1898, the U.S. Occupation

Spain ceded Puerto Rico to the U.S. at the conclusion of the Spanish-American War in 1898. This shift ushered in profound political, economic, and social transformations that continue to shape Puerto Rican life today. Early U.S. rule included a military government and economic restructuring that created ongoing dependence on imported goods. Puerto Ricans were granted U.S. citizenship in 1917, and the territory became a U.S. Commonwealth in 1952, with limited self-government.

 

The Stereograph

Stereographs were a popular late nineteenth-century photographic process in which two nearly identical images were viewed together through a stereoscope, producing a three-dimensional effect. Widely circulated for popular entertainment and education, they enabled audiences to collect and experience images of distant places from the comfort of their own homes. After the Spanish-American War of 1898, stereographs often depicted staged representations of U.S. military exploits, landscapes, and local communities, accompanied by titles and descriptive text that shaped how viewers understood newly acquired territories such as Puerto Rico.

 

Infantilization and Categorization of Colonial Subjects

After 1898, Puerto Ricans were portrayed in U.S. popular media—from stereographs to newspapers and magazines—as new colonial subjects or “natives,” categorized through racialized, class-based, and gendered frameworks. One recurring image was that of impoverished Puerto Rican children, or of the island itself personified as a child in political cartoons. These images reflected a broader American imperial discourse that cast Puerto Rico as childlike, ignorant, and dependent, helping justify U.S. military intervention and long-term control of the island as necessary and benevolent.

 

Hurricanes and Natural Disasters

Natural disasters are a recurring part of Caribbean life, marked by cycles of devastation and recovery. In Puerto Rico, hurricanes have inspired artistic and cultural expressions—from painting to song—that reflect both loss and resilience. In 2017, Hurricane Maria made landfall as a powerful Category 4 storm, causing devastating loss of life and exposing failed infrastructure after decades of neglect. Botched recovery efforts triggered a humanitarian crisis and a major new wave of migration, marking a significant new chapter in Puerto Rico’s diaspora to the United States.

 

Military Presence

Colonial military might has shaped Puerto Rico’s history from Columbus’ arrival in 1493 to the present. Castillo San Felipe del Morro, built by the Spanish, is one of the largest fortresses in the Americas. Puerto Rico’s strategic location made it a U.S. military asset during the 20^th and 21^st Centuries. The island municipalities of Vieques and Culebra were used for naval exercises and bombing practice despite risks to local residents and the environment. In 2026, military bases in Aguadilla and Ceiba served as launching points for operations in Venezuela. Since 1917, Puerto Ricans have served in the U.S. military, most notably in the 65^th Infantry Regiment, a segregated, all-Hispanic unit honored by several public monuments, including one in New Britain, CT.

 

Indigeneity and Taíno Heritage

Before colonization, Borinquen / Borikén (Puerto Rico) was the ancestral home to the Taíno and other Indigenous groups. Following the arrival of the Spanish, these communities suffered devastating population loss through enslavement, violence, and disease. Taíno material culture, music and language inform Puerto Rican heritage, along with that of enslaved Africans and 20^th Century U.S. popular culture. These complex, interwoven, and sometimes contradictory elements form the basis of the living intersection at the core of Puerto Rican identity today. From a Hartford street mural to the pastry boxes used by a New Britain bakery, the ongoing visibility of Taíno imagery highlights how Puerto Rican communities acknowledge their Indigenous heritage.

 

Concepts of Race

Puerto Rican society was racially stratified during Spanish colonial rule, but the arrival of U.S. forces (with many soldiers and officials from Southern states) brought a new, more malicious emphasis on race. This is methodically reflected in official U.S. discourse and photography. The condescension extended even to “The Porto Rican whites.” Puerto Rican racial identity has often been understood through the concept of the Puerto Rican family, which emphasizes an idealized vision of harmony among European, Indigenous, and African communities. Contemporary scholars have critiqued this cultural ideal for overlooking unequal social realities and the experiences of historically marginalized groups.

 

The Coconut in the Puerto Rican Imaginary

Coconuts may be emblematic of the Caribbean, but they are not a native plant to the region. Originating in Asia, they were introduced through European colonial trade. They provide a source of physical and economic sustenance. Coconuts are a key ingredient in local gastronomy as well as in “exotic” umbrella cocktails consumed by tourists. The coco frío, or cold coconut with a straw, is a favorite refreshment and also a common prop used by wealthy elites and politicians in press photos.

