The experts had to be both white and Catholic, requirements that appealed to Irish planters, overseers and skilled craftsmen residing in the nearby British and Danish colonies. No one knows for certain how many of them took advantage of the opportunity, but their noticeable presence in Puerto Rico in the last third of the eighteenth century appears to suggest that a considerable number surely did. Felipe Doran, a native of Carlow, was one of them (AGI-Ultramar, leg. 405, Cámara de Indias to King, 16 January 1804).

Alejandro O’Reilly, of County Meath, who migrated to Spain in his early teens and later joined the Hibernia Infantry Regiment, was the highest ranked Irishman serving in the Spanish armed forces to come to Puerto Rico around this time. A career officer holding the rank of Field Marshall in 1765, he was dispatched to Puerto Rico a few years earlier in response to the British occupation of Havana. His memoria, or report, of Puerto Rico enabled the Spanish Crown to get a better sense of the island’s military weaknesses and economic potential. Credited with re-organising the local militias, O’Reilly also set out to revamp the fortifications around San Juan (Torres 1969; Beerman 1982).

The latter task fell to Colonel Tomás O’Daly, a native of County Galway who began his military career as a second lieutenant under Juan (John) Sherlock’s Ultonia Regiment in 1744. Trained as a military engineer in the Academia de Barcelona, he served in Madrid, El Ferrol, and Girón (AGS-Guerra, legs. 2668 and 3091). Granted land in the vicinity of San Juan, O’Daly began developing it into a thriving sugar hacienda (AGI-SD, leg. 2300, 15 July 1761). With that step, he joined an embryonic Irish immigrant community that would come to be associated with the growth of commercial agriculture. Upon his untimely death in 1781, his brother Jaime took over the property and helped raise Tomás’s three children, Isabel, Manuel, and Demetrio (AGI-SD, leg. 2393, 6 July 1797).

A colourful character, Jaime left Ireland possibly in his late twenties and took up residence in Cádiz, Spain, around 1763. Two years later, he sailed off to the Dutch Caribbean colony of Saint Eustatius. When a Spanish fleet ran aground near the British colony of Anguilla, Jaime and a business partner came to its aid. In compensation, the Spanish Crown gave him a temporary licence to export products from Puerto Rico to recoup the funds both had spent on refitting the stranded convoy. He applied for a licence to embark from Cádiz to Puerto Rico on 6 November 1775, but did not leave until 23 February 1776 (AGI, Casa de Contratación, leg. 5522, no. 1, r. 21).

Sheltered by Tomás, he remained on the island beyond the stipulated time. Over the next decade, Jaime built up a reputation as a successful sugar and tobacco planter and merchant, with connections across the non-Hispanic Caribbean and Europe (Torres 1962; Pérez Toledo 1983). In 1793, detractors cited his foreign status to block his nomination to a post on the prestigious San Juan city council (AGI-SD, leg. 2372, 16 December 1793). When the Spanish Crown appointed him director of the Royal Tobacco Factory in 1787, one of his fiadores (guarantors) was Bernardo Ward, the Irish economist and adviser to the Spanish monarch King Ferdinand VI (Chinea 2001).           

Jaime claimed blood ties to Lieutenant Timoteo O’Daly and Captain Pedro O’Daly, officers of the Hibernia Regiment that took part in the 1781 Spanish capture of Pensacola, Florida. Lieutenant Colonel Arturo O’Neill, also of Hibernia, co-led the final assault that dislodged the British forces. For his feat, Spain named him Governor of West Florida and subsequently appointed him to the Supreme Council of War (Murphy 1960: 220-22; Beerman 1981: 29-41; Walsh 1957: 38). In 1792, he had been placed on the short list of candidates to replace Governor Miguel de Uztáriz, who passed away while en route to Spain (AGS-Guerra, leg. 7146). His two nephews, Julio (or Tulio) and Arturo O’Neill y O’Kelly, born in Saint Croix, moved to Puerto Rico in 1783 with their slaves and plantation equipment (AGI-SD, leg. 2364, 15 October 1783). Another Irish planter residing in Saint Croix, Tomás Armstrong followed them in 1791 (AGI-SD, leg. 2393, 16 February 1791).

