The Bailey brothers’ mother, Milagros, immigrated to their unnamed New York borough from Puerto Rico. The decades after the end of World War II brought an influx of immigrants from Puerto Rico to New York City because of a joint effort by the United States and Puerto Rican governments to satisfy the labor shortage in the US following the war. Meanwhile, the Puerto Rican government could not support its growing population. Historically, Puerto Rico was an agrarian-based economy, but after focusing too heavily on the single crop of sugar cane, its economy suffered. As the 1950s approached, its government sought to shift from a farming-based economy to an industrial one. The plan, termed Operation Bootstrap, sought to address both nations’ dilemmas by encouraging Puerto Rican immigration to the US.

While some Puerto Ricans migrated to the American Midwest, where farming jobs were available, the majority went to the Northeast. Eighty-five percent of these Puerto Ricans immigrants settled in New York City and the areas immediately surrounding it. In the 20-year period following World War II, the Puerto Rican population of this area expanded from 70,000 to nearly 900,000 people (Román, Iván. “Why Puerto Rican Migration to the United States Boomed after 1945.