As the Middle Ages transitioned into the Renaissance, the county of Portugal located on the Atlantic coast in the Kingdom of León-Castilla was poised to play a significant role in world events. How did this county that was not even a kingdom rise to become the dominant world power?

Whatever might be said about Christopher Columbus and his impact on the New World, he was an excellent dead-reckoning navigator, and his (in)famous voyage changed the course of Western history.

In America they’re best known as Ferdinand and Isabella, who sponsored Christopher Columbus’s journey to the New World; but in Iberia they’re Los Reyes Católicos, the Catholic King and Queen, who drove the Moors and Jews out of what was to become Spain.

Western Europe passed from the Middle Ages into the Renaissance and the Age of Exploration (Age of Discovery) in the fifteenth century. Under the leadership of Prince Henry the navigator, the kingdom of Portugal, a seafaring nation located on the southwest corner of the Iberian Peninsula, began exploring west into the Atlantic and south down the west coast of Africa. Iberia continued to be a strong force in the Caribbean for the next hundred years.

British forces took Jamaica from the Spanish in 1655, when Oliver Cromwell sent an expedition to acquire new colonies in the Americas, establishing it as a vital port and center of trade for the British government. This post traces the British succession from the Wars of the Roses to the English Civil War and explores how the history of the Caribbean might have been different had Henry VIII’s older brother, Arthur Tudor, lived to reign as King of England.

Captain Hornigold and the Pirate Republic is about an English sailor who finds himself stuck in Jamaica after a war with nothing to do. But why the Caribbean? What drew pirates to this out of the way location?

This post traces how the quest for a luxury item, a spice such as a peppercorn, evolved into sugar plantations and silver mines. The mines produced the pieces of eight that were a natural draw for pirates. And the West Indies (the Caribbean and the Bahamas) was ideal for the single-masted sloops that could hide in the many coves and cays and their surrounding islands.

Nature created a perfect playground for the Caribbean pirates. Silver was mined, smelted and pounded into pieces of eight near where the silver was mined, Bolivia, Peru, and Mexico, and shipped to Spain from the ports at Cartagena, Colombia, Porto Bello, Panama, and Vera Cruz, Mexico. The trade routes followed the wind and the current up along the coast and through the Florida Straits, the Windward Passage and the Mona Passage.

But the Caribbean is a big place, 1.063 million square miles, and the vessels were sail driven, powered by the wind and the current. If a vessel could sail at 4 knots an hour, it could sail 100 nautical miles in a day. Nassau to Cartagena is about 1183 nautical miles, or 12 days one way. Nassau to Port Royal is 670 nautical miles, or 7 days.

Therefore, sailing time must be factored in when reading old records that place a pirate vessel at point A on … day and at point B on … day.

Willie Sutton, a famous American bank robber, when once asked why he robbed banks responded, “because that’s where the money is.” Pirates in the Caribbean in the early 1700s felt the same about Spanish ships carrying silver from the Americas to the king’s treasury in Spain.

In addition to the reward, the shape of the Caribbean was perfect. The silver was coming from ports of Cartagena, Porto Bello, and Vera Cruz along the coast of Spanish America. The trade routes would force the Spanish vessels through the narrows of the Florida Straits, the Windward Passage, or the Mona Passage. All the pirates needed were safe havens and the Caribbean had plenty of those. But could a safe haven also become a pirate republic?

Was the life of a pirate in the Caribbean in the early 1700s glamorous? Judge for yourself as you follow Benjamin Hornigold after the Queen Anne’s War. He, as many other privateers and Royal Navy men, found himself in Port Royal, Jamaica, a city that was once described as the Sodom and Gomorrah of the West Indies. Now, in 1713, Port Royal was only a shadow of its past.

Hornigold moved to Nassau, began his life as a pirate and became the leader of the non-Jacobite faction in the Pirate Republic. He sailed with the French pirate Olivier LeVasseur and the British pirates Sam Bellamy, Paulsgrave Williams, Edward Thache (aka Blackbeard), Major Stede Bonnet and Captain Napping (who lacked a first name).

Upon the arrival of the new governor of the Bahamas, Woodes Rogers, Hornigold accepted the King’s pardon and became a pirate hunter.

Edward Thache (named Blackbeard by the press) was active as a pirate, or at least the earliest records to date show, from late 1716 until his death in late 1718. Benjamin Hornigold was active as a pirate from mid 1713 through 1717. Seldom did their paths cross and when they were together, it was not for very long.

This post traces their paths and presents the argument “peer, not protege.”

If you were a pirate sailing in the Caribbean and your quartermaster just handed you some pieces of eight, your share from the last seized vessel, would you be curious as to what you were given? Being British, your benchmark was the English pound sterling (crowns, shillings, and pence). Naturally, the bottom line was buying power. Would your pieces of eight have the same buying power as one, two, or three English pounds? Would your piece of eight have the same buying power whether you were in Port Royal, Nassau, Charles Town, New York or Boston?

On July 24, 1715, a Spanish plate fleet, eleven Spanish vessels and a French escort, sailed from Havana for Spain. Philip V, the king of Spain, was in dire need of the cargo—two years of silver. A week later, all eleven Spanish vessels were caught in a hurricane and wrecked off the Florida coast. The total cargo was estimated to be 65,000,000 pieces of eight. The Spanish began salvage and set up storehouses near each wreck site.

The day after Christmas, 1715, Henry Jennings and John Wills, who had sailed from Port Royal, Jamaica, to the Florida storehouses, drove away the Spanish guards and made off with 350,000 pieces of eight.

Caribbean pirates were democratic and would divide plunder—one-third for the owners of their sloops and two-thirds for their captains and crew. A rough calculation shows that only eleven percent of the plunder was distributed to the captains and crew.

What happened to the remaining 64,000 pounds?

Our story takes us back to the beginning of the Tudor monarchy. Under male-primogeniture, succession to the throne would appear straightforward but the history of royal succession under the Tudors and Stuarts was not always so. Religion and politics often played a role and therefore it becomes important to the question of who becomes the monarch of England, Scotland and Ireland, if James Stuart, the Duke of York, was not available to succeed his brother Charles II in 1685.