Around her hometown of Jackson, Tennessee, Avery Cunningham was known as “Doctor Cunningham’s daughter,” or sometimes “Cheryl’s daughter.” Avery’s move from that small, insular Southern town to Chicago gave her the proper distance to forge her own identity. She began her college studies at DePaul University in 2011. She was eighteen years old, ambitious and possessed of a deference and formal politeness uncommon amongst her classmates. She called her elders “Mr.” or “Mrs.,” “Sir” or “Mam.” Over the next five years, Cunningham excelled. She worked her way through a combined degree program, took on internships, volunteered as editor at literary journals and community newspapers, and served in various capacities at arts organizations. In 2015, she earned her BA in English with a literary concentration; a year later she completed a master’s in writing and publishing. Not long after that, she was on her way back to the Memphis area.
“Chicago really allowed me to have more agency over my own life, my own experience, to be more comfortable, more confident, to challenge myself, to stand out on my own merit,” Cunningham says. “Whoever I am now, truly began at DePaul University—the friends I made there, the mentors I made there, had a very profound impact on me.”
Cunningham’s debut novel, “The Mayor of Maxwell Street,” is an historical novel involving a Southern Black family’s “season” in 1921 Chicago. It’s a sweeping, twisting, complex story that grounds its big ideas in a Chicago as much murderous as it is marvelous.
“Season” is a fancy term used by wealthy people. Think Jane Austen’s world. Indeed, the ballrooms of Cunningham’s novel rival those of any Victorian romance. That this grandeur belongs to Black people should not be surprising, but as a literary depiction it’s rare.
Cunningham’s novel deftly shows that there are many facets to the Black experience. The daughter of a cardiologist father and teacher-entrepreneur mother, Cunningham grew up in prosperity. In plotting “The Mayor of Maxwell Street,” Cunningham knew she wanted to defy the usual media depictions of Black people in distress. She says she “wanted to explore all of the complexities of that Black high society—colorism, classicism, internal biases, conflict between academic and nouveau riche spheres of influence.” This exploration does not in any way deny social injustice, but frames it in a different way, with different manifestations.
And Cunningham’s novel certainly makes a bunch of hard turns away from that proper, glittery society—into Chicago’s alleyways and underground clubs and mythical bazaars. The author’s heroine, on assignment with The Defender, introduces us to all manner of Chicago’s people and places as she chases down a dangerous but important story.
Your novel takes place in Chicago, circa 1921. Before we get into our discussion of everything else, I’d like to hear about your interest in that historical moment. There is so much happening in Chicago then, and it’s not all flappers and bootleggers, is it?
No, most certainly not! In fact, the scope of all that was changing in Chicago during this time could be viewed as a reflection of all that was happening in the United States. The strict class, gender and moral confines that existed before World War I were being challenged, along with some racial confines. This was a time of freedom and self-esteem, but also terrible violence and corruption. Chicago was a place where anyone and everyone—from immigrants fleeing the Old World to Black Americans fleeing the South—could come to pursue the American Dream. For a writer, this is fertile ground for the types of stories I like to tell: where the duties and responsibilities that drive us conflict with the ambitions and passions that inspire us.
It’s your first novel. Like a lot of debut novelists you are bursting with big ideas. For now, tell me why this notion of being at once “within and without” is so important to you and to this book.
On a kind of superficial level, this idea is what ties my debut to its initial inspiration, “The Great Gatsby”: “I was within and without, simultaneously enchanted and repelled by the inexhaustible variety of life.” On a more personal level, this idea of being a part of something—a group, a class, a culture, a community—while at once being confused by it, or even exiled by it, is one I’ve lived with my entire life.
I was lovingly raised in a small Black community in West Tennessee. And yet—mainly due to my parents’ brutal divorce and the battle lines it drew—it was not my community. I viewed it through a thick pane of glass where I could see everything, but fully experience nothing. All of the characters in “The Mayor of Maxwell Street” confront this feeling in very grand and very intimate ways that often move them to make damning decisions.
The Sawyer family is the richest Black family in the country, at least by some accounts. They are Kentucky horse breeders who’ve seemingly made their fortune in ways both respectable and admirable. Jay Shorey comes from an indeterminate family background and presumably makes his money in ways both disreputable and illegal. Almost from the instant this story begins, these two worlds intersect: high society and the underworld. On the surface, they are very different landscapes populated by very different characters. On closer examination, they have much in common?
Yes, exactly. At the root, both of these worlds are represented by Black characters. They both have moments where they realize that respectable or disreputable, the prejudiced mindset that runs through America like lifeblood will judge them either way.
That tragic irony is an essential part of the Black experience, and one that we can view directly play out in Nelly and Jay’s dynamic. They both come to learn—in one way or another—that wealth will not save them. The right clothes, or the right name, or the right lifestyle, or the right ambition will not save them. The change that is needed is bigger than their individual aspirations; one of them takes this lesson to heart. The other does not. It is up for the reader to decide which one made the “right” decision.
This is, in part, a story of Black culture at the height of the Great Migration. It is, contrary to many popular depictions, a story of the upper echelons of Black culture. Like wealthy white society, this wealthy Black society is comprised of every manner of social climber, from genius businesspeople to violent gangsters. But there is a distinct difference between Black and white rich society at this juncture in American history. Talk a bit about those distinctions.
