Munro College Old Boys Association

Dr. Caleb Dickenson

Royal Connections 

The Reverend William Dickinson attended Eton College, a boy’s boarding school much like Munro, and then gained a Bachelor of Divinity from Oxford in 1619. His elder brother, Edmund, attended the same schools, but studied medicine, and in 1677, was appointed as one of the physicians to the Royal Household of King Charles II. He was confirmed as King’s Physician to James II in 1685 and held that position until James’ abdication in 1688. Edmund was thus first to bring fame to the family, but it was the offspring of William who were to bring fortune.  

The Consolation Prize 

In 1655, William’s son, Royal Navy Captain Francis Dickinson, joined the expedition led by Admiral Penn and General Venables to capture Hispaniola from the Spanish. The disorganized expedition failed miserably in its two attempts, and rather than return empty handed to face the wrath of Cromwell, Jamaica was identified as a consolation prize to save face. On May 10, 1655, therefore, young Dickenson was among a body of English soldiers who landed at Passage Fort in St. Catherine and marched on the capital, Santiago de la Vega. 

For his gallant conduct in the capture of Jamaica, Francis received from King Charles II, then conveniently a patient of his uncle Edmund, a land grant for some 6,000 acres in St. Elizabeth. This land included most of what is now Appleton Estate, named after the Appleton in south east England, where his father was Rector of the parish church. Rum production started at Appleton under the Dickinson family in 1749, but in 1845, the family cashed in and sold the estate. At this point, the family had struck it rich, but was to become even richer.  

Jamaican Roots 

Between travelling back and forth between England and Jamaica, and before becoming a member of the Jamaican Assembly from 1672 to 1673, Francis married into the Quaker family of Margaret Allen in 1662, and they had three sons, Johnathan, Jabez and Caleb. Little is known of Jabez, who probably stayed in England. The youngest son, Caleb, took charge of his father’s estates, which by the 1680’s had been expanded to over 10,000 acres.  

Johnathan, who was born in Jamaica in 1663, took over his father’s merchant business in Port Royal, where he and the business survived the 1692 earthquake, but still suffered great financial losses. Already one of the most successful traders with the American colonies, Johnathan left Jamaica in 1696 with the intention of extending the family business to Philadelphia. An apparent magnet for adventure, he survived shipwreck in Florida, losing his cargo of over £1,500, and also survived capture by native-American Indians, before being rescued by Spanish soldiers. After reaching Philadelphia, he wrote a journal about his adventures, which was published by the Society of Friends in 1699 and became an international best seller, reprinted 25 times in English, German, and Dutch.  

Politics and Plantations 

With the help of his brother Caleb in Jamaica, he then continued to be a successful merchant. From Port Royal, he shipped molasses, rum, sugar, spices, mahogany, and other tropical woods, all of which he sold at handsome profits, and from Philadelphia he brought flour, bread, deerskin, tobacco, and beer. His success not only restored and expanded his family’s fortunes in Jamaica, but quickly made him one of the richest men in Philadelphia. He was active in politics and served as chief justice before twice serving as Mayor of Philadelphia, from 1712 to 1713 and again from 1717 to 1719. When he died in 1722, in addition to two plantations in Jamaica at Barton and Pepper in St. Elizabeth, he left behind close to 500 acres of real estate in Philadelphia, plus an estate in New Jersey.     

Slave Traders 

Caleb eventually moved back to England, where from a base in Bristol he became an active partner in the triangular slave trade, which saw sugar and rum shipped to Bristol, the profits used to buy manufactured goods, which were then used to barter for slaves in West Africa. These slaves were in turn sold to his fellow planters in the West Indies. The participation of the Dickinson family in the slave trade is ironic, since they were Quakers, and it was the Quakers who first turned against the injustice of slavery and became the driving force behind what was to become the abolitionist movement. Caleb died in 1728, leaving wealth in Bristol plus vast holdings in Jamaica, including the two estates inherited from his elder brother Johnathan. He also left behind daughter Sarah and three sons, Ezekiel, Vickris, and Caleb Junior. 