 

Waiting

Waiting exposes the limits of institutions, where quick solutions are often impossible. For decades, Puerto Ricans have waited in lines—both literal and symbolic. During World War II, they lined up to enlist in the U.S. military, serving a country that often treated them as outsiders despite their citizenship. On payday at the sugar plantations and at the factories, men and women waited for their meager wages, much lower than comparable wages in the continental U.S. After Hurricane Maria, families waited for hours for gasoline and water, or for flights out of the island. Across generations, these lines have embodied expectations, struggles, and community solidarity.

 

The Diaspora

A pursuit of opportunity and security has driven migration from Puerto Rico to the continental United States. Large waves of migration followed World War II, promoted by the local government, aided by Pan American and Eastern Airlines, and supported by labor contracts in industries such as Connecticut’s shade tobacco. More recently, the widespread infrastructure damage and humanitarian crisis caused by Hurricane Maria prompted relocation to mainland cities such as Hartford and New Britain. Today, more Puerto Ricans live in the diaspora than on the island.

 

Women: Sterilization and the Pill

After the U.S. occupation of Puerto Rico in 1898, high birth rates were increasingly framed by policymakers as a social “problem,” often linked to poverty and illiteracy. Beginning in the 1930s, particularly after the passage of Puerto Rico’s Eugenics Law in 1937, tens of thousands of women were sterilized without full informed consent, often under economic or institutional pressure. By the 1960s, an estimated one-third of women of childbearing age had undergone the procedure. Between 1956 and 1957, Puerto Rico was also selected for early large-scale trials of the birth control pill, conducted without adequate disclosure of risks or side effects.

 

The Debt and PROMESA

The elimination in the late 20^th Century of favorable tax laws that attracted industry to Puerto Rico led to the closure of factories and significant job losses. The territory consequently amassed a huge debt. In 2015, the governor declared the debt unpayable, prompting Washington to impose a fiscal oversight board to orchestrate debt repayment. Known as “La Junta,” this oft-reviled entity holds power over and above any locally elected official. The resulting austerity and privatization measures skyrocketed the cost of living, led to the closure of hundreds of schools, cut pensions for retired workers, and eliminated critical services, promoting further population exodus.

  

Tourism

Puerto Rico’s natural beauty draws millions of tourists each year, particularly from the continental United States, because U.S. citizens do not need a passport to visit. Long promoted by the government as a development strategy, tourism has generated economic activity but has also significantly affected the quality of life and well-being of Puerto Rico’s residents. The rapid expansion of short-term rentals has displaced long-standing communities and contributed to a severe shortage of affordable housing for low- and middle-income residents. While many visitors are respectful and well-intentioned, tourism often places workers in unequal relationships that require emotional deference and service to visitors whose leisure is prioritized over local needs.

 

Housing and Land Use

During the shift toward industrial development in the 1950s, people from across the island relocated to urban centers in search of work. Highway construction facilitated mobility and reshaped the landscape. Dilapidated city slums gave way to caseríos—public housing developments initially promoted as safe, temporary solutions for low-income and working-class communities. At the same time, private suburban housing developments, or urbanizaciones, dotted with identical single-family homes, were built for the emerging middle and professional classes, further reinforcing spatial and economic divisions. A sense of nostalgia remains for the old, rural way of life and its rustic casitas, even as much housing stock today sits in ruins.

 

Police Surveillance

In the mid-20th Century, the Puerto Rico Police, in close coordination with the FBI, maintained a wide-reaching surveillance program to monitor, photograph, film, and wiretap individuals suspected of supporting or sympathizing with organizations or political parties advocating for Puerto Rican independence. Approximately 135,000 people were surveilled. In 1987, the surveillance was declared unconstitutional, and in 1992, targeted individuals were permitted to retrieve their unredacted files. In 1978, Puerto Rico Police also orchestrated the ambush and execution of two young independence activists at a communications tower on a mountain top in central Puerto Rico known as Cerro Maravilla.

 

Connecticut and Los Macheteros

In 1983, a group known as Los Macheteros (the cane cutters) or The Boricua Popular Army carried out what was then the largest cash robbery in U.S. history at the Wells Fargo armored truck depot in West Hartford, Connecticut. Victor Gerena, the “inside man,” escaped with approximately 7 million dollars, allegedly intended to support Puerto Rican independence efforts. Filiberto Ojeda Ríos, a founder of Los Macheteros, was tried in absentia in Hartford federal court and convicted of conspiracy and bank robbery. In 2005, he was assassinated by the FBI in Puerto Rico. Victor Gerena remains at large, and the money was never recovered.

