Throughout history, there have been many figures that remained on the precipice of being completely forgotten or blatantly ignored. Diego, who lived during the Tudor Period (1485-1603 CE) is one of these figures. Unbeknownst to most, Diego was an escaped slave who played an important role in the success of Sir Francis Drake, the legendary English circumnavigator and privateer. Before his death in 1579 CE, Diego the Circumnavigator was on his way to being the first black man to circumnavigate the world.  Although Diego’s history is chequered at best, Diego’s impact did not go unnoticed by Drake and his fellow crewmen.

The Imprisonment of Diego the Circumnavigator

The majority of Diego’s history is attributed to Sir Francis Drake Revived, a book published in 1628 CE that is composed of manuscripts and logs from Drake’s raiding expedition presented to Elizabeth I in 1593 CE but Diego’s origins remain unclear. Before Drake and Diego crossed paths, Diego could have been taken from West Africa or born into enslavement within the Spanish territories of the Americas.

By 1640 CE, Portugal and Spain’s Iberian ports (Lisbon, Seville, and Cádiz) had contributed to 97% of European-based slave voyages. It is estimated that around 500,000 African captives were transported to Spanish America within that period. It wasn’t until 1543 CE, after Spain signed the Asiento de Negros agreements, that Spain permitted other nations to transport African slaves to Spanish territories. As a result, approximately 12 million African captives were transported over the Atlantic, 1 million of which did not survive the journey. Whether taken as a slave from West Africa or born into enslavement, Drake and his crew acknowledged Diego as an enslaved black man when they encountered him in Nombre de Dios, Panama.

Although it is now widely acknowledged as immoral, slavery was thought necessary for economic progress and expansion from the 16th through the 19th centuries. The majority of slaves, aside from a selected few, were transported to work on plantations in the New World that produced tobacco, sugar, rice, corn, and cotton. The slaves that did not find themselves working the plantations would face less hardship with duties such as cooking, cleaning, and caring for the children of their “owners.”

Although Portugal and Spain started the Transatlantic Slave Trade, slavery was not a new concept. Although a specific date is difficult to determine due to the practice having roots predating written history, slavery is believed to have come into existence after the Neolithic Revolution (10,000 BCE), when communities started to produce a high agricultural production and growing populations.

The oldest known evidence of slavery is the Mesopotamian Code of Hammurabi (1750 BCE) , which alluded to slavery as an established system in Sumeria. Eventually, slavery would spread to other areas of Mesopotamia, Greece, Ancient Egypt, Rome, and the Pontic-Caspian Steppes. With Portugal and Spain demonstrating the wealth they had collected and potential growth via the slave trade, it was only a matter of time before other nations sought huge labor forces through enslavement. It wasn’t until the early 17th century that race-based slavery became a concept as opposed to slaves being obtained from prisoners of war, debts, and inheriting the status from one’s parents during antiquity.

Diego’s Chance of Escape 

During Drake’s raid of Nombre de Dios in 1572 CE, Diego escaped the grasp of his capturers and made his way to Drake’s ship. Daringly rushing through gunfire and toward the English ships on shore, Diego was fired upon three times by the English ships and continued to press forward. At the time, England was regarded as a country of freedom, and Diego, likely hearing the commotion of the English raid, sought to seize the opportunity of freedom by joining the English.

It is unclear if Diego knew of Drake’s history in the slave trade. Prior to Drake’s raid of Nombre de Dios, Drake accompanied his cousin, John Hawkins, on his Trans-Atlantic Slave Trade expeditions between 1560 and 1568 CE. Drake would go on three slave voyages and become one of Britain’s earliest slave traders. Hawkins and Drake transported hundreds of slaves from the west coast of Africa to Rio de la Hacha and San Juan de Ulua. Following a traumatic ambush on the English by the Spanish that resulted in a large number of casualties and sunken ships, Drake would abandon slave trading in 1568 CE.

Despite the crew’s initial animosity, Diego was permitted to board the ship. Diego cautioned Drake’s crew that 150 Spanish troops were initially stationed in the town to protect against the Cimaroons (African people that had escaped Spanish imprisonment) and that the raid should be abandoned or the English would be oppressed by soldiers and townspeople. Diego was given a position on the crew, likely after appealing to Drake and the rest of the crew with his fortitude and resourcefulness. Additionally, Diego proved that his mastery of Spanish (and eventually English), and his familiarity with the region would be worthwhile to the ambitions of Drake.

The Nombre de Dios Heist and Freedom

Largely due in part to Diego and subsequent meetings with the Cimaroons, Drake was able to pull off the largest heist on Spanish-American treasure in history. In 1573 CE, Drake had learned of a 190-mule silver train that was en route to King Philip II’s treasury in Spain. Alongside the Cimaroons, French privateers led by Captain Le Tetu, and his crew, Drake were able to ambush the Spanish with minimum consequences.

However, after seizing 20 tonnes of silver and gold, the escape strategy became challenging. The heist was executed at night, and the crew had to transport the treasure 30 kilometers (18.6) miles over rugged terrain during a storm, the Spanish were after them, and the escape ships were pushed away from the rendezvous point. Following some improvised ingenuity, Drake and his men would eventually return and reclaim the wealth after burying a substantial quantity of treasure amid the undergrowth in holes. With the Spanish treasure and a number of Spanish vessels having been seized and looted, Diego traveled to Plymouth, England, accompanying Drake five months later.

Diego the Navigator: Circumnavigation and Death

Following four peaceful years in Plymouth, England, Diego would accompany Drake on an expedition to further terrorize Spanish settlements on the American Pacific Coast, a covert task commissioned by Queen Elizabeth I. As a paid crew member aboard the Golden Hinde, Diego served as an interpreter, guide, and camp builder. The expedition started off on the bad side of things with storms that forced Drake’s fleet to return and seek refuge in Falmouth Harbor for over a month. When they were able, the fleet set sail again, arriving near Morocco in December 1577 CE.

When the English fleet arrived on Africa’s west coast, things changed for the better. Drake and his crew assaulted, pillaged, and captured three Spanish and Portuguese ships. Following two months without sight of land while crossing the Atlantic, the fleet reached South America, but not without its additional hardships.

Drake would be plagued with a potential mutiny, a devastating storm, and the abandonment of three ships unfit for further voyage. Things would only take a turn for the worse. While on the way to the coast of Peru, Drake’s crew stopped on the Island of Mocha, near Chile, a territory inhabited by the Mapuche people in 1578 CE. According to the accounts of Sir Richard Hawkins, Drake’s crew were attacked by the Mapuche people and Diego was wounded twenty times in the process. Diego survived the incident, undoubtedly having suffered tremendously. It wasn’t until 1579 CE, near the Maluku Islands of Indonesia, that Diego would succumb to his wounds.

Although Diego died prematurely and did not complete the circumnavigation, he is a brilliant example of what a person of color could do amid a time of oppression. While Drake was the first Englishman to navigate the Straits of Magellan, Diego is undoubtedly the first free black man to go through them as well. When Drake discovered Tierra del Fuego was not another continent but islands, Diego was there as well. When Drake sailed further north along the coast of the Americas than any other European had, Diego was right there with him, becoming the first black man to do so.