
Pirates, Poets and Pilots
The history of the Bulwark of the Indies seen through the genes of Col. Angel Castillo y Quesada. Part 2 of 3.
To my grand-uncle Gabriel Rodríguez, who through his writing saved the Castillos from the oblivion of exile. I never met him but his work animates mine.
Colonial Puerto Príncipe’s labyrinthine streets gave it a medieval air that it still sports, very different from the Renaissance-minded checkerboard layouts of most new cities founded by the Spaniards in the New World. Legend has it that it was built this way to throw off the sense of direction of invading pirates. True or not, our forebears had to deal with a lot of these greedy hearties.
Sometimes they fended them off successfully. That was the case for Lorenzo Borrero Trujillo. A Canary Islander, he sailed to Cuba in 1625 with Pedro de Fonseca y Betancourt, the new governor of Santiago. As mayor of the coastal city of Bayamo, he defeated an invasion of several hundred Dutch pirates who had looted the area surrounding Puerto Príncipe.
Sometimes invaders overwhelmed the town. Henry Morgan did so in 1668 before his famous exploits in Panama, murdering locals and extracting a large ransom. At other times, the price of victory was dear. Spaniards managed to hold off the French pirate Grammont in 1679, but several local notables, including our ancestor Francisco de Varona y Saravia, lost their lives in the battle.

The threat of piracy, a result of volatile European politics mixed with the general lawlessness of the Caribbean, hung heavily over the initial settlers and their descendants for nearly two centuries. It’s the subject matter of the first work of literature written in Cuba, “Espejo de Paciencia,” the oeuvre of our ancestor Silvestre de Balboa, who was the official clerk of the Puerto Príncipe ayuntamiento, or city council, just a few of generations after the Conquest. (Balboa’s daughter Leonor married a great-great-grandson of Vasco Porcallo.)
Written in 1608, Espejo de Paciencia is an epic poem about how the people of Bayamo freed the bishop of Cuba from French corsair Gilberto Giron. They were led by their mayor, Gregorio Ramos. It is thought that Balboa, a native Canary Islander with roots in the region around Leon in northwestern Spain, lived in Bayamo before moving inland to Puerto Principe and was well acquainted with the protagonists of his tale.
The poem is preceded by several sonnets written by local principeños with a taste and some talent for poetry. One of them was Pedro de la Torre Sifontes, also our abuelo.
Habeis echado el sello á vuestra ciencia
con tan sublime obra, buen Silvano,
diciendo del Ilustre Altamirano
el valor, cristiandad, y la paciencia.
Infalible verdad fué la pendencia
que Ramos tuvo con el luterano;
vengó al Pastor la poderosa mano,
dándonos á entender su omnipotencia.
Que al humilde levanta y le da loa,
y al soberbio arrogante echa por tierra;
estilo del Señor muy ordinario.
Recibe de mi mano, buen Balboa,
este soneto criollo de la tierra
en señal de que soy tu tributario
As for Balboa’s work, he crafted one of the first literary descriptions of the island of Cuba. First he sings about the mercantile nature of the colony, which lived off of selling cowhides and dried beef to ships of all nations. Most of this trade was in the black market, because Spain was supposed to have a commercial monopoly.
Tiene el tercer Filipo, Rey de España,
La ínsula de Cuba ó Fernandina
En estas islas que el oceano baña,
Rica de perlas y de plata fina.
Aquí del Anglia, Flandes y Bretaña
A tomar bienen puesto en su marina
Muchos navíos a tocar por cueros
Sedas y paños y á llevar dineros.
Then Balboa brings up the martial spirit of the first Cubans, who fought off the pirates uttering the legendary battle cry of the Reconquista: “¡Santiago, cierra España!”
En esto, cual leones tras de gamos,
Salen los nuestros ya de la montaña;
Y en delantera el buen Gregorio Ramos,
Diciendo “¡Santiago, cierra España!”
Y van cubiertos de los verdes ramos
Con que la Dafne triste se acompaña
Después que de certeza fue cubierta,
Cual si tuviesen la victoria cierta.
Part of what drew pirates to Cuba was the Spanish Treasure Fleet. Dozens of galleons sailed from Spain to the Spanish Main and Mexico, gathering all the riches of the mainland, and waited out hurricane season in Havana. The wealth these ships carried was so fabulous that Dutch schoolchildren still sing about the exploits of wily privateer Piet Hein, who captured the fleet in 1628.
The fleet also brought to America merchandise from Spain, and more colonists. At the helm of one of its galleons was the founder of the Castillo family in Cuba.
Juan Lopez del Castillo was a young Andalusian. We know little about his origins; Santa Cruz y Mallen says his father Bartolome Lopez was born in Catalonia, and his mother Isabel del Castillo was from Seville. We know Juan was baptized in 1613 in the port of Santa Maria, in Cadiz.
At some point, perhaps as a child or a young teenager, Juan must have gotten on a ship, then enrolled in the school for ship pilots at the Trading House of Seville, the institution that ran Spain’s colonization effort. The academy had been created a century and a half earlier by Amerigo Vespucci, the Italian explorer our continent is named after, to make sure the officers in charge of the king’s ships knew how to navigate the tricky waters of the Carrera de Indias (the Highway of the Indies), as the route was known.
Luckily, we have a copy of Juan’s final exam in 1645, in which he proved that he could sail ships to the ports of New Spain, Puerto Rico, Santo Domingo, Honduras, Campeche, La Habana, Jamaica and other islands. Five years later he took another exam, attesting his ability to sail to Tierra Firme (modern day Venezuela and Colombia). Here’s a page from the document:

