1565, St. Augustine, Florida | the two Menéndez

Preface: an brief recap of history of immigration of US.

As mentioned previously, even though Spain first discovered New Land, Portugal was the one established the navigation system and stabilized the routes to Africa. Portugal — small hinterland, blocked out of the spice trade, no internal growth option, forced to make exploration a state strategy starting with Ceuta in 1415, decades before Columbus ever sailed. Spain, by contrast, gets framed almost as a free-rider on a navigational toolkit Portugal had already de-risked. Spain's motive wasn't structural desperation — it was post-Reconquista momentum and a single high-variance bet that happened to pay off spectacularly. Portugal had a head start of decades and was the one steadily building toward Asia — but it was working a different route (down the African coast, around the bottom, then east), and Columbus's specific pitch — sail west across open ocean to reach Asia — was something Portugal had already evaluated and turned down. Columbus himself was Genoese, but since he sailed under the Spanish crown, and that's why Spain (not Portugal) ended up with the claim and the resulting rivalry with Portugal that produced the Treaty of Tordesillas in 1494.

As everyone knows, Columbus was trying to find a westward sea route to Asia. The 1492 landfall accelerated rivalry between Spain and Portugal over new lands, and Pope Sixtus IV had previously granted Portugal rights to land south of the Cape Verde islands, which is part of why the Portuguese king initially argued Columbus's discoveries should belong to Portugal, not Spain. Spain got a friendlier pope to rule otherwise, and the dispute was settled by drawing a line down the Atlantic. Columbus initially pitched his westward voyage to King João II of Portugal. Portugal rejected him because his estimated travel distance was too short — he badly underestimated the size of the globe — and because Portuguese explorers had already rounded the Cape of Good Hope, giving them a known eastern route to Asia that didn't require betting on an unverified shortcut. Portugal had real intel (decades of coastal surveying) telling them Columbus's math was wrong, so from their position it looked like a bad bet, not a visionary one. Spain had just finished the Reconquista in January 1492 — military, financial, and religious momentum was all pointed outward looking for a new project, and Ferdinand and Isabella were also motivated by status competition with Portugal specifically. So Columbus's pitch landed with a country that had mobilized energy and a rival to outdo, not a country with the best navigational judgment. Columbus was working from a wrong premise that happened to work out. He believed the earth was much smaller than it actually is, didn't know the Americas existed, and fully expected to land in Asia — he hit land in the Caribbean on October 12, 1492, and (per Britannica Kids) died still believing he'd reached Asia, not a separate continent.

March 20, 1565

King Philip II appointed Pedro Menéndez de Avilés as adelantado of Florida via a contract (asiento) signed March 20, 1565, with the explicit goal of finding a suitable location for a permanent settlement that could defend the Spanish treasure fleet and protect Spain's claimed territory from other European powers. The deeper trigger: Philip II was alarmed by a French Huguenot (Protestant) settlement on a strategic stretch of Florida coast, and sent Menéndez specifically to deal with it. This wasn't colonization-for-its-own-sake — it was a Catholic empire eliminating a Protestant rival outpost, with permanent settlement as the byproduct.

Menéndez set sail from Cádiz on July 28, 1565, with a fleet led by the 600-ton flagship San Pelayo, carrying over 1,000 sailors, soldiers, and settlers. Other sources put the total expedition closer to 2,000 people aboard 11 ships, of whom only about 800 actually reached Florida's shore — meaning well over half the original expedition was lost or turned back before they even arrived. The land was sighted on August 28, 1565, the feast day of St. Augustine, after which the settlement was eventually named. Menéndez wasn't just sailing to an empty coastline. He was in a race to reach Florida before French captain Jean Ribault, who was heading to reinforce Fort Caroline. The two fleets actually crossed paths — on September 4 they met at the mouth of the St. Johns River and exchanged fire in a brief, inconclusive skirmish. Menéndez landed again on September 8, formally declared the land for Philip II, and officially founded the settlement, naming it San Agustín. The Spanish occupied structures in the Timucua town of Seloy, whose chief was allied with Laudonnière's French. A chaplain, Father Francisco López de Mendoza Grajales, celebrated what's sometimes called the first Thanksgiving Mass on the grounds — predating Plymouth's Thanksgiving by 56 years, a detail that tends to surprise people raised on the Pilgrim version of that holiday.

Eleven days after founding St. Augustine, Menéndez marched his soldiers overland to Fort Caroline and launched a surprise attack on September 20, killing all the adult men they found while sparing women and children — 132 Frenchmen died. This wasn't incidental violence; it was the actual point of the expedition. Worse followed: Ribault's fleet was wrecked by a storm near Cape Canaveral, and when Menéndez found the surviving 150–350 Frenchmen, they surrendered after negotiations — and the Spanish executed nearly all of them in the dunes near an inlet that became known as Matanzas, Spanish for "slaughters." St. Augustine's foundation is inseparable from a religious massacre — Catholic Spain annihilating a Protestant French colony, justified explicitly as killing them "Not as Frenchmen, but as heretics." English pirates and soldiers attacked and burned the town repeatedly during the 1600s, including Sir Francis Drake's raid on June 6, 1586, which burned the settlement and drove survivors into the wilderness (Drake then moved on to Roanoke rather than capitalizing on the win). Spain eventually responded by building the Castillo de San Marcos starting in 1672, completed just in time to survive a major British attack in 1702.

