Embarked on his flagship “The Pelican”, whose construction was sponsored by the English Crown, Francis Drake made the second circumnavigation of the globe in 1579 when he took the opportunity to assault the helpless Spanish coastal towns in the Pacific, who had not yet known greater European threat than the one presented by the Portuguese and Spanish. On his return to England, the pirate was received as a national hero and knighted by the Queen. Willing to overlap what the Spaniards had achieved 55 years earlier with the Magellan-Elcano expedition, the English celebrated Drake’s arrival as a landmark of world navigation. For years, luck continued to accompany Drake, who kidnapped Portuguese and Spanish pilots to grow his legend, but luck itself abandoned him at the worst time. The Spanish Caribbean returned part of the affronts committed in 1596, the year of his death and his most humiliating defeat.

Portrait of Sir Francis Drake painted by Marcus Gheeraerts the Younger

Francis Drake gained his reputation as a soldier by looting Spanish ports in the Caribbean when England and the Spanish Empire were not even officially at war. Under the command of his second cousin John Hawkins, he learned at the age of 13 years old how profitable it was to attack Spanish ports by taking advantage of poor Hispanic defenses and the lucrative slave trade business, but this did not prevent him from suffering in person a major defeat during those years. In 1567, Hawkins made his third onslaught against Hispanic possessions. After taking 450 slaves in Guinea and Senegal, he set sail for the Caribbean commanding six ships, including “The Judith”, captained by Drake. A storm forced them to head to Veracruz where, pretending to be part of the Spanish Navy, forced Viceroy Martín Enríquez de Almansa to deliver supplies to them. To his misfortune, within a few days, the authentic Spanish navy arrived in Veracruz. Four pirate ships were sunk, 500 crew members shot down and profits from smuggling slaves were acquired almost entirely. Drake and his cousin were luckily able to escape. They were determined to avenge that humiliation in the following years.

The opportunity of the “poorly-defended ports”

Drake’s first individual performance (good enough to be mentioned) occurred in 1572. A year after the best generation of Spanish sailors won the battle of Lepanto, Drake ravaged defenseless ports in the Caribbean, including Nombre de Dios, on the isthmus of Panama, and Cartagena de Indias, and captured a Spanish convoy loaded with gold and silver with the help of French pirate Guillaume Le Testu. This action brought great fortune to Drake and made the English Crown appoint him the objective of attacking every Spanish affair in the Pacific.

Drake’s circumnavigation of the world was hugely lucrative. The loot obtained was valued at 250,000 pounds, a sum comparable to the annual budget of the British Parliament. On April 4th, 1581, Queen Elizabeth I jumped on Drake’s flagship in person and knighted him in situ. All of a sudden, the pirate had become a respectable man, with his seat in Parliament and with responsibilities within the Royal Navy. In this context, with the war already officially declared between the two countries, the Queen appointed the English privateer as the commander of a fleet of 21 ships and 2,000 men with the objective of attacking the Spanish Caribbean again in 1586. As Carlos Canales explains in the book “The Rules of wind: face and cross of the Spanish Navy in the Sixteenth Century”, despite the initial success in Santo Domingo and Cartagena de Indias, the final loot of 200,000 ducats was insufficient to cover the damage recorded in eighteen of the ships and the death of half of the crew.

Tired of”‘seeing his beards scorched”, a quote coined by Drake himself, Philip II of Spain made the decision to attack the English on his own territory in 1587. Preparations for this task were taken by Alvaro de Bazán, one of the heroes of the battle of Lepanto, but on April 29th of that year Drake attacked the port of Cadiz and sank twenty Spanish ships. During the same expedition, the English captured near the island of San Miguel, in the Azores, a carrack from India with a treasure worth 140,000 pounds.

Within the strategy to defend himself against the Spanish attack of 1588, Drake was appointed Vice-admiral of the English fleet under Admiral Charles Howard. An English legend tells that Francis Drake was bowling in the town of Plymouth when he was warned of the arrival of the fleet that Philip II of Spain had sent against Queen Elizabeth I. “We have time to finish the game. Then we will beat the Spaniards,” the privateer said before throwing the next ball. An implausible episode that Naval Historian Agustín Rodríguez González resembles with the classic “foundational myth” – in his book “Drake y la Invencible” – to hide an embarrassing truth: Europe’s worst-kept secret caught the main body of the English fleet still anchored and with their guns far from ready. Drake, with no real naval warfare experience, was repairing and supplying his ships after a failed attempt to ambush the Spanish fleet during their departure. Plymouth’s fleet was cornered.

“We have time to finish the game. Then we will beat the Spaniards,” the privateer said

The Duke of Medina-Sidonia, the Spanish commander of the fleet, decided to remain far from the seaside, going against the opinion of the old guard officers who had served with his predecessor, Alvaro de Bazán, who had died during the arrangements for the fleet in Lisbon. This decision condemned the Spanish Navy to wander into a disaster without clear objectives apart from picking up the troops waiting in Flanders, something that Alexander Farnese – commander of that infantry – did not put much effort into. Without a clear engagement in naval combat beyond the tireless British harassment, Drake had his most important moment during the fight, again in Plymouth, where Diego Flores de Valdés surrendered the galleon “Nuestra Señora del Rosario” to the English privateer without giving any resistance.

