As of the 2010 census, Holyoke, Massachusetts had the largest Puerto Rican population, per capita, of any city in the United States outside Puerto Rico proper, with 47.7% or 44,826 residents being of Puerto Rican heritage, comprising 92.4% of all Latinos in the community. From a combination of farming programs instituted by the US Department of Labor after World War II, and the housing and mills that characterized Holyoke prior to deindustrialization, Puerto Ricans began settling in the city in the mid-1950s, with many arriving during the wave of Puerto Rican migration to the Northeastern United States in the 1980s. A combination of white flight as former generations of mill workers left the city, and a sustained influx of migrants in subsequent generations transformed the demographic from a minority of about 13% of the population in 1980, to the largest single demographic by ancestry in a span of three decades.

In time the city has become a center of Puerto Rican culture on the mainland, with at least one member of the Senate of Puerto Rico being an alumnus of Holyoke Community College, and the city being honored by both the Puerto Rican Cultural Center in the Chicago, and in New York City's National Puerto Rican Day Parade.

History Colonialism and early cultural exchange Following the passage of the Foraker Act, a United States designated colonial government was formed, as the island had been annexed by the Americans following the Spanish–American War. Soon after this government was instituted, several delegations were sent from Puerto Rico to various cities in the United States that were seen as potential trading partners on the mainland. Among the first of these delegations of legislature members and trade representatives, was one which would visit Springfield in 1901. In the following year the newly formed Puerto Rican government would offer to make the first assistant of that city's Mechanic Arts High School, Arthur D. Deane, the supervisor of the island's industrial training. Deane would ultimately decline this offer but accepted one as a temporary agent to the Puerto Rico Department of Education, observing and making a report back to the agency in January 1902 on steps needed to establish Puerto Rico's first industrial arts programs.

In 1901, former Holyoke mayor and congressman William Whiting invited the first civilian colonial governor Charles H. Allen to the city. Allen, an infamous figure in Puerto Rico's history as an American colony, was a former congressman from Lowell and Assistant Secretary of the Navy during the Spanish–American War who was appointed to head the island's new government by President McKinley, whom he had accompanied to Mount Tom two years earlier. During his visit Allen touted the construction of roads which had been completed with no-bid contracts as a resounding success, while also praising the tariff situation around the island's sugar industry as ideal. He would also emphasize the sugar growing capacity of the island and lament that less than half of the island's arable land was in production. During his short tenure as governor and the years that followed, he wasted no time in changing this to suit his own interests. By 1907 Allen would position himself as the robber baron of sugarcane, controlling an estimated 98% of the United States' sugar capacity through his American Sugar Refining Company, which vastly reshaped the economy of the island. By 1930, an estimated 45% of all arable land on Puerto Rico was dedicated to sugar plantations under Allen's control. At the time of his visit to the city a writer for The Republican would close the description of Allen's reception optimistically, comparing Holyoke with San Juan, remarking that the two cities were roughly the same population at that time.

While the first Puerto Rican immigrants would not arrive in Holyoke en masse until after the Second World War, its own history in Puerto Rican culture begins with Sixto Escobar's mainland debut at the Valley Arena. On May 7, 1934, Escobar defeated bantamweight contender and Canadian flyweight titleholder Bobby Leitham, in a fight that made headlines in local papers and was seen as a dramatic upset in the world of boxing. A few weeks later on May 22, Escobar faced his second opponent on the mainland, Joey Archibald, at the same venue, beating him handily before moving on to a rematch with Leitham in Montreal. These two matches marked an early chapter in a storied career; Escobar would go on to become Puerto Rico's first world champion.

In 1950, the Puerto Rico Industrial Development Company, other offices of the Puerto Rican government, in collaboration with the government of Argentina, assisted in a trial run of the first bagasse (sugar cane waste) based newsprint paper at the mills of the Chemical Paper Company. The demonstration production batch would be manufactured before more than 100 paper, sugar, and chemical magnates and representatives from more than a dozen other countries.

Early settlement + Historical Puerto Rican Population of Holyoke Year Residents Growth (%) Percent Total Pop. (%) 1970 ≈5,000 – ≈10% 1980 5,764 – 13.5% 1990 12,687 120.1% 29.0% 2000 14,341 13.0% 35.9% 2010 17,826 24.3% 44.7% 2020 19,597 9.9% 51.3% At the end of World War II, the government of Puerto Rico began the Puerto Rican Farm Labor Program, coordinating with the US Department of Labor to bring seasonal farm workers into the mainland, not unlike the Mexican Bracero program. Between 1947 and 1990 the program would bring in 421,238 Puerto Rican agricultural laborers to the United States. Many of these workers found work in Connecticut and the Pioneer Valley, particularly working for the Shade Tobacco Growers Agricultural Association.

