Colson Whitehead’s marvelous Cool Machine (2026) is the third in his series of Harlem crime novels. They feature Ray Carney, the street-smart owner of a 125th Street furniture store and a sporadic fence who is often in trouble. Cool Machine reminds me again that New York City is not one city. It is, instead, a conglomeration of many cities that sometime overlap. Whitehead’s trilogy, which included Harlem Shuffle (2021) and Crook Manifesto (2023), has its center in the Harlem world of hustlers and criminals and business people and strivers and family men, but those people intersect with gem merchants of midtown Manhattan, the changing world of the Lower East Side, Radio Row in lower Manhattan, a part of the New York scene that was demolished with the construction of the World Trade Center. Some of his other books also show us the differing New York City worlds. Sag Harbor is about a tony part of eastern Long Island, but it is also about the world of the privileged living on Manhattan’s Upper East Side and its culture of exclusive private schools. And his The Colossus of New York is a marvelous prose poem, something of an ode to the many “cities” of New York City.
Reading Whitehead makes me think of the cities within the City that I inhabited or entered into during my more than half-century in the City. But it also brought to mind some other authors. The cover of Cool Machine reminds us that Whitehead has won the Pulitzer Prize for fiction…twice. He is one of the few writers who have won more than once, but the kudos go further. Yes, he won a Pulitzer for his 2016 novel The Underground Railroad and again three years later for The Nickel Boys, books much different from the Harlem crime trilogy. However, he also was awarded the National Book Award for The Underground Railroad, and he has been the recipient of many other honors. This got me thinking about the twentieth century writer who won a Pulitzer Prize for fiction, a National Book Award for a different novel, and two Pulitzers for drama, Thornton Wilder.
Today Wilder is largely overlooked, even though many of my generation have read the Pulitzer-Prize-winning The Bridge of San Luis Rey, an innovative, powerful work. And many of us have seen or read or even acted in his innovative, powerful play that won a Pulitzer: Our Town. On the other hand, I have never seen his other Pulitzer-Prize winning play, The Skin of our Teeth, although I would have liked to have seen the original Broadway cast of it, starring Frederic March and Tallulah Bankhead. Now there’s a pair.
Some years back, I found that our library in the country, the Barrett Friendly Library, had a copy of Wilder’s The Eighth Day, which won the National Book Award four decades after Bridge won the Pulitzer. It is very good, and that made me wonder why he wasn’t read much these days. Even so, I did not seek out more of his output or reread Bridge, and perhaps it is telling that I could not recently remember the title of The Eighth Day nor could I tell you a lick about it other than I remember it as being a good book.
These thoughts returned when I plucked Theophilus North, Wilder’s last novel, published when he was 76, out of a leave-one-take-one book kiosk. I enjoyed reading it and read more about Wilder, an astonishing man. In addition to the Pulitzers and the National Book Award, he was awarded the Gold Medal for Fiction from the American Academy of Letters and the Presidential Medal for Freedom. He knew many languages and his translation of Ibsen’s A Doll House was running on Broadway when Our Town opened. He wrote The Matchmaker, which had a long Broadway run, and its adapted version, Hello, Dolly, played even longer. He wrote a famous screenplay for Alfred Hitchcock, and his friends included both Sigmund Freud and Gertrude Stein. Even with all of these accomplishments, few of us would think to place him on our list of great American writers.
Theophilus North is set in 1926 and reads as if it is a slightly fictionalized version of the author’s life. In the summer of 1926, Theophilus, our narrator, a graduate of Yale, has left his teaching job at a prestigious prep school in New Jersey (Wilder had taught at Lawrenceville and graduated from Yale) and heads off to Newport, Rhode Island, near where Theophilus (and Wilder) had been stationed in World War I. Importing archeological ideas from ancient Troy, North tells us his theory of nine cities of Newport—early settlers, seaport, playground for the rich, local workers, and so on. North spends the summer teaching tennis to and tutoring youngsters and reading to the elderly. Each chapter is a short story, with some of the same characters popping up in many of them. Each story has a similar structure: A problem or a mystery crops up, and Theophilus resolves it. Although those helped are grateful, he always rejects pay or any hint of future consideration. The book explores the various posited Newport cities but does not have any central plot or moral or theme. Each chapter could stand on its own. This made for satisfactory, episodic reading. A chapter a day is the way I approached it.
As I was reading, I kept thinking that Theophilus North reminded me of something else that I had read at about the same time, but at first I could not place it. It was not the dissection of a time or place as in Updike’s Rabbit novels. It was not the intertwined short stories of Colum McCann’s Let the Great World Spin. Or a book like Elizabeth Strout’s Olive Kitteridge with vignettes of intersecting characters. It was not his contemporary or semi-contemporary authors writing about American themes, like O’Hara, Bellow, or DeLillo. Instead I realized it reminded me of another episodic book, The Second Rumpole Omnibus by John Mortimer, a collection containing three Rumpole books that had been separately published. Each Rumpole book consists of short stories, but, as with Theophilus North, characters recur and incidents from one story are referred to in another. The Rumpole stories are similar to Theophilus not only because of the first-person narration, but also because at the beginning of each story a problem or mystery is presented and by the end the situation is neatly resolved by the narrator. Both North and Rumpole, the well-worn barrister, have pockets of erudition; North has a vast knowledge of literature and languages; Rumpole knows bloodstains, Wordsworth, and judges. But given the choice, I would take Rumpole over North. Wilder has created a character that seems too good to be true, while one can imagine the true existence of Rumpole because, although an idealist, he is flawed. North is a prig; Horace Rumpole has self-deprecatory humor and a wife who at least slightly terrifies him (the infamous “She who must be obeyed”). I would like to have a glass or three of Chateau Fleet Street at Pomeroy’s with Rumpole because I might not only enjoy the conversation, but I also might learn something about human nature. I can’t imagine having a drink with North unless I wanted to learn more about him. I’m sure he would be delighted to tell me.
The New York Times in its book review interviews writers and asks them what writers, living or dead, they would like to have dinner with. No one is going to interview me for The New York Times Book Review, but I find that interesting to think about. If asked, I would like to get together with the fictional Ray Carney and Horace Rumpole. I think that they would find each other fascinating, but I would like it to be in a New York bar, or diner, or Chinese restaurant. For various reasons, I no longer live in New York, but Whitehead reminds me of how much the City has been part of my being. I miss it. I relate to the conclusion of Cool Machine when Carney is thinking about the next phase of his life and ruminates: “Escape from New York. The question remained: Where do you go? There was no place else. It was like going on the lam from yourself. He had been suckered before and fallen for scams. Swindled himself when he let vanity or pride get the best of him. Same as anyone. But he’d never been so foolish as to fall for that long con, the biggest con of all, that there were other places besides New York City.”
As Whitehead dedicates his most recent book: for New York Fuckin’ City.
