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Simon Fernandes
Born c. 1538
Terceira, the Azores
Died c. 1590 (aged c. 52)
unknown, possibly the Azores
Piratical career
Nickname The Swine
Allegiance  Portuguese Empire
 Spain
 England
Years active 1570s-c.1590
Rank Captain
Base of operations South Wales, England
Battles/wars Spanish Armada
Later work Piloted Sir Walter Raleigh's failed 1587 expedition to Roanoke island, "The Lost Colony"

Simon Fernandes (Portuguese: Simão Fernandes; born around 1538 – died around 1590) was a skilled sailor and navigator from Portugal. He lived in the 1500s. He helped English explorers try to start colonies in America. These trips included the 1585 and 1587 expeditions to Roanoke Island, which is now part of North Carolina. Back then, this area was called Virginia.

Fernandes learned how to navigate in Spain. He trained at a famous school called the Casa de Contratación in Seville. Later, he became a pirate and attacked Spanish ships. In 1577, he was caught for piracy. But Sir Francis Walsingham, a powerful English official, saved him. Fernandes then became a supporter of England and Queen Elizabeth I.

In 1578, Fernandes started working for Sir Humphrey Gilbert. Later, he worked for Sir Walter Raleigh. He was the pilot for the 1587 trip to Roanoke. This journey is famous for the "Lost Colony" because the settlers disappeared. Fernandes likely died around 1590 during a sea journey to the Azores. A copy of one of his maps of North America still exists today. It helped John Dee create a map in 1580 that supported England's claims to the land.

Early Life and Training

Simon Fernandes was born around 1538. He was from Terceira Island in the Azores, a group of islands belonging to Portugal.

He received his training as a navigator in Spain. He attended the well-known Casa de Contratación pilot school in Seville. He even sailed across the Atlantic Ocean at least once for the Spanish King.

Career as a Sailor

Becoming a Pirate

Sir Francis Walsingham by John De Critz the Elder
Sir Francis Walsingham helped Fernandes avoid punishment.

At some point, Fernandes stopped being loyal to Spain. In the 1570s, he started a new life as a pirate. He operated from South Wales with another famous pirate, John Callis. They attacked Spanish ships. Even though England was officially at peace with Spain, Queen Elizabeth I of England often ignored such actions.

However, the Portuguese ambassador, Francisco Giraldi, complained strongly about Fernandes. This was after seven Portuguese sailors were reportedly killed. In 1577, Fernandes, then 39, was arrested in Cardiff. He was taken to London to face trial.

Instead of being executed, Fernandes was set free. It seems Queen Elizabeth's spymaster, Sir Francis Walsingham, helped him. Walsingham likely saw that Fernandes could be very useful. He knew a lot about challenging Spain's control over trade in the New World. The ambassador, Giraldi, blamed Walsingham for Fernandes's release. Fernandes had more experience navigating the West Indies than almost anyone in England. This made him a valuable asset for England's early voyages to the Americas.

Working as a Navigator

SirGilbertHumphrey
Fernandes' boss, Sir Humphrey Gilbert, around 1583.
Roanoke map 1584
A watercolor map of the Roanoke area from around 1585, by Governor John White.

In 1578, Fernandes became the pilot for Sir Humphrey Gilbert. Gilbert was planning a trip to start a colony in the Americas. Walsingham supported this plan. The Spanish authorities knew Fernandes well and did not approve of his new activities. In 1578, the Spanish Ambassador wrote to King Philip II of Spain. He mentioned Gilbert's planned voyage:

"They are taking with them one Simon Fernandes, a Portuguese, a thorough-paced scoundrel, who has given and is giving them much information about that coast, which he knows very well."

In 1580, Gilbert sailed to America in his ship, the Squirrel. Fernandes was the pilot. They crossed the Atlantic very quickly. He was a very skilled navigator. He had been trained by Thomas Harriot in the newest navigation methods.

During the trip, Fernandes surprised the ship's chaplain, Richard Madox. Fernandes said he was "at war with the King of Spain." When asked how this was possible, since England was at peace with Spain, Fernandes replied that he had "a free pardon from five Privy Councillors for carrying on the war with Spain."

In 1583, Sir Humphrey Gilbert drowned while returning from Newfoundland. Fernandes then started working for Sir Walter Raleigh. Raleigh had taken over Gilbert's plans for exploring Virginia.

Fernandes was a great sailor, but he was not very popular with his shipmates. He was the master and chief pilot for Raleigh's 1585 trip to Roanoke. Sir Richard Grenville led this expedition. Fernandes returned to England later that year. During the voyage, his shipmates called him "the swine." Perhaps they did not like a foreigner being in such an important position.

The Lost Colony Expedition

Sir Walter Raleigh
Fernandes' boss, Sir Walter Raleigh.
Coat of Arms of Simon Ferdinando
Coat of Arms of Simon Fernandes.

In May 1587, Fernandes piloted a new expedition. This group of settlers was led by Governor John White. They sailed for Virginia in a ship called The Lion. This time, White's group included women and children. They hoped to build a lasting colony in Virginia. White and Fernandes did not get along. White's diary shows their arguments. White accused Fernandes of harming the settlers' plans. For example, he said Fernandes abandoned the expedition's small boat, called a flyboat.

In 1587, the settlers wanted to go to Chesapeake Bay, not Roanoke. But when they reached Roanoke in late July, Fernandes refused to let White's men get back on the ship. White wrote in his diary that Fernandes's helper told the sailors "not to bring any of the planters back againe, but leave them on the island." White seemed to give in to his navigator's actions. Fernandes said that "summer was farre spent," meaning it was too late in the year. So, he would only land the settlers there. It is not clear why Fernandes landed them in the wrong place. He and his crew might have wanted to return to the West Indies. There, they could attack Spanish ships for profit.

If Governor White's diary is true, Fernandes's actions may have led to the sad outcome of the settlement. This is known as the "Lost Colony" because the settlers disappeared. Some historians think Fernandes might have even tried to ruin the whole plan. However, his reasons for doing so are still unknown.

Fernandes did not take part in any more trips across the Atlantic after this. But he did fight in the battle against the Spanish Armada. He disappears from records after 1590. He sailed with an English fleet to the Azores. He most likely did not survive that journey.

Legacy

A copy of one of Fernandes's maps of the East coast of North America still exists. It is in the Cotton Collection. This map was likely a main source for John Dee's 1580 map. Dee prepared his map for the Queen. It was used to support England's claims to all of North America north of Florida.

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