YOU CANNOT WIN UNLESS WE GIVE UP. THAT'S IT, ISN'T IT? THIS FIGHT ISN'T ABOUT A VICTORY IN BATTLE. TAKING ME... IT WAS NEVER ABOUT BEATING ME. IT WAS ABOUT BREAKING ME. THAT'S WHAT YOU'VE TRIED TO DO WITH ALL OF US. IT'S WHY AT TIMES YOU TRIED TO HAVE US KILLED, WHILE OTHER TIMES YOU DIDN'T SEEM TO CARE. YOU WIN WHEN YOU BREAK US. BUT YOU HAVEN'T. YOU CAN'T.
- Oddly enough, Lanfear is the subject of a couple of these. Her confrontation with Rand in his dreamshard, where he reveals to her he does not love her and never did, is rather heartbreaking, and she almost, almost relents, allowing him into her mind and coming this close to coming back to the Light. In the end even Rand pities her for not knowing love and in fact being incapable of ever feeling it because of her need for power. Then near the very end when she once again falls her into The Starscream pattern and attempts to get Perrin to kill Moiraine, so she can kill Nynaeve, claim Callandor, and use Moridin's power to make Rand kneel while saving the Dark One from him and thus earning the greatest power she can possess, Perrin is forced to kill her. She had gone so mad from isolation, loss of love, pride, and desire to rule that she had to be put out of her misery... but it's still quite tragic. It's also an in-universe example since Perrin, still under Compulsion to love her, cries over her body.
- Fridge Horror also sets in when taking into account everything Perrin did to rescue Faile from the Shaido over the course of several earlier books to prove his devotion to her were all to prepare him for this moment. If he had abandoned the rescue mission, would he have been able to break the Compulsion?
- Each time one of the Great Captains realize they have betrayed the light due to Compulsion is rather heartbreaking. These are good and great men who serve the light willingly and are prepared to die for Rand and the world, and then they realize that they have been forced to betray their men and their oaths. Each one is different but when they realize they sent good men who trusted them to die is terrible.
"Suddenly, Olver felt a deep warmth. He had lost so many people, but one of them... one... had come back for him."
Gawyn: You won't be [left without a brother]. You have another brother, Galad. One you do not know. A son of... Tigraine... who went into the Waste... Son of a Maiden. Born on Dragonmount... Don't hate him, Galad. I always hated him, but I stopped. I... stopped...
- "Rand's" funeral, especially for those who don't know he's not really dead. Tam's words hit hardest as he can only really repeat his words of So Proud of You to his adopted son.
- Also Moiraine, who simply echoes what had been believed in-universe to have been her own last words, in the letter she left Rand in Cairhien: "You have done well, Rand." And caresses his face.