The “Contraarmada”, Drake’s Greatest Failure

After the disaster of the Spanish Armada in 1588, Elizabeth I of England ordered Drake to launch a counterattack against Spain, known as “Contraarmada”, which curiously had a fate as tragic as its Spanish predecessor. The adventure of the English squadron ended in an irreparable disaster. The first objective was La Coruña, which housed some surviving ships of the Spanish Armada, still under repair. Despite the English taking control of part of the city, the heroic performance of the militia, including the popular Maria Pita, forced the foreigners to flee without obtaining any loot.

Drake and his fleet – made up of more than a hundred ships of different sizes – headed to Lisbon with the intention of provoking a Portuguese uprising against the Spaniards. The landing of nearly 10,000 men to “liberate” Lisbon was initially a success, even though epidemics were already beginning to spread among the Anglo-Dutch troops. However, Drake’s army’s grinding strategies during his march to the vicinity of Lisbon and the brilliant performance of Alonso de Bazán – brother of the renowned sailor – at the head of a galleys’ squadron, made it impossible for the Portuguese capital to be surrendered. On the contrary, on June 16th, as the situation of the English army was already unmanageable, Drake ordered the retreat, which was followed by stifling persecution by Spanish-Portuguese forces. The rest of the campaign, which moved the action to the Azores Islands, only served to extend the agony of an expedition that, according to the British historian M. S. Hume, cost the death or desertion of 75% of the 18,000 men who originally formed the fleet.

Sir Francis Drake, after such failure, was disqualified from commanding any naval expedition for the next six years. His chance to redeem his trust came when the English queen, tired of having harvested nothing but defeats since 1588, recovered her trust in him around 1595. The goal was, again, the Caribbean. However, the Royal squad for this mission – mostly composed of volunteers – was placed under shared command, as the confidence in Drake’s leadership remained quarantined. John Hawkins – quite old for duty and in bad terms with Drake since Veracruz’s failure – was the other Admiral designated for the mission.

Disaster in the Caribbean: Spain learns from its mistakes

The expedition could not begin any worse. Against Hawkins’ opinion, Drake ordered to attack the Canary Islands and stock up there before heading to the Caribbean. The English pirate planned to take Las Palmas – barely defended by 1,000 men, mostly civilians – within four hours, but the defenders rejected easily the first attempt of landing. With 40 deaths and numerous wounded men, the English squad considered it useless to spend more soldiers on something that was supposed to be simple, but it wasn’t. The capture of an English captain during the encounter revealed the British intentions and allowed the Spanish authorities on the other side of the Atlantic Ocean to be warned.

When Drake’s fleet made an appearance in Puerto Rico, the defenders welcomed the privateer with a row made of five frigates – recently built and adapted to the Atlantic scenario – pointing their cannons at the outsiders. The invading fleet had to retreat momentarily when the Spanish cannons penetrated Drake’s own chamber just as Drake was toasting with his officers. The head of the fleet was unharmed, but two officers died, and many others were seriously injured. In addition, John Hawkins’ health was completely consumed shortly before this early welcoming, leaving Drake as the only commander.

Despite the furious reception, the English did not give up and launched a massive landing with barges on the night of the 23rd. Drake ordered to silently approach the frigates, which remained as the port’s guardians, to burn them one by one with incendiary artifacts. Far from destroying the Spanish ships, only one was burnt, but the fire ignited up the night making it easier for defenders to fight back the landing. The night ended with 400 men killed on the British side.

In addition to the new frigates intended to fight precisely against pirate attacks, the Spaniards had learned from their defensive mistakes. When Drake finally decided to move away from Puerto Rico – after passing through two small towns, Río del Hacha and Santa Marta, which brought him a little loot – he had to discard attacking Cartagena de Indias when he saw the imposing defenses that the city now had. The target, therefore, moved to Panama, where he ordered a double attack, by land and sea, which had a similar outcome to what happened in Lisbon seven years ago. Baskerville, in front of 900 soldiers, made his way ashore to the vicinity of Panama. Along the way he stumbled upon a small redoubt, the San Pablo, garrisoned by 70 men under the command of Juan Enríquez, who prevented the English advance twice. When another 50 men arrived to reinforce the garrison, Baskerville decided to retreat. The persecution, counting the dead, wounded, and prisoners, ended up with 400 casualties among the English.

Demoralized, exhausted, and sick with bleeding dysentery, Francis Drake unsuccessfully sought out oter potential preys. On January 27th, when the fleet was anchored at Portobelo’s entrance, Drake asked to have his armor so he could “die like a soldier”. He died the next morning and his body was thrown to the sea in a lead coffin against his will to be buried on dry land. Still, with barely no time for grieving his death, two of his heirs, his brother Thomas, and his nephew Jonas Bodenham, fought in the very ship to take ownership of the pirate’s belongings.

His last legacy, the disastrous ongoing expedition, still faced another tough test: the journey back to Europe. In the end, only eight of the initial 28 ships and one third of the men returned back to England.