It’s unclear to us whether Juan, who Santa Cruz y Mallen says eventually became captain, made a definite jump across the Pond. Two of his children did, however. In 1692, after the end of the Golden Age of Piracy, Juan’s son Bartolome, our ancestor, a native of Cadiz, got a permit to settle in Santiago de Cuba, where his brother had established himself as a merchant. Thanks to the persnickety officials of the Trading House (and the intern charged with scanning old documents at modern-day Spanish Ministry of Culture) we have the pixels to prove it.

Bartolome moved to Cuba with his wife, Maria Pimienta, but she died soon after; he soon married a santiaguera, Andrea Bañares Guzmán y Machado, and became the founder of what would become a large and relatively prominent family.
His son Francisco would be mayor of Santiago, which was Cuba’s second largest city; his grandson Fructuoso would move inland to Puerto Príncipe, where he would also become mayor and a big cattle rancher. He married Maria de las Mercedes Betancourt e Hidalgo, a descendant of the first Conquistadors of the area.
The fourth generation in Cuba — Fructuoso and Maria’s kids — would be the first ones to to fan the flames of freedom. It was the time when the sordid Ferdinand VII had abdicated to Napoleon and the peninsula was in turmoil, tempting Spanish American colonists to break away from what had become a burdensome empire. In 1809, Diego Antonio del Castillo y Betancourt wrote up a flyer denouncing the evil Spaniards and advocating for a free Cuba.
The beleaguered royalist authorities in Havana first sought to imprison him, then relented, after the notables of Puerto Príncipe threatened to raise an army against the capital. In the end Diego Antonio made his peace with the government, becoming mayor and dedicating the rest of his life to building Príncipes first cemetery (he was the first man buried there.) We descend from his brother Martín, whose children and grandchildren would rekindle Diego Antonio’s struggle.
Read also:
Hombres de todo mar y toda tierra: the convoluted story of a Spanish American family
A Spanish Life: the 19th century adventures of Natalio Gonzalez y Fernandez, Part 1 of 2
The Lions of Wadras: the 19th century adventures of Natalio Gonzalez y Fernandez, Part 2 of 2