Since all the words in the market have been mixed up, a salesman shouts “Done what you’ve looked.” Nobody can say anything understandable until the stalls are put back up. As the merchants set to sorting out all the spilled words, Officer Shrift, Dictionopolis’s one-man police force, appears. He’s only two feet tall, but twice as wide. He blows his whistle constantly—when he’s not blowing, he’s shouting at people that they’re guilty. Officer Shrift scolds Tock to turn off his alarm and then asks who’s responsible for the mayhem. He says the Humbug looks suspicious. As the Humbug defends himself, he points to Milo.
People’s inability to speak coherently until the market is put back together again is humorous because it makes an abstract idea (not being able to spell words correctly) more literal. Officer Shrift is, in many ways, a caricature of a policeman—and he seems just as nonsensical as everyone else in Dictionopolis. The Humbug is, of course, partially responsible for the mayhem, so Officer Shrift’s suspicion is warranted. But as the Humbug essentially blames Milo, things get even more ridiculous—Milo is, of course, an innocent child.
Officer Shrift says that, just as he expected, “boys are the cause of everything.” Officer Shrift won’t let the Humbug elaborate and turns to interrogate Milo. He wants to know where Milo was on July 27. It’s Officer Shrift’s birthday, and when Milo asks why this matters, Officer Shrift mutters that Milo forgot his birthday. He then reads Milo’s crimes (which include upsetting the applecart and mincing words) and asks if Milo is ready to be sentenced. Milo points out that only judges can sentence people, so Officer Shrift changes into a black robe and says he’s the judge too. Milo asks for a short sentence, so Officer Shrift gives him “I am,” the shortest sentence he can come up with. He also gives Milo six million years in prison.
Everything that Officer Shrift charges Milo with is absurd, but it does introduce readers to some new idioms: “upset the applecart” means to ruin plans, while “mince words” means to speak vaguely. In this content, though, Officer Shrift means the phrases literally, as he’s describing what happened in the mayhem at the market. Notably, Officer Shrift, not Milo, is the one who’s figuratively “mincing words.” Milo’s impossibly long sentence is also ridiculous, which shows again that logic and reason barely exist in Dictionopolis.
When Milo points out that only jailers can put people in prison, Officer Shrift again changes his clothes—he’s the jailer too. He leads Milo and Tock through a huge door and into a dark corridor. They climb down a circular staircase. The walls are slimy, and cobwebs brush Milo’s face. Officer Shrift shows Milo through another big door and says it’ll be lonely, though Milo can always talk to the witch. Milo is terrified as he follows the officer deeper into the prison. They reach a cell door, and Officer Shrift opens it for Milo and Tock. He promises to see them in six million years and then walks away.
The nonsense in Dictionopolis has severe consequences for Milo—he’s being imprisoned for something he didn’t do, for an absurd amount of time. Milo doesn’t have any control of the situation and feels like all he can do is follow along. In this way, Milo is beginning to understand the consequences of illogic and of not understanding the world around him. Things become even scarier when Officer Shrift mentions the witch in the dungeon—Milo seems to assume that this witch is going to be the stereotypical Halloween variety.
Milo and Tock decide this is very serious. They also realize there’s nothing to do, but Tock says they’ll figure it out. He asks Milo to wind him and as Milo complies, Milo muses that you can get in trouble if you can’t spell, or if you mix up your words. He vows to learn more about words if he gets out. A woman’s voice across the cell deems this a “commendable ambition.” Milo looks up at an old knitting lady. He warns her to be careful; supposedly, there’s a witch down here. The lady says she is the witch. Milo leaps back in fear, but the lady laughs because she’s a Which, not a witch. Her name is Faintly Macabre, and she’s the not-so-wicked Which.
Milo is again confused here by the homophones “witch” and “which.” To be fair, using “which” in this context is as ridiculous as everything else in Dictionopolis; there’s no way he could’ve prepared to meet a Which in the real world. But as Faintly Macabre introduces herself, Milo starts to learn not to make assumptions. She looks like a perfectly nice old lady and, at the very least, doesn’t look like the terrifying witch Milo seemed to expect—her name suggests that she is only “faintly macabre,” or slightly scary. And she supports the novel’s insistence that people should, whenever possible, try to learn something.
Confused, Milo asks what a Which is. Faintly Macabre explains that she’s the king’s great-aunt. She used to get to choose words for all sorts of occasions in her capacity as the “Official Which.” At first, she encouraged people to use the right words. But then, “power corrupts,” so she tried to keep as many words for herself as she could. Sales in the market fell, but the Which continued to hoard words. With fewer words out there, casual conversation became difficult—until finally, the Which insisted that “Silence Is Golden.” People stopped talking, and the king ultimately put the Which in prison. They still haven’t appointed a new Which, which is why people think it sounds intelligent to use as many words as possible. She warns Milo that it’s inappropriate to use too few words—but it’s worse to use too many.
As Faintly Macabre essentially tells a story about the ills of censorship. She frames herself as someone who was selfish and, to indulge her selfishness, tried to keep people from using words. And this had serious implications: not only could people not communicate, but it also plunged Dictionopolis into a depression. Now, Faintly Macabre advocates for balance, rather than using language excessively or carelessly. She insists that people should choose their words carefully and make sure they’re saying things in the clearest way possible. Using too many, as the king’s cabinet does, just obscures the words’ meaning.
Faintly Macabre returns to her knitting and says she’s been down here ever since. People have either forgotten her, or they think she’s a witch—but they’re just as frightened of witches as they are of Whiches. Milo insists she’s not frightening. To this, the Which says that Milo can call her Aunt Faintly and offers him a sugar-coated punctuation mark. Milo vows to help her, but the Which says only one thing can help: the return of Rhyme and Reason. She says it’s a long story, but Tock says they’d love to hear it.
Since people in Dictionopolis no longer bother to choose the correct word when they speak, it makes sense that they don’t see the point in distinguishing between a witch and a Which (and that they’d be afraid of a person whose entire job it is to choose the right words). When Tock says they’d love to hear a long story, it’s an endorsement: spending one’s time listening to stories like this is, per Tock, a good use of one’s precious time.