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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
I Shall Wear Midnight
The future Coven of The Chalk has been introduced in this book

There are two new witches introduced in this book, two of them apprentices, and together with Tiffany they're going to form the Coven of The Chalk, just like Granny, Nanny and Magrat (and then the vanishing Agnes) were the Coven on Lancre. These new witches are Tiffany, who will fill the role of The Crone (she practically was born to be the crone, and it seems pretty evident she will grow up to be very close to the Weatherwax model even if having a bit of Nanny), Amber, who will go on to become The Mother, mainly because of her training under the kelda (she is said to be the closest a human can get to be a kelda, and a kelda is the perfect mother archetype). And Letitia, who will become The Maiden (yes, even though being married to the Baron, she has an innate maidenness). Previous Witches books have suggested that the role within the archetype of three has less to do with what the woman is, than with the witch's nature. After all, Granny could be both the crone AND the maiden, but there is no way she could be seen as anything else than the crone.
  • Moreover, given how many times it's mentioned that the Chalk lies directly between the mountains and Ankh-Morpork (which, we now know, has witches of its own), Tiffany's steading will become the new nexus of the continent's witch community after Granny Weatherwax retires or passes away.
  • I think having Letitia as the Mother and Amber as the Maiden fits better. I think the reference to Amber as a kelda refers to her spiritual affinity, not her fertility...
  • Actually this will be one well-balanced coven: all three of its members have the aspects of the Maiden, Mother, and... Other One. Amber has a very childlike way of approaching the world, but is trained under the motherly kelda - but the kelda is also one of the Fair Folk. Letitia, while appearing to be very much a maiden, will be the Baroness and therefore have the duties of watching over the people, and she helps out ghosts without even thinking - the Crone is the closest to Death out of the three. And Tiffany is most clearly the Other One, but she's, like Granny Weatherwax, as protective as any mother, and she was after all the first witch of the coven, practicing well before Amber or Letitia.

Eskarina's son

  • Is Preston.

  • Is not Preston, but will be the protagonist of a future Witches/Wizards novel, maybe even the last Discworld novel, on which Pratchett is already working, and which is to be released when he decides to end the saga. Eskarina is protecting him from the Auditors because of how powerful he is, he is even more powerful than a Sourcerer because he has control of non magic, not the absence of magic, but the exact opposite of magic -remember Simon's project at the end of Equal Rites; by the way, Simon is the father, obviously-, that could possibly destroy the Discworld. The Auditors will try to use him to end magic on the universe all together.

  • Is a witch.

  • Is Rincewind, due to the Timey-Wimey Ball.
    • You don't get much more anti-magic than Rincewind.
    • It makes sense! Rincewind's mother apparently ran away before he was born. How did she manage that? Time Travel!

  • Isn't Esk's and Simon's child, but Simon himself. In the course of their experiments in temporal metaphysics, he was accidentally youthened into an infant, and Esk decided to raise him as her adopted child rather than risk altering his age magically again. He needs her protection, because the UU wizards remember how he'd unwittingly endangered the world before when he was young, and are afraid he'll grow up to do the same thing over again.

  • Is Lobsang. Yes, this would mean that Esk became Time at some point. No, it doesn't have to make sense chronologically. Timey-Wimey Ball, remember?
    • See WMG page for "Thief of Time" for a different logical exposition wich supports the hypothesis tht Esk became as one with Time and wife to the great monk of Time- and mother of Jeremy/Lobsang

  • Is a Sourceror. Why are you all looking at me like that?
    • What is a Sourceror?
    • Wouldn't she have to have eight children? She only mentions one.
      • A sourceror, according to Discworld rules, is a wizard squared. If a wizard has a child with a wizard, then that child would be wizard x wizard or a wizard squared. This is usually impossible. However, we just so happen to have a female wizard here....
      • No, the eighth son of an eighth son will be a wizard and a sourceror is just the eighth son of an eighth son of an eighth son (i.e. the eighth son of a wizard). The child's mother... er, other parent does not have to have any magical ability whatsoever, otherwise Coin would never have happened. It's also been implied to be at least a factor in the wizard celibacy clause.
The Tiffany Aching tetralogy was written to line up with the four classical elements.
  • A very, very Epileptic Trees type guess: The Wee Free Men starred the Feegles living in the earth. A Hat Full of Sky had Tiffany learning to make titular hat of air. Wintersmith starred the being of water. And now, I Shall Wear Midnight has fire being an important element in the defeat of the Cunning Man. Coincidence, or just narratively satisfying parallel?
    • In the first two books, I'd take the elements more of being the fact that Tiffany is raised on the Chalk, and the talk of witches and stones. The Hiver, in A Hat full of Sky, is a creature of air.
  • Further WMG: "I Shall Wear Midnight" is NOT the last Tiffany Aching book, as they have not covered the element of Surprise.

The prisoner the Cunning man possesses is Carcer

  • Would explain the smile and the knives
    • Vimes wanted him to hang. Given that Vimes wanted it, I doubt Carcer stayed in the Tanty long.
      • Plus I doubt Vetinari would have much use for such a resourceful and uncontrollable villain. Carcer might be the Disc's equivalent of The Joker, but Vetinari is far too Genre Savvy to gamble the Tanty isn't a Cardboard Prison. Even if Carcer was found not guilty by way of insanity I suspect one of Vetinari's "dark clerks" would have paid a visit.
      • But wasn't he in the wing of people who were so evil that no hangman would hang them? Carcer does seem to be pretty close to the discworlds worst villain
      • The inmates name was explicitly stated as Macintosh. So, no, not Carcer.
      • Doesn't mean anything. Consider Moist von Lipwig and Owlswick Jenkins.
WintersmithWMG/DiscworldThe Last Hero

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