Others were not so lucky, no doubt because their intentions would have violated regulations that banned foreigners on Spanish soil from partaking in the navigational and commercial trades. Such was the case of Juan Tuite, a resident of Saint Croix with business ties to England. In 1766, he proposed setting up an Irish colony of one hundred well-to-do families in Puerto Rico. He asked for authorisation to bring in provisions, tools and slaves not just for his settlers, but also to supply Puerto Rico and other Spanish American colonies. Clearly, Tuite’s mercantile ambitions contravened the Laws of the Indies, which could explain why his project was not favourably received (AGS-Estado, leg. 6961, exp. 14, 1766).  

In order to gain approval to import slaves into Puerto Rico, Tuite needed a licence. This may have been possible, especially during acute labour shortages. But the Spanish Crown had already granted an exclusive slave importation right, or asiento, to a private party or company between 1765 and 1789. Thereafter, the Crown opened the trade in African captives to all its subjects and foreigners upon payment of the applicable slave importation and sales duties. Joaquín Power y Morgan came to Puerto Rico in connection with the Compañía de Asiento de Negros and married a local Creole, María Josefa Giralt (AGI-SD, leg. 2389; AGMS, 1ra. Sección, leg. P-2619). His paternal grandfather Pedro Power was a native of Waterford who emigrated from Ireland to Bordeaux. Father José Bautista Power, born in the French port city, relocated to Biscay, northern Spain (Bilbao Acedos 2004: 102-3). Born in 1775 in San Juan, one of Joaquín’s sons, Ramón Power y Giralt, became Puerto Rico’s representative to the Spanish Cortes in 1808 and later president of the same legislative assembly (Caro 1969).

Several servicemen of the Irish regiments that saw action in Central and South America around this time also remained behind in the Hispanic Caribbean. Patricio O’Haurahan and Cristóbal Conway, both of the Irlanda Regiment, were two of them (AGMS, leg. 7147, exp. 33, 24 July 1790 and exp. 40, 25 May 1790). A handful of lesser known Irish settlers also came to Puerto Rico around this period. Besides the O’Dalys and O’Neills, at least two other separate pairs of brothers, David and Jaime Quinlan and Miguel and Patricio Kirwan, established sugar haciendas. Like the O’Dalys, the Kirwans also came from County Galway (AGPR, Loíza, carpeta 1, 1791-1803). Their fellow countrymen, Miguel Conway, Patricio Fitzpatrick, Felipe Doran, Jaime Kiernan, and Antonio Skerret, were also commercial farmers around northern Puerto Rico, from Toa Baja in the northeast to Luquillo in the east (Bermejo-García 1970: 125-26). Since some of the latter began as overseers, there is a strong possibility that they originated from the nearby non-Hispanic colonies where former Irish servants with limited prospects for social mobility had little choice but to seek greener pastures elsewhere (Walters 1982).

The 1797 English Invasion of Puerto Rico

In the early morning of 17 April 1797, a large convoy approached the waters off San Juan, the capital of Puerto Rico. Even though it hoisted no flags at first, a state of war between Spain and England dictated caution. So started the report filed by Brigadier Ramón de Castro, Captain General of Puerto Rico, about the largest and last British attempt to wrest territories in the Americas from Spanish control. Between sixty and sixty-four vessels ferrying an estimated ten thousand combatants, including German and black auxiliaries, took part in the attack. The outbreak of hostilities began the following day and ended disastrously for the aggressors on 1 May (Tapia y Rivera 1970: 669-718).

For British warmongers, the attack was a costly miscalculation. They had grossly under-estimated both the citadel’s ability to fend off enemy strikes and the tenacity of its defenders. During the two-week conflict they were held back by an impregnable fortified system circling the city, working in tandem with organised resistance forces deploying both frontal charges and guerrilla tactics. Prevented from gaining any significant ground, the invaders abandoned a large quantity of their armaments and re-boarded their ships in the cover of night. It was a resounding victory for the island’s armed forces, the overwhelming majority of whom were local people (Tapia y Rivera 1970: 669-718).