When I Was Puerto Rican chronicles Esmeralda Santiago's childhood in Puerto Rico and her family’s migration to New York City when she was thirteen. Esmeralda is four when the story begins, living with her parents, Ramona and Pablo, and two younger sisters. They live in Macún, a rural neighborhood in Puerto Rico, and Santiago vividly describes the wildness and picturesque beauty of her childhood home. Her parents suffer from marital conflict that impacts the entire family. Ramona is always striving for a better life; tiring of Pablo's infidelities, she moves the family to San Juan.
In San Juan, Esmeralda gets teased for her country accent and mannerisms. Ramona gives birth to another child, Alicia. Pablo and Ramona reconcile and they all go back to Macún in the country. Esmeralda’s parents fall into a pattern of fighting, separating, and making up. Each time, Ramona moves the family, creating a sense of instability. In their many homes, Esmeralda and her siblings must adapt to new neighborhoods, schools, household rules, and cultures.
Ramona finds work to complement Pablo's income, so the kids end up with the neighbor, Gloria. That all changes when Ramona gets criticized by their neighborhood for letting a neighbor raise her kids. At only twelve years old, Esmeralda becomes responsible for taking care of her six younger siblings. After the youngest, Raymond, seriously injures his foot, Ramona decides that they're moving again.
They move to a neighborhood in San Juan called El Mangle, but it’s hazardous, having been built above a lagoon contaminated with sewage. Raymond’s foot continues to get worse. Ramona is determined to find a solution and travels to New York for medical help. She returns inspired by the vibrant hustle of New York City, and with a sense of hope that a better life is possible. When Pablo finally refuses to marry Ramona, she decides to move the family to New York City.
The family flies to New York, where they connect with Esmeralda’s maternal grandmother, Tata, who has lived in the states for many years. The family faces various hardships: discrimination, financial instability, and the challenge of adapting to a new culture. Teachers underestimate Esmeralda due to her lack of English, however, she proves her intelligence and hard work ethic. Pablo remarries, and Ramona is happy with her new boyfriend, Francisco. Unfortunately, Francisco dies of cancer after their first child is born. In New York, Ramona relies on Esmeralda to help her translate. When Ramona loses her job, the two have to navigate the bureaucratic welfare system. A mentor encourages Esmeralda to try her hand at acting. Esmeralda auditions for the High School of Performing Arts, viewing it as her chance to escape her life in Brooklyn. In the epilogue, Esmeralda has successfully made it through the High School for Performing Arts and is finishing her degree at Harvard.
