The Dark Tower: The Wind Through the Keyhole Part II

Last week, we began The Wind Through the Keyhole with a major storm and another of Roland's stories. This week, we get a story within a story within a story! 

In Wizard and Glass, we discovered that Roland had accidentally killed his mother and returned a crystal ball from Maerlyn’s Rainbow to his father. His newest ka-tet—Jake, Susannah, Eddie, and Oy—are following The Path of the Beam when they encounter Marten, now calling himself Randall Flagg, in a twisted version of Emerald City. Roland just misses killing Flagg but managed to gun down Andrew Quick, aka Tick-Tock Man, who was working for Flagg.

The Wind Through The Keyhole was written to chronologically follow Wizard and Glass even though it was released in 2012, long after the 7th novel, The Dark Tower (2004). For that reason, we have decided to continue Roland’s adventures in sequential order since Stephen King calls it The Dark Tower 4.5.

Come join us … before the world moves on.

*Remember: While this is a reread, please avoid spoilers in the comments. The point is to get there together!

This is a shorter book with only five sections, so the plan is to split the book into three parts (about 100 pages each) and meet here at our usual time (Tuesday at 12 p.m. ET) to discuss major themes, motifs, and reactions. Make sure to bookmark the HQ page for the schedule and links to all of the chapter discussions as they go live! This week, we get a story within a story within a story! Join us in the comments for a discussion of Part II of The Wind Through the Keyhole: The Wind Through the Keyhole!

CrimeHQ's The Dark Tower Reread

The Wind Through the Keyhole

Our first read of The Wind Through the Keyhole ended with Jamie en route to the jail cell, bringing in suspects for Bill Streeter to eyeball in hopes of discovering the true nature of the Skin-Man. Meanwhile, Roland stays with Bill in the cell—where he is being kept for his protection—and begins spinning another tale to comfort the boy, as well as pass the time for himself. So, we have King telling the story of Roland, telling a story to his ka-tet of his younger self, of him telling a story to the boy Bill. Okay—here we go!

Roland begins: “Once upon a bye,” a boy named Tim, his mother Nell, and his father Big Ross lived on the edge of the Endless Forest. When Tim was eleven, his father, a woodsman, was allegedly killed by a dragon along the Ironwood Trail. After a time, Big Ross’s close friend and fellow woodsman, Big Bern Kells, comes calling for Nell’s hand in marriage. She’s at a crossroads because Covenant Man is due soon to collect the taxes, and if Nell can’t pay she and Tim will be tossed out to live in the wild. So she accepts her husband’s friend’s proposal. Shortly, Kells shows his primitive side.

That night, long after midnight, he was awakened by a thump and a cry that might have been part of a dream, but it seemed to come through the wall from the room his mother now shared (true, but not yet possible to believe) with Big Kells. Tim lay listening, and had almost dropped off to sleep again when he heard quiet weeping. This was followed by the voice of his new steppa, low and gruff: “Shut it, can’t you? You ain’t a bit hurt, there’s no blood, and I have to be up with the birdies.”

A bright aside for Tim is when he goes to the cottage of Widow Sai Smack to learn mathmatica and other basics. But, his stepdad quickly pulls him out of school to work at a sawmill making money for the family.

When the Covenant Man arrives on horseback, he surprises them not just by raising the taxes, but also directing Tim—not Kells—to hand him the money. When the boy nears, Covenant Man lifts him up into the saddle, covertly handing Tim a special key and telling the boy that it can open any lock, once. He further steers Tim with his words to check into his stepdad’s locker, which Kells never opens in front of either Nell or Tim.

At his first opportunity, Tim uses the key on the locker and finds the lucky coin that his father had promised to give him one day, bringing into question Kells’s personal account that Big Ross had been killed by a dragon. 

Tim goes to the Covenant Man and ends up having dinner with the taxman. Using the gearshift of a Dodge Dart as a magic wand, Covenant Man waves it over a bowl of water, conjuring up an image of Tim’s home and Kells beating his mother because the locker had been opened. Tim wants to run to save his mom, but Covenant Man has one more heartbreaking item to share with the boy and sends him off to a nearby stream.

Lying six or eight inches below the surface was a human body. The clothes were only rags that floated in the current. The eyelids were gone, and so was most of the hair. The face and arms, once deeply tanned, were now as pale as alabaster. But otherwise, the body of Big Jack Ross was perfectly preserved. If not for the emptiness in those lidless, lashless eyes, Tim could have believed his father might rise, dripping, and fold him into an embrace.

