Buccaneers of St. Croix and the USVI: Francis Drake

Stanford Joines

Excerpted from The Eighth Flag

 One of the most well-known Buccaneers to have walked the beaches of St. Thomas and St. Croix was Francis Drake. Drake was the first of 12 sons born to a Protestant preacher in 1540 in then Catholic England. Father Drake apprenticed his son to the master of a small channel trading ship. When the master died, he left the vessel to 15-year old Francis. After selling it, Francis sailed with his cousin John Hawkins in three expeditions to Mexico, which ended with the incident at Vera Cruz.

From 1528 to 1598, French and English Buccaneers, among them Drake and Hawkins (1570-71), were operating out of the Virgin Islands, including the islands of St. Thomas and Santa Cruz (St. Croix).

Drake made one of the most famous voyages of all time a few years later when he captained the Golden Hind in the world’s second circumnavigation. He captured the 120 ton Manilla Galleon, (better known to her crew as “Cacafuego,” literally, “fire shitter” or, if you will, “bad fart”) and got a nice haul of gold, jewels, and silver. 

Spain’s King Phillip II demanded that he be hung as a pirate when he returned to England. Instead, Queen Elizabeth, happy to have her share of the loot, knighted Drake. Hawkins successfully raided Spanish shipping as well and was also knighted. At this stage of their careers, they became Privateers, instead of Pirates. Later, both were brought into the English fleet as Admirals, helping defeat Spain’s great armada of 1588. England loved their pirates. England could deny responsibility for them when it was convenient, and knight them later.

In 1585, Drake sailed to the West Indies, notoriously hanging out in the passage that bears his name through the British Virgins. He left to sail up the coast of Florida, where he attacked Spanish towns. Heading up to Carolina to catch the Westerlies home, he stopped at Roanoke, the first English colony in America, and gave several Colonists’ lifts back to England, where they introduced tobacco, corn, potatoes, all of which rocked the European world.

In his most audacious attack, Drake boldly entered the heavily fortified port of Cadiz, Spain, destroying 30 new ships of war that were assembling to form part of an armada to invade England.

King Henry VII of England left the Catholic Church in 1534, creating a Protestant mostly, England. The Pope blessed a Spanish armada on its journey to punish the heretics and bring them back into the fold. One hundred thirty ships sailing in large crescent formation, the largest fleet of large ocean-going vessels ever assembled in history up to that time, appeared in the English Channel in July 1588. 

Famously, Drake finished his game of bowls after excited messengers ran to tell him of the arrival; he knew the unwieldy galleons would not be coming very fast. The fleet was to stop in the Spanish Netherlands to pick up an army and invade England. Drake and Admiral Howard deliberately set eight ships on fire and sent them downwind into the middle of the fleet off of Calais harbor. Some ships caught fire, but the biggest gain was that, though most made it out, they were never again able to organize effectively. The next day the English ships,  with their longer-range cannons, proved that the invasion was not going to happen.   

Unable to turn and sail against the wind for home, the Spanish fleet went over the top of Scotland, some over Ireland as well, and many wrecked in terrible storms on the rocky coasts. The blood of many young Spanish men who swam ashore mingled with that of single, Catholic young ladies, resulting in what is known as “Black Irish” and “Black Scots.”

In 1593, using the Virgin Islands as a base, Drake and Hawkins unsuccessfully attacked San Juan de Puerto Rico. A Spanish cannonball from El Morro castle passed through Drake’s cabin while he was on deck. Some records say that he led a landing party in an assault on La Fortaleza, was wounded in a duel with the Spanish commander, Pedro Suarez Coronel, and retreated to the ships. 

Drake and Hawkins returned to the Virgin Islands, but attacked Puerto Rico again. Many of the Englishmen came down with dysentery. Drake himself did, and the cousins (with Hawkins) decided to get away from the unhealthy island, sailing over to Panama after receiving information of a treasure fleet in Portobello. 

While sailing off to Portobello in January of 1596, Francis Drake died of dysentery caught in Puerto Rico. He was buried in the outer harbor in full armor, lying in a lead-lined coffin. Sir John Hawkins died of malaria shortly after and was buried at sea in the Caribbean, as well. 

Sir George Clifford sailed to San Juan three years later on his 38-gun Scourge of Malice (renamed the Red Dragon) and found Puerto Rico unable to defend itself due to that same continuing epidemic of dysentery. San Juan fell on June 30, 1598, but the English left a couple of months later, not wanting to follow Drake to the bottom of the sea.