Holyoke's history in Puerto Rican settlements first began around the mid 1950s, when a landlord named Domingo Perez, purportedly became the city's first Puerto Rican resident. By 1956 an article in The Republican reported on 1,000 Puerto Ricans in a self-described immigrant colony in the Greater Springfield area. The first to settle in the area were met with racial discrimination and open hostility, with one Boricua restaurateur describing their people being "treated like animals" at the time. This same family had followed a similar route many others would, having previously moved to the area from New York where they had previously settled in 1948. Another early report of the Puerto Rican community that same year appeared in a Springfield Union article of a wedding held at Holyoke City Hall on January 3, between a Carmen Hermandez and Jesus Mejias, both born in Porto Rico [sic] and residing on Main Street in South Holyoke, who would spend their honeymoon in New York City. At the time Hermandez reportedly worked for the Adams Plastics Co., a South Holyoke-based firm employing 175 workers which future-Mayor Samuel Resnic had cofounded. By this time the company, a maker of "pakkawood" composite handles, was sold to EKCO, however Resnic remained with the firm, and would travel to Puerto Rico himself as Mayor in 1963 while vacationing, representing one of Holyoke's earliest informal exchanges with the island.

By 1958, the Union had begun referring to a Puerto Rican community in The Flats neighborhood of Holyoke, also known as Ward 1. One of the biggest challenges with making inroads with existing communities was the language barrier of the first arrivals, with many only speaking Spanish. Some of the earliest programs working towards integration came from the Greater Springfield Council of Churches, which by 1961 had recruited a number of volunteers, many of whom were retired teachers, to help teach English to Puerto Rican women. Other early cultural exchange programs were held in churches such as Holyoke's St. Paul's Episcopal, which in 1956 hosted a lecture on Puerto Rican culture by a native of the island whose father had served as chancellor of the Episcopal diocese there.

In the 1960s, a large segment of the valley's Puerto Rican population was displaced when Springfield launched a massive urban renewal project in part to expand its highway system, razing many of the low-cost brick tenements between Metro Center and Memorial Square. During this time many would find low-cost housing in the blocks of Holyoke's lower wards, moving to former mill worker areas like South Holyoke and Springdale. Seeing the relative success of relatives and friends, in the 1970s a new wave of immigration began when a large number of families emigrated from New York City and Hartford, moving northward.

Mass migration and exclusion

"I thought I was the only Puerto Rican in town. Then sometime in 1971 I woke up one day and heard a lot of Spanish. By 1972 I became cognizant of what was a change in attitude. Some of the warmth was gone."—Josephine Carabello, director, Mount Holyoke Office of Compliance "Let's face it, we're here to stay...The first generation gets the brunt. Then it eases up. That's the way with every ethnic group, the Irish, the Polish and French-Canadians. Our tensions will ease."—Efrain Figueroa, sales representative for Nabisco "I don't see any reason why Puerto Ricans...cannot follow the same phases of other migrant groups. But we will always be considered a defined race. If you have a drop of black blood, you are non-white. Race is the most undetermined and difficult to define in terms of sociology. It means different things to different cultures."—José Efrain Martinez, teacher, Holyoke Public SchoolsQuotes from By the time many Puerto Rican families were being uprooted by Springfield's redevelopments, a large upsurge in new arrivals had occurred. In 1967 this new population was mainly low income and very young, with more than half of all Puerto Rican residents being school-aged children, while public agencies remained poorly equipped to provide for the community's needs. Reception to the community from those already in Holyoke and Springfield proved difficult not only due to social discrimination and racism but also as many businesses and government agencies lacked resources for Spanish speakers at a time when substantially fewer in the community spoke English. Far fewer translators were available at that time than today, and growing up in schools that did not speak their mother tongue, many in the younger demographic remained unable to read or write. This was exacerbated by a time when Holyoke saw a level of economic decline it had not witnessed before, or since, with 50% of all industrial jobs disappearing from 1955 to 1975; in this period, Puerto Ricans were witness to a changing colonial economy, leading many laborers to emigrate from the island. While more Puerto Ricans arrived in Holyoke in the 1970s, bringing the population to 5,764 or 13% of the total population by 1980, their numbers were fewer than the subsequent decade, and due to these economic circumstances the city as a whole would see a population decrease of nearly 11%, the most in its history.

The growth of Holyoke's own community, coupled with these aforementioned factors and substandard housing, led to an increasing gap between the Puerto Rican community and a police force that was described by a 1973 Police Foundation report as a group of "117 people, many of whom were related to each other" in the city of 50,000. The report goes on to say that representatives from the Model Cities Program and Governor Sargent's office urged greater outreach and would describe the relationship between the police and Puerto Rican community at that time as "the police [being seen] as brutal men with clubs, [while] the police saw the [Puerto Rican] community as tempestuous people with no respect for law and order".