St. Augustine became home to the oldest continuously occupied settlement of European and African American origin in the United States. Specifically: a free Black settlement called Fort Mosé formed north of St. Augustine, founded by Francisco Menéndez — a man born in Gambia, enslaved in English South Carolina, who fled to Spanish Florida, fought in the Yamasee War, and in 1738 received Spanish permission to establish the village after converting to Catholicism and pledging loyalty to the crown. This is, depending how you frame it, one of the earliest organized free Black communities in what's now the US — built specifically because Spanish Florida offered freedom that English Carolina didn't.

Fort Mosé, 1738

In 1693, King Charles II of Spain issued an edict stating that any male slave escaping from an English plantation to Spanish Florida would be granted freedom, provided he joined the militia and converted to Catholicism — one of the New World's earliest emancipation proclamations. Important to be clear-eyed about why: welcoming refugees struck an economic blow against the English colonies while adding skilled workers and Catholic converts to Spain's own colonies, and crucially, these freed Africans could be formed into a militia to defend St. Augustine from the British. This is the same caveat that applies to Goncharova's icon paintings or Larionov's backdated canvases in your other research — the generous-looking policy and the cynical strategic calculation are the same act, not two competing explanations.

Born around 1704 in West Africa, likely along the Gambia River, of Mandinka descent, Francisco Menéndez was captured by slave traders sometime between 1709 and 1711 and shipped to British Carolina. He escaped to Florida and was sold as a slave to Francisco Menéndez Márquez — which is where he got his name, baptized Catholic, but still enslaved. In 1726 he was appointed captain of St. Augustine's Black militia while still legally enslaved, and solidified his leadership status by helping defend the city from a British attack in 1728. So: a man led Spain's Black militia in combat for over a decade before Spain freed him.

Menéndez directly petitioned the Spanish crown, arguing it was unacceptable that only some fugitive slaves had been freed while others hadn't, even though Spanish conditions were comparatively favorable to British chattel slavery — the runaways had upheld their end of the bargain by converting. He successfully petitioned for his own freedom and that of 31 others. By 1738 there were about 100 Black people, mostly Carolina runaways, living in what became Fort Mose, and on March 20, 1738, Governor Manuel de Montiano finally officially freed all runaway slaves and established the fort to house them. Montiano installed Menéndez as captain of the free Black militia and de facto leader — an obvious choice given he spoke four languages and had a decorated military record.

The settlement had a wall around it with dwellings inside, plus a church and an earthen fort, and the freedmen used their own skills in carpentry, masonry, and blacksmithing to build it. Most Africans in Spanish Florida — free and enslaved — made up about ten percent of St. Augustine's population, coming not just from West Africa but from Cuba, Jamaica, Barbados, Antigua, Venezuela, Colombia, and the Canary Islands, and cross-cultural marriages were common and legal, fostering a genuinely multi-ethnic society blending African, Spanish, and Native American traditions. Word of Mose reached South Carolina and Georgia and attracted escaping slaves, and the fort's existence is believed to have helped inspire the Stono Rebellion of September 1739 — one of the largest slave uprisings in colonial American history. That's a direct causal line worth sitting with: a free Black Spanish fort in Florida likely helped trigger a slave rebellion in British South Carolina. War broke out between England and Spain in 1740, and the English sent thousands of soldiers and dozens of ships to destroy St. Augustine, blockading and bombarding the town for 27 consecutive days. Fort Mose was one of the first places attacked; Menéndez's militia briefly lost it but recaptured it, repelling the English. The fort was destroyed in the fighting, but the counterattack — Spanish troops, Indigenous allies, and the free Black militia together — defeated Oglethorpe's forces.

After the fort's destruction Menéndez became a privateer to earn income, and in 1741 was captured by a British privateer ship. Recognized as Fort Mose's captain, he was tied to a cannon, given 200 lashes, threatened with castration, and had his wounds pickled in salt as further torture, then sold into slavery in the Bahamas. Somehow — the record doesn't say how — he was back in Florida by 1759, once again leading the rebuilt Fort Mose. Spain ceded Florida to Britain in 1763 at the close of the Seven Years' War. In August 1763, Menéndez, his wife María de Escovar, and the roughly 50 remaining residents sailed to Cuba on a schooner called Our Lady of the Sorrows, landing at Ceiba Mocha and founding a new settlement they named San Agustín de la Nueva Florida. Once Spanish St. Augustine no longer existed, Fort Mose had no purpose — its entire reason for being was tied to defending a city that was no longer Spain's. It was designated a US National Historic Landmark on October 12, 1994, and the actual site was lost for over two centuries until Florida Museum archaeologist Kathleen Deagan located it in the 1980s, working with then-doctoral-candidate Jane Landers, who together identified the approximate sites of both the first and second forts. 🌻