This book is essentially a 200 page freewrite. Kerouac wrote with an impressively total lack of restraint:

I lay in bed thinking I was going to be a big hero of New York with rosy features and white teeth—an idiomaniac post-Iddyboy incarnation of the American Super Dream Winner, Go Getter, Wheel,—and white snowy scarf and big topcoat with corsaged girls in tow and no teetotaller I but big journalistic champion off of Times Square (like The Little Theater) as I had seen in newspaper tragedists in B movies talking over beers in stale barrooms of neon winking Manhatten night (166)

I shit you not, this sentence goes on for another 200 words. And this is not some cherry-picked example of Kerouac writing more loosely than normal; Kerouac keeps up this pace for the entire book. Every comparison, every piece of figurative language he could think of, he put in, and then he put in some more for good measure. 

The book ostensibly follows a boy’s love affair with a girl from his small town, but really it follows the chaos of Kerouac’s prose. Sometimes an extended metaphor or simile carries away a page or more before it finally reluctantly returns to the characters in the story.

Thus, the characters themselves are not that compelling. I found it difficult to feel the main character’s feelings of camaraderie, love, innocence, loss, or any of the other emotions that Kerouac tries to imbue into the text, because these emotions are obscured—rather than heightened—by thickets of figurative language. 

At times, though, I got flashes of what Kerouac’s prose could be with more editing. 

Her body was like fire, packed soft and round in a soft dress, young—firm-soft, rich—a big mistake—her lips burned all over my face. We didn’t know where we were, what to do. And dark moved the Concord in the winter night.

I much prefer this excerpt from the one above. Kerouac has pared down his writing a bit, which allows us to see an image of young love quite clearly and amplified by his figurative language—the lips burning, the body packed soft and round into a dress, and the juxtaposition of the Concord river, of rustic small town life. 

But Kerouac mostly writes like the first excerpt throughout the book. As a result, Maggie Cassidy can be difficult to follow. At times you feel like you’re swimming through prose with no clear idea of what you’re supposed to be seeing or feeling. The book could have been much more compelling if Kerouac had edited himself more.

Also, on page 61 there’s a drawing of a chessboard. It just sits there on the corner of the page. In any other book this would have jarred me out of my reading flow state entirely. But it feels right at home with the weirdness and wildness of Kerouac’s writing.