Port Royal Kingston Jamaica

Columbus sights Jamaica on May 4, 1494, circumnavigates the island, and returns to Isabela after five months of explorations.

Smuggling is rampant in the Spanish American empire, and the smugglers of the Caribbean eventually become a semi-organized navy of buccaneers, an international brotherhood of privateers.

The buccaneers, operating under French patronage from their base on Tortuga, move to Port Royal upon England’s capture of Jamaica.

This era sees the wholesale introduction of a slavery-based plantation economy in Jamaica, which, under English rule, has become a haven of privateers, buccaneers, and occasionally outright pirates: Christopher Myngs, Edward Mansvelt, and most famously, Henry Morgan, who raids up and down the Spanish Main with buccaneers from all over the Caribbean.

Large buccaneer attacks on Spanish settlements, secretly condoned by the English authorities, will continue till the end of the century, gradually laying waste to the entire region.

Jamaica’s population in 1660 is about forty-five hundred whites and some fifteen hundred blacks.

General-at-Sea William Penn and General Robert Venables had seized Jamaica in 1655 without orders in the name of Britain's Lord Protector Oliver Cromwell, seeking to make up for the disastrous failure of the mission Cromwell had assigned them: to seize Hispaniola.

Spanish resistance has continued for some years, in some cases with the help of the maroons, but Spain will ever succeed in retaking the island.

Under English rule Jamaica has become a haven of privateers, buccaneers, and occasionally outright pirates: Christopher Myngs, Edward Mansvelt, and most famously, Henry Morgan.

Myngs had earned a reputation for unnecessary cruelty during his actions as a commerce raider during the Anglo-Spanish War of 1654, sacking and massacring entire towns in command of whole fleets of buccaneers.

The Spanish government considers Myngs a common pirate and mass murderer, protesting to no avail to the Cromwell government about his conduct.

Because he had shared half of the bounty of his 1659 raid on Venezuela, about a quarter of a million pounds, with the buccaneers against the explicit orders of Edward D'Oyley, the English Commander of Jamaica, he had been arrested for embezzlement and sent back to England on the Marston Moor in 1660.

The later governor described him in an accompanying letter as "unhinged and out of tune".

The Restoration government has retained Myngs in his command however, and in August 1662 he is sent to Jamaica commanding the Centurion in order to resume his activities, despite the fact the war with Spain had ended.

This is part of a covert English policy to undermine the Spanish dominion of the area, by destroying as much as possible of the infrastructure.

Myngs decides that the best way to accomplish this is to employ the full potential of the buccaneers by promising them the opportunity for unbridled plunder and rapine.

He has the complete support of the new governor, Lord Windsor, who fires a large contingent of soldiers to fill Myngs's ranks with disgruntled men.

This year, ...

The Crown in November 1662 relieves Lord Windsor, who has refused to stop the pirates from attacking Spanish ships, and appoints his deputy, Brigadier General Charles Lyttelton, as acting governor of Jamaica.

Myngs’s atrocities lead to an outrage and Charles II of England is forced to forbid further attacks in April, a policy to be carried out by Jamaica’s new acting governor, Thomas Lynch.

Nevertheless, a pattern has been set and large buccaneer attacks on Spanish settlements, secretly condoned by the English authorities, will continue till the end of the century, gradually laying waste to the entire region.

Thomas Modyford arrives in Jamaica on June 4, 1664, with seven hundred planters and their slaves, marking the wholesale introduction of a slavery-based plantation economy in Jamaica.

He appoints to his council his brother, Colonel Sir James Modyford.

Robert Searle’s first known ship was the sixty-ton, eight-gun Cagway, the largest of three Spanish merchantmen captured by Christopher Myngs as he returned from his raid on Santa Marta and Tolú (Colombia) in 1659.

Searle had captained the Cagway four years later as part of Myng’s expedition against Santiago de Cuba.

The political situation in Europe and the Caribbean is volatile in 1664.

Constant raiding by English buccaneers has prompted repeated and vociferous protests from Madrid, delivered by the Spanish ambassador to King Charles II of England.