 

Modernization and Operation Bootstrap

Beginning in the late 1940s, Operation Bootstrap was an economic program designed to shift Puerto Rico from an agricultural to an industrial economy by attracting U.S. manufacturers through tax exemptions and low labor costs. The program improved the quality of life for many, but it also dramatically reshaped the island’s social and physical landscape. Puerto Ricans moved from rural areas to cities to work in factories, accelerating the decline of agricultural labor, while others migrated to the United States through organized labor recruitment programs. As manufacturing—and later the pharmaceutical industry—expanded, a new Puerto Rican middle class emerged.

 

Resistance and the Struggle for Self Determination

The Puerto Rican push for independence dates to Spanish colonial times, with prominent figures such as Ramón Emeterio Betances and Segundo Ruiz Belvis leading the struggle. Under U.S. rule, the pursuit of independence took both peaceful and violent forms. Puerto Rico’s Law 52 of 1948 (the “Gag Law”) criminalized the expression or publication of nationalist ideas. A 1950 revolutionary uprising was put down by the Puerto Rico National Guard and U.S. infantry troops, who bombed the towns of Jayuya and Utuado, with fatalities on both sides. Many insurrectionists were captured. In 1954, nationalists, including Lolita Lebrón, opened fire in the U.S. House of Representatives to protest colonial rule. During the 2024 gubernatorial election, Juan Dalmau, the pro-independence candidate, came in second with 31% of the vote.

 

Social Class and the Elites

Despite the creation of a new middle class, mid- to late-20th-Century transformations in Puerto Rico highlighted social inequality between the island's elites and working-class communities. Historically, the island's elites have been the primary mediators in Puerto Rico’s dealings with the U.S., often securing privileges and opportunities out of reach for most. Meanwhile, many of the less privileged worked in service sectors, such as tourism, often encountering visitors in subordinate roles. The 2019 protests that led to Governor Ricardo Rosselló’s resignation were partly sparked by leaked private messages in which government insiders and elites mocked victims of the recent and devastating Hurricane Maria and marginalized communities, exposing the island’s continued social and economic divisions.

 

The Flag and the two Flags

When Puerto Rico officially became a U.S. Commonwealth in 1952, public buildings were required by law to display both the U.S. and Puerto Rican flags, a pairing that represented the newly reconfigured political relationship. The Puerto Rican flag has always evoked island pride, but it also has a long, complex and contested history. Various versions are in use today, each with different symbolic meanings. The flag was designed by Puerto Rican independence advocates in New York in the late 19^th Century and was based on the Cuban flag. Its design is widely commodified and reproduced on everything from clothing to bumper stickers. It is recognized worldwide, in cities such as San Juan, Hartford, Madrid, and Hong Kong, as an affirmation of Puerto Rican identity and culture.

 

School for Maids

During the mid-20th Century, migrant labor conditions among Puerto Ricans in the United States followed gendered patterns. While many men found work in agriculture, women predominantly entered domestic work, taking jobs as laundresses, maids, and seamstresses, often in low-wage, informal settings. In 1948, convinced the island was overcrowded, the Puerto Rican government established a “School for Maids” in the city of Caguas to train women for domestic service in wealthy homes on the East Coast of the United States. Before beginning their stateside employment, the women were taught to navigate the norms of the American household, including cooking and answering the telephone.

 

English Language Instruction

After the U.S. took control of Puerto Rico in 1898, authorities implemented a policy of Americanization aimed at transforming and “civilizing” Puerto Rican society. One example was the 1902 imposition of English as the mandated language of instruction in public schools, despite the fact that most knew no English. This initiative failed. After decades, Spanish was finally declared the language of public instruction in 1949, with English taught as a second language. Spanish remains the most widely spoken language, with English used in U.S. enclaves and tourist areas, in some official documents, and by some diasporic Puerto Ricans who have returned.

 

Connecticut Diaspora

Puerto Ricans have made Connecticut their home since the mid-19th Century. After World War II, migration to the U.S. mainland expanded, and the state became an important—though historically overlooked—site of the diaspora, alongside cities like New York and Chicago. Beginning in the 1950s, labor recruitment programs brought Puerto Rican workers to the Connecticut River Valley to meet demand in the shade tobacco industry. Many initially arrived as seasonal farm workers but later settled permanently, helping sustain key industries while building enduring communities. Today, nearly 300,000 people of Puerto Rican heritage live in Connecticut. In New Britain, Puerto Rican labor and civic contributions are commemorated through community institutions, annual parades, the Borinqueneers Memorial, and in personal style, as seen in the t-shirt on display, featuring the Puerto Rican and American flags atop the text Hartford, Connecticut.