By British law at the time, one was forbidden from practicing a trade or craft without serving a period of apprenticeship, and after his father’s death, Caleb junior was apprenticed at age 16 in 1733 to a Bristol merchant for £200. The resourceful Caleb turned his apprenticeship to personal advantage by marrying the merchant’s daughter in 1738. He was later to take over his father-in-law’s business after it went bankrupt in 1740. After his apprenticeship, Caleb remained in Bristol and became even more successful than his father. Between 1739 and 1748, he shared the ownership of two pirate ships with his younger brother Vickris and a group of other merchants, and along with his two brothers, he also oversaw the running of their numerous estates in St. Elizabeth. All three brothers became tremendously wealthy. 

Our Melting Pot 

None of the first three generations settled in the island and passed on direct supervision of the many Jamaican properties to their numerous children, but by then the melting pot that is Jamaica had already done its work. By 1781, and somewhat to the distress of some older members of the family, evidence of several coloured Dickinson children started showing up in the records of christenings, baptism records, and wills. It is somewhere at this point, that from this wealthy, illustrious, colourful, and by now bi-racial family, emerged our own Dr. Caleb Dickenson, to whom we largely owe the existence of Munro College.     

Our Caleb 

Our Caleb was a “gentleman of colour,” as was his uncle Robert Hugh Munro. In a context of a slave society where few persons of colour were elevated socially by the advantage of education or wealth, Caleb benefited from what seemed to be an almost unique feature of Jamaican society at the time, which did not exist in other slave societies, especially not in America. Despite the evils of slavery and a rigidly colour-coded society, it became the custom of several Jamaican plantation owners to not only acknowledge but take care of their coloured children. 

 In addition to sending them to England and Scotland for education, these children were in some cases also left substantial fortunes including vast holdings of real estate, and as both Munro and Dickenson did, became wealthy plantation owners and prominent citizens in their own right. Fearing the threat of a growing brown middle class, the Jamaican Assembly passed a law in December 1761 which made it illegal for any white person to leave inheritance in excess of £2,000 to any person of colour. Thankfully for Munro and Dickenson, and thankfully for Munro College, that law was unpopular, not always observed, and was formally overturned 1813.       

Caleb was sent to be educated in Catterick, Yorkshire, and studied medicine. He returned to practice in St. Andrew and St. Thomas, and spent the evening of his years at his Knockpatrick estate in south Manchester, which he had inherited from his uncle Robert Hugh Munro. He died on 21st January 1821, and was buried there, earning an obituary in the Royal Gazette which prophetically ends: “…..his benevolence and charity have been the highest ornaments of his character, as they will remain the most lasting of his name.” 

His Homecoming 

In 1931, his remains were brought from Knockpatrick to Munro, where they lie under the floor of the chapel. In a moving ceremony, Munro boys and upper school girls of Hampton, members of staff of both schools, Headmaster Harrison, along with then closest living relative, Dr. W.N. Dickenson, led a procession from Top Gate to the Chapel, where he was re-interred to the strains of the Hampton girls singing, “Except the Lord build the house, they labour in vain that build it.”  

The Bequest 

During his lifetime, Caleb Dickenson was the recipient of a bequest of his late uncle, Robert Hugh Munro, who willed his real and personal estate to Dickenson and the Churchwardens of St. Elizabeth to establish a school for the poor children of the parish. Dickenson, who became even wealthier than Munro, enlarged the funds, and left by his will of 1821 funds to establish the school and to also support the aged poor of St. Elizabeth. At the time of his death, his legacy included cash of £26,000 in England, majority shares in a fine ship, Knockpatrick plantation in Manchester, and the Grosmond, Maggotty Pen, and Middlesex Pen estates in St. Elizabeth. 

Unfortunately, as had been the case with his uncle’s estate, his wishes were not carried out for some time, and records indicate that no less than the then Governor of Jamaica, the Attorney General, and the Duke of Manchester, all had a dip into the money destined for Munro College and Hampton, before it was finally rescued in 1855. 

For his fascinating link to Jamaica’s colourful history, his faithfulness to his uncle’s dream, his enhancement of the means for its realization, and for his big heart of charity, Dr. Caleb Dickenson was gratefully inducted into the Munro College Old Boys Association Hall of Fame. 

Posted on: June 2nd, 2021