Tim returns home and learns his mother has gone blind from Big Kells’s blows. The Widow Smack is there caring for Nell, and she warns Tim not to return to the Covenant Man (who I had assumed, and I bet you did too, is Randall Flagg). She says he’s an advisor to the palace lords in Gilead and “He’s made of lies from boots to crown, and his gospels bring nothing but tears.”

It’s mentioned that Flagg never ages and does this Covenant Man routine as a hobby. But why? I understand a demon’s main job is to wreak havoc, but with the proletariats? Stephen Deschain, sure, that makes sense, but messing with the downtrodden seems like a job fitting of a lesser evil spirit, not the top dog. Unless, of course, Tim turns out to be a linchpin. So, let’s read on.

Word spreads, and kindly neighbors help clean up Tim’s house, taking turns watching after Nell so the Widow Smack can rest. Tim finds the Covenant Man’s magic wand and a pail, which he assumes has been left for him. He waves the wand over the water to behold Flagg and a sighe, a fairy named Armaneeta, taking him to Maerlyn of Eld’s house where he is led to believe that Maerlyn will gift him an item that will restore his mother’s vision. So, Tim plans to travel in search of the famed wizard. The Widow Smack doesn’t want him to go, but knowing he will anyway, she presents him with a gun for protection.

Illustration by Jae Lee.

He should have listened to the good Smack (sorry, couldn’t help that fellow readers) because it is a trap, with the naked Tinker Bell-from-hell leading him on a wild ride to the end of the Ironwood Trail where he almost gets sizzled by a real fire-breathing dragon. Later on, he’s being stalked by alligators that have trapped him on land. As one crawls forward, Tim drops to one knee and triggers a round into the beast’s eyes.

Nearby mudmen—swamp dwelling mutants—begin to cheer thinking Tim is a gunslinger. Tim asks them about Maerlyn, and the leader of the mudmen hands him a device to continue his trek. The electronic gizmo (engineered by North Central Positronics, of course) switches from red to green to keep him moving northward, as does a voice called “Daria.”

Down the trail, Tim come across a tyger in a cage. He frees the big cat and administers a few drops of a magical potion, conveniently left close by, and lo and behold, the tiger shapeshifts into a human—none other than Maerlyn himself. Grateful, Maerlyn gives Tim the remaining healing potion to restore his mother’s eyesight. The therapeutic liquid does the trick, but when he goes to tell the sleeping Widow Smack, he finds her throat has been sliced. Kells comes out of hiding and begins choking Tim to death. With her sight restored, Nell plants her husband’s ax into Kells’s head, killing him … thus, ending Roland’s long night of storytelling.

I was prepared to dislike another extended spinoff that would pull me away from the main Eddie, Susannah, Jake, and Oy storyline. King had made it work with Cuthbert and Alain, but a divergence of what amounts to a fairy tale about a boy named Tim Ross …? Oh, me, of little faith. King accomplishes this narrative feat in the blink of a tiger’s eye, leaving the reader wanting more backstory of the connections between Flagg and Maerlyn (and even the naughty Armaneeta) and willing to travel down any new captivating sideline of horror and suspense that may split from straight shot along the Path of the Beam.

But next, back to Roland in a jail cell with the shapeshifter known as the Skin-Man coming his way.

What do you think of the story of Tim Ross? Head to the comments and start/join the conversation!

*Remember: Be careful with your comments—NO SPOILERS! We will be moderating the comments and deleting anything we feel is a spoiler, so pause before you post and make sure you're not ruining it for someone else.

The Dark Tower Reread Navagation
The Wind Through the Keyhole Part I | Index | The Wind Through the Keyhole Part III


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David Cranmer is the publisher and editor of BEAT to a PULP. Latest books from this indie powerhouse include the alternate history novella Leviathan and sci-fi adventure Pale Mars. David lives in New York with his wife and daughter.


  1. Alan Williams

    As a story in it’s own right I enjoyed the tale of Tim, but what I really wanted was to continue the tale of the Skin Man or even better the Ka-tets journey along the beam. The skin man tale is at least some backstory to Roland, but do we also need backstory to Flagg? It feels to me like King dropping a short story into the middle of a novella to pad it out. Maybe for me reading this in the original published order would have worked better?

    i don’t know but this just didn’t work for me.

  2. Adam Wagner

    Trust me, reading this now is the right “order.” I decided to read the series 1-7 and then try and go back to The Wind Through the Keyhole, and it was extremely difficult. After completing the exhaustive journey, trying to go back and pick up with these characters again seemed out of place.

    That said, I enjoyed the story of Tim Ross. It was whimsical and fun, with some decent parallel’s to Roland’s own journey but contrasting in important ways. I also liked seeing how Gilead was viewed from outside sources.

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