Under observation 

In James Jennings’ “Wings of Red,” his storytelling is vulnerable and strong at the same time. 


“What else?” James W. Jennings asks in the opening paragraph of his debut novel, which is based on his experience as a substitute teacher in the New York City school system, as a writer and an artist, as a Black man who rides the city’s subways at night because he is unable to pay his rent. What else, indeed.

“Wings of Red” (Soft Skull) is the story of June Papers, a young man with an M.F.A. and a felony record, who reveals his story in real time through interior monologue, journaling, observations, and snippets of conversations. June writes in his journal, “Against all good advice, my life and my literature are inseparable.”

Jennings, who now lives on the Vineyard full-time and has worked as a teacher at both the regional high school and the Charter School, was living in New York and working for the New York City school system when he was writing “Wings.” The novel is a lightly fictionalized — the publicity materials for the book call it autofiction — account of his own story. “I would say, 99 percent of it is very real. The part of it that is fictitious is really the craftsmanship of it,” Jennings said in a recent phone interview.

The novel begins with June relating the situation he finds himself in. He’s unable to pay his rent, and is preparing for the inevitable. “Me being homeless is merely comedy until it dawns on me, listening to my own footsteps, that I’ve fallen for the pretty girl who can’t have whoever she wants.”

June is also writing a novel. And while this book deals with family, race, ambition, desire, and place, it is also about writing, and Jennings’ writing about writing is worth noting. “Writers are like clumsy robbers or career criminals with the poetics. What can feel like a successful finesse or a caper will inevitably evoke into the realization that we’ve been leaving behind clues to our entombment all along — pieces of a bigger picture that will eventually put us behind bars. Pieces that will become absolutely transparent no matter how wise or clever we are. All fiction inevitably reveals the truth.”

June couch-surfs when he can, and rides the subways between substitute teaching gigs, always writing: “I hear sentences come forth and link up into paragraphs every few blocks. I can see them illuminated like sky-blue neons in front of me.”

He also travels back and forth to the Vineyard, where his grandmother, who is dealing with significant health issues, lives, and where he feels truly at home. The authenticity of Jennings’ voice and his clear knowledge of what and where he writes — whether it be the exchanges he has with students, conversations with friends, the complicated family issues, his time in New York, on the Vineyard, and on the bus that gets him from the city to Woods Hole — allows readers to truly enter his world. It is the details, and his observations, that make the writing feel like you are looking at what he is seeing, rather than trying to envision what he’s describing. About the East Chop, he writes, “The Highlands smell like dirt, salt, and trees. White folks call the Highlands East Chop. We call it the Highlands. The history is different.”

And moving out of his apartment in the city: “Carry bedroom trash out front with the rest of our soaked belongings, and watch a litter of street kittens wrestling in the vacant lot.”

Jennings keeps detailed journals. “I become maniacal about documenting my experience,” he admits. His process involves not just putting pen to paper and fingers to keypad; he also records his writing, to hear how it sounds. “I write it out,” he explained. “And then I read it aloud to myself and I record that, and I listened to that, because I come from a history of a tradition of storytellers, and it’s very important to me to be able to communicate the story to not just people who care about literature but also to a 12-year-old, and to people who care less about literature.”

About writing “Wings of Red,” he said, “It was literally helping me survive. You start thinking things about yourself when you don’t have a place to sleep at night that aren’t too wonderful.”


“Wings of Red” is available at Edgartown Books and Bunch of Grapes. James W. Jennings will be speaking about the book at Pathways on Nov. 21 at 7:30 pm.