Breach of Covenant, Queens-style

Colson Whitehead’s “Cool Machine”: The Envelope Is the Consideration

Cover of Colson Whitehead's "Cool Machine" at a bookstore

Colson Whitehead | Cool Machine: A Novel (Harlem Trilogy | Doubleday (368 pages)

Every contract requires consideration. In 1980s Queens, it apparently required an envelope full of cash.

Two-time Pulitzer Winner Colson Whitehead did not phone it in when he was writing Cool Machine. Whitehead has spent much of his career writing novels like The Underground Railroad and The Nickel Boys that confront America’s darkest history. The Harlem Trilogy occupies different territory. These are historical thrillers populated by furniture dealers, fences, lawyers, politicians, developers, artists, mobsters, and one unforgettable sociopath named Pepper.

Cool Machine is a beautifully plotted, fast-paced novel. The best of the Harlem Trilogy and a genuine best-of-the-year contender. You don’t need to know anything about Donald Manes, the Board of Estimate, or municipal contracting to enjoy it (but it helps). If you like mysteries, literary fiction, or New York history, read it. If you read exactly one novel this year, make it this one.

No Radios

A great pleasure of the book is revisiting dirty, old New York. As someone who arrived in New York in 1979, I found myself admiring Whitehead’s rendering of the city: “WORSHIP GOD” scratched into every payphone booth, a Gray’s Papaya hot dog (still there) next to a now-cleaned-up Needle Park, and “No Radios” signs propped in car windows to ward off break-ins. Downtown Beirut in Alphabet City! I have not thought about that place in decades. Whitehead was only sixteen in 1986. This is research, but it reads like memory. No notes.

Terms and Conditions

First, the setup. Ray Carney, the respectable owner of Sterling Furniture, contemplates one last score when the banks refuse to finance his wife Elizabeth’s travel agency. Meanwhile Pepper, his old partner in crime, drifts through the downtown art scene, where violence inevitably finds him again. Twenty years after his cousin Freddie’s death, Carney gets one last chance to save Freddie’s son from repeating the family’s history. There are robberies, betrayals, and unforgettable supporting characters.

My focus, though, is narrower. One of the novel’s central threads is based on the spectacular real-life corruption scandal that consumed New York’s headlines in 1986. Whitehead follows the Donald Manes story remarkably closely without ever feeling trapped by history.

Donald Manes, the Queens borough president and captain of the county Democratic Party, wielded power that rivaled Tammany Hall in its heyday. Sitting on the all-powerful Board of Estimate, he controlled patronage jobs, public works projects, and municipal contracts across the borough. As Whitehead writes, Manes had a hand in everything on the street, from the Taxi and Limousine Commission to commercial zoning and subway shelters, and everything below it, from gas lines to sewer maintenance and miles of water mains. “The King of Queens,” he called himself.

How do you translate a massive, multi-million-dollar municipal monster into an intimate human story? You bring in the lawyers. Henry Pierce, a young civil rights lawyer, sums up the entire scandal for Carney over lunch at Empire Szechuan early in the novel in five words:

“It’s the same old story.”

Whitehead spends the rest of the book proving him right.

In a lesser writer’s hands, what follows would be pages of eyes-glaze-over exposition. Instead, Henry becomes one of the novel’s most entertaining supporting characters, beginning with his downtown tailoring (a double-breasted power suit, tie slashed with aggressive stripes). Step by step, he peels back the layers of the Manes machine, delivering one funny, cynical observation after another until everything snaps into focus:

  • “The Manes indictment pulled off the scab. Here’s the man who might be our next mayor, and he’s running a top-flight extortion network plugged in to multiple city agencies. You want to build a housing complex? You have to pay Donny. Build a shopping mall, maintenance contract? Do any business with the city? It’s all Donny Manes and the Board of Estimate.”
  • “The city made tens of millions of dollars each year off parking tickets, and if you wanted that contract for your collection agency, you gave an envelope every month to one of Manes’s bagmen at the Parking Violations Bureau.”
  • “The details and names of the actors were new, but at its heart it was a simple envelope story. Who was reaching into their pocket and who had their hand out.”
  • “The whole machine of bribery, which is really what makes this city run, is up for grabs.”

Carney has already absorbed months of tabloid coverage. He’d assumed Manes was crooked in some vague way, because all politicians were crooked, and as Mayor Koch’s right-hand man there was no shortage of opportunity. Henry fills in the missing pieces, right down to a company called CitySource, which lands a $22 million contract for a portable computer that exists only on paper. The diagrams exist. The patents exist. The machine itself does not.

It’s Carney that gets the last word: “Someone should get a contract for making a computer that keeps track of envelopes of cash.”

Colson Whitehead already has. In that single, cynical line, he distills an astonishingly complicated municipal corruption case into one perfect observation: the envelopes are the contracts.

Building block by building block, he turns what could have been a bewildering civics lesson into the clearest explanation of political corruption I’ve read in a novel.

Whitehead also recreates, almost scene for scene, the astonishing opening of Manes’s downfall. Police stop his car on the Grand Central Parkway. The borough president is bleeding from a slashed wrist. He claims two mysterious men forced him to injure himself. Mayor Ed Koch urges New Yorkers to stay away from liquid diets. The tabloids have other ideas. Whitehead changes remarkably little because he doesn’t have to. The real scandal was already stranger and better plotted than fiction usually allows.

There is much more going on here than envelopes. This book is about family, race, loyalty, ambition, aging, and the bargains people make with themselves over decades. Pepper remains one of the great supporting characters in contemporary fiction. Ray Carney remains one of its most memorable protagonists. The Harlem Trilogy ends the way it began: funny, humane, thrilling, and deeply observed.

I just happen to think the envelopes explain the whole machine.


Thanks to Doubleday and NetGalley for the ARC.