The greatest distinction is that Black high society is still exposed to racism. Jim Crow is at its height during this period, and the ability to distance one’s self from the injustices across the country becomes ever more difficult to manage. This made some communities in Black high society rather covetous of their positions, and dismissive of Black Americans who don’t fit into the mold that respectability politics demanded.
That brings us to Penelope Sawyer, affectionately known as Nelly. The daughter of the affluent Ambrose and Florence Sawyer, Nelly had remained “properly invisible” until her older brother Elder’s tragic, early death. Now, she is in the spotlight. It’s not enough for her to be admired for her wealth or even her beauty. Her parents want nothing more than for Nelly to attract a suitor who will enhance the family’s status and secure a kind of generational place amongst the most influential Black Americans. Nelly wants more. What, at the core, is Nelly after, and how did you use Nelly to get at your own exploration of ambition, pride and respect?
Nelly is after what, I think, many young people raised in relative peace and privilege are after. To be known and respected based on her own merits instead of the merits she inherits. Because of who her parents are, she has never been called on to prove herself, and that challenge is something she craves. However, even though she heedlessly pursues an arena to test her mettle, she knows that she will never be without a safety net. She resents this security as much as she clings to it. It is not until the very last pages of the novel that Nelly learns to take pride in what she has, and in what she can build upon. That her ambition feeds a legacy, not just her own competencies. It is Nelly’s journey to go after her goals only to question the sincerity of them in the end. This is another point of contention between her and Jay. He often criticizes her for exposing herself to harm, danger, and even death to achieve something that he believes she already has.
The title derives from an unseen character in the story. The Mayor of Maxwell Street is a “shadowy figure.” He is rarely, if ever, seen. Nobody knows where he lives. Nobody knows his background. And yet he is Chicago’s most powerful broker, a liaison between all the criminal, political, corporate and judicial kingpins making the city beneath the city operate. Who is he? Tell us about this plot device and whether you consider your novel to be a mystery.
I think in some way all novels must be mysteries. It makes for a more compelling story. However, in this case, I cannot wholly say that “The Mayor of Maxwell Street” is a mystery. Mainly because it’s not the reader’s journey of discovery that is important, but Nelly’s. How does she go about learning who the Mayor of Maxwell Street is? What does the process teach her about her own instincts and the instincts of others? This is Nelly’s riddle to solve, and I feel the plot hinges on her experience even more than the audience’s.
It’s also a love story. Nelly is a debutante. She, rather against her own wishes, is coming out as a potential bride. Despite her reluctance to engage in these lavish, elaborate matchmaking efforts, Nelly does find love—not once, but twice. The love triangle between Nelly, Jay, and the dashing Tomás sets up an examination of worth. On the one hand, Jay embodies all the dirt and messiness and violence of a man born into poverty. On the other hand, Tomás represents the glitter and orderliness and culture of a man born into wealth. One is rough, the other gentle. One is abrupt, the other patient. And so on. To the outside world, the choice is simple. To Nelly, it’s complicated. Why?
The choice—if it can even be called that—between Tomás and Jay is a complicated one because both young men see Nelly for who she could be, not for who she is. Jay wants her to be someone willing to risk everything to achieve their goals, like him. While Tomás wants her to be a shining example of all the good that can be done by people blessed with wealth and position, like him. She loves Jay and Tomás for how they support her, motivate her, inspire her. But she also knows that what she wants out of romance is something neither of them will ever be able to offer.
Your novel does not scream “Disney.” I understand the idea for the book was purchased based on a proposal your agent sent Disney’s imprint, Hyperion Avenue Books. Within ten months—based on that initial synopsis, outline and two chapters—you’d brought this unexpected project to fruition. As you approach your publication day, share your thoughts on Hyperion Avenue Books.
I suppose you’d call this a Disney-adjacent property. What I enjoyed about working with Hyperion is that it’s a fresh new imprint. This is only its second class of books. They are still in the process of figuring out what kind of imprint they want to be. I was excited to be on the ground floor of something like that. They are still proving themselves, so I never felt like I was just part of a roster of names and IPs; I felt like everybody on the team very much believed in this project.
This is a major success, especially for an author so young. You should be proud of what you’ve accomplished.
I’ve never written anything that fast in my life. It was a trial and a tribulation. I felt like I was speaking to my generation with these characters, even though they are of their own time. These are very much conversations we’re having now, about having and finding peace while still facing all the systemic issues that exist. I enjoyed writing about Chicago. I enjoyed learning about its history, its structure, its demographics, its story. I hope it’s an homage to the city and the impact it’s had on me.
“The Mayor of Maxwell Street” launches on January 30 with a book event in Memphis. Cunningham returns to DePaul University on February 22 as part of the Visiting Writers Series. This interview was conducted over a series of email exchanges and phone calls, then edited for clarity.
“The Mayor of Maxwell Street”
By Avery Cunningham
Disney Publishing Group/Hyperion Avenue Books, 528 pages
Donald G. Evans is the author of a novel and story collection, as well as the editor of two anthologies of Chicago literature, most recently “Wherever I’m At: An Anthology of Chicago Poetry.” He is the Founding Executive Director of the Chicago Literary Hall of Fame.