Beginning his reign amidst native dissatisfaction with the encomiendas system and the acquisition of land territory that his predecessor allowed, the new leader soon formed a coalition that included several southern caciques, such as Urayoán, Coxiguex, Yauco, Jumacao, Loquillo, Orocobix, Guayama, and "Luis" among several others, and declared war on the European settlers.
Throughout 1512, Spanish commanders Juan Cerón and Miguel Díaz led a series of horseback incursions into the territory of the ruling Caciques, destroying their villages (known as yucayeques) and taking as many slaves as possible in the process.
[8] During that year, the local Spanish carried out 23 incursions against the natives, and viceroy Diego Colón ordered additional retaliatory attacks after the Taínos burned down the settlement of Caparra.
[21] Aware of the events that had happened in the adjacent island of Hispaniola (previously named Kiseya by the native Tainos in the region) in the fifteen years since the Spanish first landed there, the caciques (a title akin to "chiefs") of Borikén tried different approaches.
[23] Ponce de León found himself before the High Chief, his mother (and counselor) and her husband (actual relation to the cacique is unclear, but it could have been his father or stepfather), an uncle, two sisters, and a brother.
[31] Alluding to a royal decree and at the demand of Juan Cerón, representative of viceroy Diego Colón, the newly crowned Agüeybana II was to be requested to assign 40 naboría Taínos to serve Sotomayor's Villa de Tavora.
[36] Sotomayor was succeeded by Juan Gil Calderón, right-hand man of Ponce de León, who was involved in the slave trade of Taínos and had received 150 natives from one of the lesser caciques under Aymaco, one of Agüeybana's subjects.
[41] In July, Royal Secretary informed Juan Cerón and Miguel Diaz, who would replace Ponce de León political and military leaders of Puerto Rico, of the ongoing situation and issued a series of specific orders to try and qualm it.
[45] During the months that followed, Ponce de León requested that a brigantine be built and brought from Hispaniola to counteract Carib canoes that were entering into Borikén/San Juan, marking the first mention of foreign natives becoming involved in the conflict.
The Taíno offensive frustrated the monarchy, who ordered Cerón and Díaz to rebuild a destroyed settlement at Añasco, from which they would carry out the mining of gold and resources from the Otoao.
[7] The arrival of 1513 registered an increase in the Spanish population, fueling the expansion of the nascent colonial government and its mining operations due to the discovery of new deposits in the terrains of Loquillo.
[7] Diego Guilarte de Salazar was then able to set camp at Guánica and the Spanish rebuilt San Germán and began processing mined gold, supplied with a large contingent of natives captured both locally and at the Lesser Antilles.
[58] However, the Taínos mounted a counter-offensive led by the High Chief, taking refuge at Daguao (the southeastern and coasts, comprising the municipalities that run from modern-day Humacao to Luquillo such as Fajardo, Ceiba, Río Grande, and Naguabo) which due to its inhospitable terrain complicated the incursions of the conquistadores.
[58] Agüeybana II's faction, fortified with the arrival of caciques and natives from St. Croix and other Antilles, targeted the dispersed Spaniards that had ventured into the region in search of gold and work hands.
[63] Eight belligerent caciques led a force of around 350 men from their alliance and burned down the settlement, killing 18 Spaniards and took with them around 4,500 pesos worth of gold, while the remaining settlers fled into Ponce de León's residence.
In this offensive, the caciques Guayervas, Mabo, Yabey, Cayey, Guariana, Guayaboa, Guayama, Hayaurex, Baguanamey, and Yauco, were detained on suspicion of participating in the attack and sent to Hispaniola.
[71] In March 1515, Gil noted in correspondence to Hispaniola that a slaving armada under his command had cornered Agüeybana II in the adjacent islands, likely as part of the local Taíno community that had moved to Guadeloupe.
[84] The author also recycles the figure of Juan de León, claiming that he was the one responsible with killing the mysterious cacique, which he identifies as Agüeybana II himself citing the reaction of the Taínos to his death.
[85] Castellanos concludes his account here, depicting Ponce de León as issuing an order not to pursue the retreating natives and claiming that this was the end of the war, omitting subsequent battles.
[89] Like his predecessor, Abbad y Lasierra depended heavily on the accounts of Oviedo, Castellanos and Herrera, repeating the claim that Juan de León had killed Agüeybana during a final battle.
[90] In 1827, American historian Thomas Southey wrote about the topic in Chronological History of the West Indies, being the first to note that Gil had cornered Agüeybana II at Guadeloupe.
[92] Brau in particular, disregarded both the impact of the conflict and the reputed bravery of the Taíno, noting his belief that they were "unworthy of historic immortality" and argued that the subsequent orders to counterattack the caciques were due to a communication delay because Agüeybana II was already dead.
[95] A parallel school led by Spanish-born historians opted instead to diminish the role of the Taínos in Puerto Rico while exalting Ponce de León, making sparse mentions of Agüeybana, mischaracterizing them as docile and instead giving more prominence to the Caribs in their narrative, also claiming that the belligerent army was mostly composed by them.
[96] Following the Spanish–American War, Brau's narrative of the events gained traction in the new colonial government due to his promotion as "Official Historian of Porto Rico" by appointed governor Hunt.
[60] He, along Ricardo Alegría and Álvaro Huerga, assumed that the attack was carried out by Carib forces, but eyewitness accounts, a Taíno confession and the testimony of those involved in the defense of Caparra, such as Francisco Juancho, blame the belligerent caciques.
[103] In 1514, Ponce de León delineated the political division that he would recognize, which separated the main island of Puerto Rico in two and ignored the authority of the caciques, assigning the Cayabo to the jurisdiction of San Germán.
[54] In 1992, Irvin Rouse revisited the issue and reclassified the pre-colonial inhabitants of St. Croix as oriental Taínos, noting that they were culturally part of the Puerto Rican circle.
[110] This, combined with a previous plague that the natives were unprepared to overcome, diminished their role in the colonization's heavy work, which was now progressing to plantations and moving away from mining, in favor of more African slaves.
[111] However, this interest also led to the mythification of the figure being accepted as fact, with fictional accounts of his relationship with his sister or his motivations for attacking the Spanish becoming widely spread through the work of authors Alejandro Tapia and Cayetano Coll y Toste.
[113][114] The Numismatics Society of Puerto Rico minted a medal commemorating the event, illustrating a cacique and several natives in combat which was based on the narrative of Ricardo Alegría.