In turn, a letter to Governor Modyford from the king stated that “His Majesty cannot sufficiently express his dissatisfaction at the daily complaints of violence and depredation” against the Spanish by the ships of Jamaica.

Modyford is “again strictly commanded not only to forbid the prosecution of such violence for the future, but to inflict condign punishment upon offenders, and to have the entire restitution and satisfaction made to the sufferers.” This letter, signed in London eleven days after Modyford first landed at Port Royal, in early June, does not arrive until the beginning of September.

It causes something of a sensation on the island.

At this moment there are two rich Spanish prizes from Cuba at anchor in Port Royal’s harbor.

Both are heavily guarded and prizes to Searle, who has already landed the boxes and bags of Spanish coin so that the king’s share could be calculated.

Modyford promptly summons the Council of Jamaica and shows them the letter.

The alarmed Council decides that the governor of Cuba should be told at once that the captured ships and money are being returned.

It is resolved that “all persons making further attempts of violence upon the Spaniards be looked upon as pirates and rebels, and that Captain Searle’s commission be taken from him and his rudder and sails taken ashore for security.”

Jamaica’s newly installed Governor Thomas Modyford divides the island into parishes in late 1664, soon after his arrival from Barbados.

Sir James Modyford is granted a royal license in November to ship convicted felons from England to his brother in Jamaica, where Sir Thomas uses a labor force of twenty-eight English indentured servants.

As governor, Modyford is required to call in all pirates and privateers of the West Indies because England and Spain are temporarily at peace.

However, the majority of these buccaneers either refuse to return or do not receive the message that there has been a recall, including Henry Morgan, whose uncle, Edward Morgan, had preceded Modyford as acting governor of Jamaica in 1664.

Henry Morgan had married his uncle's daughter Mary, a cousin.

Richard Browne, who would serve as the pirate Morgan's surgeon at Panama, said that Morgan came to Jamaica in 1658 as a young man, and raised himself to "fame and fortune by his valour".

Although Modyford proclaims loyalty to the Crown, he is to become a critical element of Henry Morgan’s exhibitions by going against the word of the king and granting Morgan letters of marque to attack Spanish ships and settlements.

The Brethren or "Brethren of the Coast", a loose coalition of pirates and privateers commonly known as buccaneers and active in the Atlantic Ocean, Caribbean Sea and Gulf of Mexico, are a syndicate of captains with letters of marque and reprisal who regulate their privateering enterprises within the community of privateers and with their outside benefactors.

They are primarily private individual merchant mariners of Protestant background, usually of English and French origin.

During their heyday when the Thirty Years War was devastating the Protestant communities of France, Germany, and the Netherlands and England was engaged in various conflicts, the privateers of these nationalities had been issued letters of marque to raid Catholic French and Spanish shipping and territories.

Based primarily on the island of Tortuga off the coast of Haiti and in the city of Port Royal on the island of Jamaica, the original Brethren were mostly French Huguenot and British Protestants, but their ranks have been joined by other adventurers of various nationalities including Spaniards, and even African sailors, as well as escaped slaves and outlaws of various sovereigns.

In keeping with their Protestant and mostly Common Law heritage the Brethren are governed by codes of conduct that favor legislative decision-making, hierarchical command authority, individual rights, and equitable division of revenues.

Edward Mansfield, or Mansvelt, is at this time the acknowledged informal chieftain of the Brethren.

His background is largely obscure, with conflicting accounts as a Dutchman from Curaçao or an Englishman.

He is first recorded accepting a privateering commission from Governor Edward D'Oyley at Port Royal in 1659.

Based from Jamaica during the early 1660s, he had begun raiding Spanish shipping and coastal settlements traveling overland as far as the Pacific coast of South America.

He had in late 1665 attacked a Cuban village with two hundred buccaneers.

Soon after this raid, he is offered a commission by Modyford at Port Royal to sail against the Dutch at Curaçao.

His men refuse to fight the Dutch however, some themselves being Dutchmen, while others believe it will be far more lucrative to continue their raids against the Spanish.