The Penn connection | On this day

The life and accomplishments of William Penn Jr are well documented. But his father’s (controversial) exploits are much less so, and had a significant impact on British colonial ambitions in the Caribbean, writes James Ferguson

  • A painting depicts the arrival of William Penn, Jr in what would become Pennsylvania. Niday Picture Library/Alamy Stock Photo
  • Portrait of William Penn, Sr. Wikimedia Commons

Just under 1600 miles apart, the American 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 sizable number of people of Jamaican origin have settled in and around Philadelphia.

Yet their historical and cultural trajectories seem largely different — except for an unlikely family connection. Both had their histories irreversibly 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 ensuing independence.

Penn is commemorated in the state’s name, a top-ranking university, and a brand of breakfast oats. And although his reputation is not untarnished (partly because of his attitude towards slavery), he is remembered for a principled struggle against the religious and political establishment in London.

Penn senior was an altogether less admirable character than his son, but he was to leave an equally lasting legacy in Jamaica — even if it happened almost by accident. He was born in 1621 in Bristol, and was quickly attracted to a naval career, serving as a rear admiral during the English Civil War on the side of the anti-monarchist Parliamentarians.

In a revealing episode in 1648, however, he was arrested on suspicion of communicating with King Charles I, but was exonerated. 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 surfaced when, early in 1654, he is said to have offered to turn the fleet he commanded over to the exiled Charles II (Charles I having been executed in 1649).

Despite such signs of disloyalty, it appears that Oliver Cromwell, who had overseen Charles I’s execution, saw Penn as a suitable candidate to lead his “Western Design” — an audacious plan to attack the 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 assistance. He also thought that the acquisition of a further colony in the Caribbean (Barbados and four smaller islands were already in English hands) would be useful as a faraway place to which political dissidents could be sent. He appointed Admiral Penn as commander on 18 August, 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 that Cromwell would later regret, but it also suggests that he harboured doubts over the reliability of Admiral Penn.


The expedition — numbering 38 ships and 2,500 poorly trained troops — set sail in December that year. Two months were spent in Barbados forcibly recruiting a further 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 entirely aware of their intentions (alerted by royalist spies), and had brought in reinforcements from the South American mainland. Some of Venables’ troops were taken ashore, marched through hot and mosquito-ridden terrain, ambushed by Spanish guerrillas, and quickly routed.

Penn — who had remained aboard his ship — reluctantly agreed to evacuate the demoralised survivors, derided by Venables himself as “a rascally rabble”. By now the two men were barely on speaking terms.

It was a fiasco, but both commanders agreed on one thing: that they were unwilling to return to England — and to the unforgiving Cromwell — empty handed. If Santo Domingo was too well defended, Venables reasoned, perhaps they could try their luck 450 miles to the west, in 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 opposed to the plan, but he was ignored. A week later, on 9 May, the English fleet was off the coast of Jamaica, and 10 days later the outnumbered Spanish garrison surrendered to the same troops who had fled from Santo Domingo.

If the original target had proved unexpectedly difficult to achieve, the second was surprisingly easy. The Spanish governor offered some resistance, but he had few resources at his disposal, and the Spanish colonists decided to free their slaves — who promptly escaped into Jamaica’s impenetrable mountains.

So began England’s (and then Britain’s) long colonial relationship with Jamaica, which formally ended on 6 August, 1962, with the island’s independence.

The first English colonists suffered from disease, food shortages, and occasional attacks — both from Spaniards who had refused to leave the island and from the formerly enslaved.

But a feared counter-invasion never materialised, and gradually the British built up their economic and military presence in 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.


As for the warring Venables and Penn, their careers took differing directions. Penn sailed for England in June 1655 — hoping to arrive before his competitor, who was hot on his heels. Both men were arrested, though — accused of desertion, and confined 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 estate in Cheshire to write a successful book on angling.

William Penn senior remained in public life, being elected as a 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 happier to support the Restoration and was keen to ingratiate himself with the new regime. He was also very wealthy, and lent a large sum of money to Charles II.

His neighbour in London — the diarist Samuel Pepys — was obviously not an admirer, referring to the retired admiral as “a false knave”. For a time, they worked in the same Naval Board office, and Pepys’ 5 April, 1666 diary reads: “To the office, where the falsenesse and impertinencies of Sir W. Pen would make a man mad to think of.”

Admiral Penn died in September 1670. This was the year that his son was arrested in London for “unlawful assemble”. William Penn junior had been preaching to a crowd at a Quaker street meeting, thereby illegally challenging the supremacy of the Church of England.

He was eventually released, and seven years later sailed to America. There, he settled in a forested area near New Jersey which he called Sylvania. This land was granted to him by Charles II in settlement of the unpaid loan owing to his late father. But the king also insisted that the land be named Pennsylvania in honour of his benefactor.

William Penn senior had strongly disapproved of his son’s radical religious views, and ironically it was in honour of the adventuring father rather than the devout son that the American state that acted as the cradle of Quakerism was named. 

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