Only 1,600 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 the winter sun, and a significant number of people of Jamaican origin have settled in and around Philadelphia.
But their historical and cultural trajectories seem vastly different, except for an unlikely family connection: Both histories were irrevocably altered by the actions of two men, father and son, who shared the same name: William Penn.
William Penn Jr., a Quaker, pacifist, and supporter of religious freedom, founded the Philadelphia Colony, which would later become the state of Pennsylvania, in 1682 under British colonial rule. The Philadelphia Colony played a key role in the work of America’s Founding Fathers, the Revolutionary War, and subsequent independence.
Penn is memorialized in a state, a top university, and a brand of breakfast oatmeal, and although his reputation is not unsullied (partly because of his stance on slavery), he is remembered for his principled struggle against London’s religious and political establishment.
Penn Sr. was less of a man of distinction than his son, but he left an equally enduring legacy in Jamaica, if only almost by accident: he was born in Bristol in 1621 and was soon drawn to a naval career, serving as a rear admiral for the anti-Parliamentary cause during the English Civil War.
However, in one notable episode in 1648, he was arrested but acquitted on suspicion of liaison with Charles I. He subsequently served as a vice-admiral in the First Anglo-Dutch War of 1652–1654.
However, in early 1654, his Royalist sympathies appear to have resurfaced when he is said to have offered to hand over the fleet he commanded to the exiled Charles II (Charles I had been executed in 1649).
Despite these signs of disloyalty, Oliver Cromwell, who oversaw the execution of Charles I, seemed to see Penn as a suitable candidate to lead the “Western Plan,” a bold plan to attack the economic and strategic power of Catholic Spain’s first occupant in the Americas, the Caribbean territory of Santo Domingo (now the Dominican Republic).
The Protector believed that by cutting off the trade routes of the Spanish Empire and weakening it, Charles II would be less likely to claim the throne with Spanish support. He also believed that acquiring additional colonies in the Caribbean (Barbados and four smaller islands were already in English hands) would serve as a distant base for sending political dissidents. The Protector appointed Admiral Penn as his commander-in-chief on August 18, 1654, 370 years ago.
Cromwell also decided to share Penn’s command of the expedition with General Robert Venables, a loyal army veteran, and to be assisted by two civil administrators.
It was a decision Cromwell would later regret, but it also suggests that he had doubts about Admiral Penn’s reliability.
TThe expedition of 38 ships and 2,500 poorly trained soldiers set sail in December of that year, spent two months forcibly recruiting an additional 3,500 soldiers in Barbados, and then, on April 13, 1655, approached Santo Domingo and the French island of Hispaniola.
Unfortunately for Penn and Venables, the Spanish were fully aware of their intentions (having been warned by Royalist spies) and were sending reinforcements from the South American mainland. Part of Venables’ force landed, marched through hot, mosquito-infested terrain, was ambushed by Spanish guerrillas, and was quickly routed.
Penn remained on board, but reluctantly agreed to evacuate the demoralized survivors, whom Venables himself mocked as “a bunch of scoundrels”. By this time the two men were barely on speaking terms.
It was a fiasco, but both commanders agreed on one thing: they did not want to return empty-handed to England and to the ruthless Cromwell. If Santo Domingo was too well-defended, Venables thought, why not try their luck 450 miles to the west on a tiny island the Spanish knew as Santiago (now Jamaica).
The territory was formally ceded from Spain to England in the Treaty of Madrid in 1670, and for over 150 years it became one of the Caribbean’s most profitable sugar-producing colonies.
Penn protested against the plan, but was ignored. A week later, on May 9, the British fleet arrived off the coast of Jamaica, and ten days later the outnumbered Spanish garrison surrendered to the same forces that had fled Santo Domingo.
While the first goal was unexpectedly difficult to achieve, the second was surprisingly easy: the Spanish governor resisted, but with few resources at their disposal, the Spanish colonists decided to free the slaves, who quickly fled into the rugged mountains of Jamaica.
Thus began Jamaica’s long colonial relationship with Britain (and later Great Britain), which formally ended with Jamaica’s independence on August 6, 1962.
The first English settlers were plagued by disease, food shortages, and occasional attacks from the Spanish and former slaves who refused to leave the island.
However, the feared counter-invasion never materialized, and Britain gradually increased its economic and military presence in Jamaica, which was formally ceded to Britain by Spain in the Treaty of Madrid in 1670, and which became one of the Caribbean’s most profitable sugar-producing colonies for over 150 years.
aThe rival careers of Venables and Penn took different directions. Penn set sail for England in June 1655, hoping to reach the country before his rival, but both were arrested for desertion and imprisoned in the Tower of London.
According to Cromwell, they had not received orders to return to London and the mission was a failure. They were soon released, but Venables’ military career was over; he retired to his Cheshire mansion and wrote a best-selling book on fishing.
William Penn Sr. remained in public life, being elected Member of Parliament for Weymouth in 1660, and attending Charles II’s return to England that same year. Having served under Cromwell as Lord Protector, he was a favoured supporter of the Restoration and worked hard to ingratiate himself with the new government. He was also very wealthy, lending large sums of money to Charles II.
His London neighbour, the diarist Samuel Pepys, was clearly not a big fan of him. He called the retired admiral a “hypocrite.” At one time they worked in the same Navy Board office, and Pepys wrote in his diary on 5 April 1666 that “the hypocrisy and impudence of Sir W. Penn to an office which is almost enough to make one mad to think of.”
Admiral Penn died in September 1670, the same year his son was arrested in London for “unlawful assembly” – William Penn Jr. had preached to crowds at Quaker street meetings, unlawfully challenging the supremacy of the Church of England.
He was eventually released and traveled to America seven years later, where he settled in a wooded area near New Jersey that he named Sylvania. The land had been given to him by King Charles II to settle his late father’s outstanding debts, but the King also insisted that the land be named Pennsylvania in his benefactor’s honor.
Ironically, the American state where Quakerism was founded was named in honor of the adventurous father, not the devout son, although William Penn strongly disapproved of his son’s religious extremism.
