Just under 1,600 miles apart, the US state of Pennsylvania and the Caribbean island of Jamaica might seem to have little in common. Some Pennsylvanians visit Jamaica for some winter sun, and a significant number of people of Jamaican descent have settled in and around Philadelphia.
However, their historical and cultural trajectories seem very different – except for an unlikely family connection. Both had their histories irrevocably altered by the activities of two men, father and son, who shared the same name: William Penn.
William Penn junior – a Quaker, pacifist and supporter of religious freedom – founded the colony of Philadelphia, later the Commonwealth of Pennsylvania, in 1682 during English colonial rule. It would play a key role in the activities of America’s founding fathers, the Revolutionary War, and the independence that followed.
Penn is commemorated in the name of the state, a top-ranked university and a brand of breakfast oats. And although his reputation is not intact (in part because of his stance on slavery), he is remembered for a principled fight against the religious and political establishment in London.
Penn senior was an altogether less admirable character than his son, but he would leave an equally lasting legacy in Jamaica – even if it was almost by accident. He was born in 1621 in Bristol and soon retired from a naval career, serving as rear admiral during the English Civil War on the side of the anti-monarchist Parliamentarians.
However, in a revealing episode in 1648, he was arrested on suspicion of having communicated with King Charles I, but acquitted. He then fought in the First Anglo-Dutch War of 1652–54, with the rank of vice-admiral.
But again his royalist sympathies seem to have emerged when, early in 1654, he is said to have offered to hand over the fleet he commanded to the exiled Charles II (Charles I was executed in 1649).
Despite such signs of disloyalty, it seems that Oliver Cromwell, who had overseen the execution of Charles I, saw Penn as a suitable candidate to lead his “Western Design” – a bold plan to attack economic and strategic power of Catholic Spain in its first possession. in the Americas: the Caribbean territory of Santo Domingo, today’s Dominican Republic.
The Lord Protector believed that weakening the Spanish Empire by disrupting its trade routes would reduce the chances of Charles II claiming the throne with Spanish help. He also thought that the acquisition of another colony in the Caribbean (Barbados and four smaller islands were already in British hands) would be useful as a remote location to which political dissidents could be sent. He appointed Admiral Penn as commander on August 18, 1654 – 370 years ago.
Cromwell also decided that Penn’s leadership of this expedition would be shared with General Robert Venables, a loyal army veteran, supported by two civilian administrators.
It was a decision Cromwell would later regret, but it also suggests that he had doubts about Admiral Penn’s credibility.
Tthat expedition—numbering 38 ships and 2,500 poorly trained troops—launched in December of that year. Two months were spent in Barbados forcibly recruiting another 3,500 men, before the task force approached the island of Hispaniola – which Santo Domingo shared with French Saint-Domingue – on 13 April 1655.
Unfortunately for Penn and Venables, the Spanish were fully aware of their intentions (warned by royal spies) and had brought reinforcements from the South American continent. Some of Venables’ troops were put ashore, marched through hot and mosquito-infested terrain, ambushed by Spanish guerrillas, and quickly routed.
Penn – who had remained on board his ship – reluctantly agreed to evacuate the demoralized survivors, derided by Venables himself as “an indecent mess”. By now the two men were barely speaking.
It was a fiasco, but both commanders agreed on one thing: that they were not willing to return to England – and to the unforgiving Cromwell – empty-handed. If Santo Domingo was very well defended, Venables reasoned, perhaps they could try their luck 450 miles to the west, on a smaller island known to the Spanish as Santiago (present-day Jamaica).
The territory was officially ceded by Spain to Britain in the 1670 Treaty of Madrid and, over 150 years, became one of the Caribbean’s most profitable sugar-producing colonies.
Penn was against the plan, but he was overruled. A week later, on May 9, the English fleet was off the coast of Jamaica, and 10 days later, the outnumbered Spanish garrison surrendered to the same troops that had fled Santo Domingo.
If the initial objective had proved unexpectedly difficult to achieve, the second was surprisingly easy. The Spanish governor offered little resistance, but he had few resources at his disposal, and the Spanish colonists decided to free their slaves—who promptly escaped into the impenetrable mountains of Jamaica.
Thus began England’s (and later Britain’s) long colonial relationship with Jamaica, which officially ended on August 6, 1962, with the island’s independence.
The first English colonists suffered from disease, food shortages and occasional attacks – both from the Spanish who had refused to leave the island and from the previously enslaved.
But a formidable counter-invasion never materialized and gradually the British built up their economic and military presence in Jamaica. The territory was formally ceded by Spain to Britain in the 1670 Treaty of Madrid and, over 150 years, became one of the Caribbean’s most profitable sugar-producing colonies.
orFor fighters Venables and Penn, their careers took different directions. Penn sailed for England in June 1655 – hoping to arrive before his competitor, who was hot on his heels. Both men were arrested, however – charged with desertion and imprisoned in the Tower of London.
According to Cromwell, they had no orders to return to London and had failed in their mission. They were soon released, but Venables’ military days were over. He retired to his Cheshire estate to write a successful book on fishing.
William Penn senior remained in public life, being elected member of parliament for Weymouth in 1660, and present at the return to England that year of Charles II. Having served under Cromwell’s Protectorate, he was more than happy to support the Restoration and was inclined to indulge the new regime. He was also very rich and lent a large sum of money to Charles II.
His neighbor in London – the diarist Samuel Pepys – was clearly not an admirer, referring to the retired admiral as “a false knave”. For a time, they worked in the same Marine Board office, and Pepys’ diary of April 5, 1666 says: “In the office, where Sir W. Pen’s lies and insolences would drive a man mad to think.”
Admiral Penn died in September 1670. This was the year his son was arrested in London for “unlawful assembly”. William Penn junior had preached to a crowd at a Quaker street meeting, thus illegally challenging the supremacy of the Church of England.
He was eventually released and seven years later sailed for America. There, he settled in a wooded area near New Jersey, which he named Sylvania. This land was given to him by Charles II in repayment of an outstanding loan owed to his late father. But the king also insisted that the land be named Pennsylvania in honor of his benefactor.
William Penn senior had strongly opposed his son’s radical religious views, and ironically it was in honor of the adventurous father rather than the devout son that the American state that acted as the cradle of Quakerism was named.
