PALOMA NEGRA, paloma negra!” Ana Castillo’s mother sang in Spanish in their Chicago home, “I don’t know whether to curse you or pray for you.” She sang the classic Mexican ranchera with her lovely voice again when Castillo left through the door at 19 in search of adulthood, a journey that would find her becoming an acclaimed Chicana author and a mother herself. Looking back at it all, Castillo reflects, in her newest collection of essays, Black Dove: Mamá, Mi’jo, and Me, on all three generations. She weaves childhood memories, like her mother’s singing, through her own struggles raising a son, including dealing with his time in prison, the hardest thing she’s ever had to write about.

Born to Mexican parents in working-class Chicago, Castillo originally thought of calling her latest book, “My Mother’s Mexico” after an essay she first wrote in 1993. “It was going to be more about being the daughter, later it became more about being a mother,” Castillo told me in a phone interview. “The most recent work — a good part of the book is brand new and unpublished — is about a single mother raising a young man of color, particularly in the city of Chicago.”

Through the pages of Black Dove, the rites of passage, and the relations between mother and daughter and mother and son are revealed to be not completely different. Castillo came of age in the late 1960s aware of the political tumult occurring all around her, including the historic 1968 clash between protesters and police in Chicago. “From my back porch we saw smoke rise up from tear gas set off during the Democratic National Convention,” she writes. But Castillo also faced a quiet riot raging from within, feeling very much the outsider, sometimes dealing with spells of catatonia.

“I think Black Dove’s title relates to the ‘Black Sheep,’ as we would say in English, is a person who we love and hasn’t always done the smartest thing, but we still embrace,” Castillo told me. “And I think my mother felt that way about me at the time.” Surrounded by prejudiced police, predatory men, and street gangs, Castillo found little in the way of refuge in Chicago. She dealt with the hostile world outside her door through her ever-increasing love of literature. By the time she turned 19, she left Chicago to study in Mexico, seeking out new cultural surroundings and developing the political consciousness that became more and more important to her emerging identity.

The memoir turns from her mother to her motherhood. She raised Marcello, her son, as a single mom in a Chicago decades after her own upbringing, but in an area still plagued by the same social problems. Police still stopped brown youth, like her son, for being brown, and gangs still roamed the streets. Castillo tried her best to raise Marcello in as much safety as she could provide in a world hostile to his existence. She took him on vacations to places like the Galápagos Islands, shared literature, and stressed the value of education and the arts. Marcello took up the cello in high school. Being a feminist, she also wanted to ensure he respected women, especially when he became romantically interested in them.

But Marcello battled a gripping alienation not that different from his mother’s own youthful experience. “One of the hardest things I had to accept was that there’s a world outside of the door of our home,” Castillo says. “I had to really look at this from his perspective to try and understand where the anger came from because he had a lot of pent up anger at society.” Hip-hop and graffiti writing became his outlet, but Marcello largely stayed out of trouble, graduated from college, worked, and started a family.

Everything seemed fine until Marcello got arrested for robbery on a December day in 2009. “I was in great shock when I learned of my son’s arrest, because he didn’t have any history,” Castillo said to me. “In the process of my shock, initially I couldn’t even write about it, even in my journal, which I’ve kept for decades. I couldn’t even write it to myself, what had just transpired. It took some time.” What helped bring Castillo out of that stunned state were emails she exchanged with her son — some included in Black Dove — over the course of his two-year imprisonment. They talked about books they read together and discussed ideas about the world. It seemed to revive a sense of purpose in Marcello, lifting him out of his own pangs of depression. “Originally, he almost seemed like a stranger to me,” Castillo said. “But he became more and more present.”

When Marcello got released in 2014, Castillo wrote Give It To Me — a comic novel that provided airy relief for the author and readers alike. A year later, she finally readied herself to express what had gone on in those dark and fearful days. Castillo wondered if it would be cathartic to write about such a painful experience. A teacher of memoir writing, the time to walk her talk had come. Firmly established, Castillo left major publishers and teamed with The Feminist Press, whose editor suggested she read The New Jim Crow by Michelle Alexander, about mass incarceration in the United States. “It helped me enormously to help me sift what was going on personally with what was going on in a bigger world,” Castillo says.

In writing Black Dove, Castillo comes to terms with her mothering. Some people, including family members, had tried to put the blame on her for Marcello’s incarceration, claiming it was because she had tried to raise a boy without a man in the house. But, she said, her son told her “that I was a great mom and has not blamed me for his decisions.” After leaving prison behind, Marcello is now working toward a career in law.

Castillo writes, in the introduction to Black Dove, that some readers perhaps will feel like her stories have nothing to do with their lives, but to me they felt deeply intimate. The same Chicago street gang she names during both her and Marcello’s upbringing branched out to Anaheim and had a strong presence while I was coming of age there. Castillo dedicates another essay to her home along the Mexican border far removed from Chicago. The same Franklin Mountains that she views from her vantage point in southern New Mexico have formed the backdrop of many of my childhood memories visiting my grandmother in El Paso, Texas.

While I’m close to Marcello in age enough for his struggles to be relatable, the real power of Black Dove comes when it speaks to what mothers face raising black and brown children all across this nation. Castillo hopes they come away with affirmation and understanding in a world full of mother-shaming. “As long as they know in their hearts they are doing their best every day and whatever time allows for them to be more involved in their children’s lives is time well spent,” Castillo said to me. “In the end, our children are not as much an extension of ourselves as we would like to think.”

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Gabriel San Roman is the author of Venceremos: Victor Jara and the New Chilean Song Movement, co-creator of the 2016 Calendar of Revolt, and a writer with OC Weekly.