Times where an antagonist rejects an offered opportunity to redeem themselves in Literature.
- Nevyn from the Deverry series urges his enemies to repent at various points in the story, because he knows that if they don't, this will have severe consequences in their next life. Most of them refuse his offer of redemption, but he notably gets through to Sarcyn.
- In Dragons of Requiem, Dies Irae almost has a Heel Realization when Benedictus calls him by his childhood nickname, which spurs a few childhood memories. He quickly disregards them and resumes attacking Benedictus.
- In The Dresden Files book Skin Game Michael Carpenter asks Nicodemus to abandon his service to his Fallen Angel, telling him to look at the path it's led him on. This comes shortly after Nicodemus has sacrificed his daughter, likely the only person in the world he actually cared about. For a moment Nicodemus seems tired, uncertain, and then he laughs. He declares that he's not a puppet of the Fallen, but that after two thousand years they follow him, and that he's forged his own path of war and plague through the ages. True to the second part of the trope, Michael then goes at his foe with all his might, not holding back at all.
- In Going Postal, the book ends with Reacher Gilt being offered a similar choice to what Moist was offered at the start. Vetinari tells Gilt he can either carry out a risky government job (in this case, sorting out the Royal Mint) or he can walk out the door and "never hear from me again." Unlike Moist, Gilt walks away. Unlike Moist, Gilt does not manage to avoid falling to his death through the hole in the corridor floor.
- In Harry Potter and the Deathly Hallows, Harry, after seeing Voldemort's ultimate fate, urges Voldemort to feel remorse for his crimes in order to make his soul whole again. Seeing as feeling remorse had a high probability of killing Voldemort and given how terrified Voldemort is of dying, the Dark Lord refuses and unknowingly damns himself in the process.
- The Heartstrikers: When Julius defeats the Evil Matriarch of his clan and tries to reformat them into a more peaceful, democratic organization that doesn't kill each other on a whim, he decides to spare his mother, since killing her would be hypocritical. She hates him for this, and the only reason he is able to keep her from being Stupid Evil (much less actively trying to kill him) is to lock her in a Magically-Binding Contract. While at first she has a lot of success getting her other children to try to kill him for her, it doesn't take long for her power to slip away as they all realize how crazy she really is. By the end, she's little more than a figurehead kept around because of tradition, but she's still yelling about how she's right and Virtue Is Weakness.
- Grima in J. R. R. Tolkien's The Two Towers is offered the chance to redeem himself by fighting alongside Theoden, the king he has betrayed, but Grima just snarls and slinks away to Saruman.
- Saruman himself, thrice : first at Orthanc after his army has been defeated, second, after the war when he meets Gandalf and the Hobbits on they way home, then last after the Battle of Bywater.
- Also part of Sauron's backstory in The Silmarillion. After the War of Wrath and Morgoth's defeat and exile, Sauron was genuinely repentant at first, and did want to return to Valinor. Unfortunately the price of redemption proved to be too high for him. Having gotten a taste for power as The Dragon to the Lord of Evil, Sauron wasn't about to settle for much less, let alone whatever penance the Valar were surely going to impose on him for his rebellion. So instead he vanished into the unknown east of Middle-Earth for the next thousand years, returning in the guise of the sorcerer Annatar, with a Master Plan to manipulate everyone into helping him conquer the world.
- Lucifer in Paradise Lost - "he would rather rule in Hell than serve in Heaven".
- In The Scarlet Letter, Hester talks Chillingworth into realizing that he has hurt Dimmesdale, but he later ignores that realization.
- Harold Lauder from The Stand uses this trope when the Boulder Free Zone not only accepts him but begins to regard him as a hero. He realizes full well he has a choice between putting his childish grudges aside forever or holding onto them, even though he knows that they're poison. In the end he decides he's carried his hate for too long to just let it go, and joins up with Flagg. As he lies dying after Flagg decides he has outlived his usefulness, Harold finally lets go of his hate and writes an apology to everyone he hurt/killed before shooting himself.
- In Star Wars: Darth Bane: Rule of Two, Zannah's cousin Darovit offers her more than one chance to turn away from the dark side. She pretends to accept his final offer, then uses Sith sorcery to drive him insane and convince the Jedi Order that he is the Sith Lord they've been hunting.
- In the last book of The Wheel of Time, Rand tries to convince his Evil Counterpart Moridin to abandon the Shadow and help him defeat the Dark One. Moridin throws it in his face-after all, the Dark One has promised him oblivion, for himself and the world, and Rand can't offer anything that would tempt Moridin more than that.
