# John Gregory (governor)

John Gregory (1688 - 1764) was a Jamaican-born colonial administrator, slave-owner, and military official in the eighteenth century British colony of Jamaica who acted as Governor of Jamaica three times, served as Chief Justice of Jamaica twice, and served as the President of the Legislative Council of Jamaica, Chancellor, & Commander-In-Chief of the colony of Jamaica and the territories theron depending in America during and following the period of the First Maroon War.
In addition, "Jamaica in Slavery & Freedom" published by The University of the West Indies Press, refers to Gregory as a Lieutenant Governor, citing his own statement that in 1737, a quarter of the population of Jamaica was wiped out due to an epidemic that struck Kingston. Given that this title was often used historically to denote the "de facto second-in-command", it is fitting for him to have held it. A deep examination of Jamaica's colonial history indicates that Gregory's accumulation of such a diverse array of top-tier positions in the colony is without precedent in Jamaica's history.
He held the highest judicial, administrative, executive, military, and political positions in Jamaica, at least three of which, President of the Legislative Council, Commander-in-Chief, and Chancellor, he is known to have held simultaneously during turbulent times. With this in mind, we are forced to confront that at this point he was the highest legislative authority, overseeing the creation and passage of colonial laws, the apex of judicial authority, presiding over the colony's legal system and enforcing the law, and held the most senior military position, commanding the armed forces of the Colony and its associated American territories. It is fair to say that tens of thousands, if not more, enslaved lives were directly impacted as a result.
These attributes, combined with his brother's prominence and wealth as a planter and his father's political roles and involvement with Peter Beckford Jr and other powerful colonial figures, paint a picture of a family that wielded an implacable grip on the levers of colonial authority and plantocracy. It is also of note that Gregory being the most executive military officer on the Island during conflict was not contingent on his gubernatorial office, as was the case with many of his contemporaries. With this in mind, it would be fair to assert that, uniquely, this individual symbolised the entire weight of the colonial system. It is certainly a curious oversight of history that while Edward Trelawny is widely celebrated for envisioning and executing the peace treaties with the Maroons, Gregory's tenure involved advocating for the treaties in the midst of active conflict, years before Trelawny's ascent to office, a far riskier and more uncertain environment. His prescient contributions are almost entirely unsung in historical narratives, which diminishes the complexity of The First Maroon War's resolution.
Writing in 1790, Captain Philip Thicknesse echoed the remarks made by The Honourable John Gregory in 1737 to his English audience, "For my part I know but two ways of dealing with an enemy, either by force or treaty; the first we have often tried." The famous treaties of 1739 and 1740, established after Gregory's governorship, are described as a turning point in ending guerrilla warfare and integrating the Maroons as "useful neighbors." It cannot be ignored that Gregory's prescient recommendations laid the groundwork for these peace agreements.

## Early life

John Gregory came into the world in 1668 in Spanish Town, Saint Catherine Parish, Colony of Jamaica, the offspring of Matthew Gregory and his wife Jane Archer.

## Career

As a window into Gregory's character, Charles Leslie, a Barbadian writer who authored A New and Exact History of Jamaica, describes him in 1740 as a man "who always acted with that firmness and prudence which became one in such an eminent station; his character is to be strictly honest, and severely just; no motives could ever persuade him to forgive the crimes of convicts, nor could the solicitations or prayers of the most considerable, induce him to deviate from the known laws and rules of justice."
In 1733–35, Gregory was appointed Chief Justice of Jamaica. As a long-time and respected member of the Legislative Council of Jamaica since 1717, John Gregory rose to the position of President from 1735 to 1751, illustrating his enduring commitment to governance. 1736, John Gregory, President of the Council in Jamaica, was searching for a way to bring the protracted Maroon War to an end. He reported that he had tried:
“to propose a treaty to such as have been out for the space of five years promising them liberty and lands to cultivate if they would submit on condition that they would clear the woods of such as resolve to stand out, and entertain no more amongst them.” However, Gregory encountered a significant practical obstacle: “He had been unable to procure any that would venture to carry the message to them though upon promise of reward.” In light of this failure, Gregory advanced an even more unconventional plan. He suggested that the home government could assist by purchasing the freedom of 200 enslaved individuals: “such as we should judge could be best depended upon, and put them under a British establishment as to their pay,” with their principal task being to track down and subdue the Maroons.
The Council of Trade and Plantations in London did not endorse Gregory's proposal. While they conceded that “negroes inured to the heat of the climate may be better able to bear the fatigues attending any expedition through the woods,” they voiced strong reservations about the wisdom of creating such a force. They reasoned that if this proposed “black regiment” were inclined to sympathise with people of their own color, it could become “a party of much more dangerous consequence than those of the mountains.” Recent events had shown “how little confidence may be placed in any negroes,” and the late rebellion in Antigua had vividly demonstrated the risks of arming Black individuals. Thus, the very qualities that made these men suitable for the work—adaptation to the climate and terrain—also raised fears that granting them arms and relative autonomy would backfire, compounding, rather than resolving, the colony's security challenges.
In 1737, Gregory, President of the Jamaican council, urged legislation against the "evil" of hiring out enslaved labourers, fearing it allowed them to gain autonomy, disrupt white dominance, and incite rebellion. Sir Nicholas Lawes had similarly argued earlier that it was a "great evil that owners of slaves permitted them to ramble throughout the island," as it gave them "opportunity of plotting insurrections" and "encouraged thieving." Gregory's concerns echoed these fears, particularly after the 1736 Antigua conspiracy, where enslaved workers in skilled trades were blamed for unrest. Despite his efforts, the Jamaican assembly rejected his proposal, prioritising economic profit over colonial stability. This is one demonstration of an individual focused on maintaining strict, unyielding dominance over an oppressed population. This stance underscores his role not just as a magistrate or administrator, but as an enforcer of a harsh social order, capable of imagining and advocating policies that increased surveillance and control.
This same year, John Gregory, writing from Jamaica, reported to the Board of Trade about the dire mortality rates among the colony's white inhabitants. He wrote, “I am sorry to acquaint Your Lordships there has been an Exceeding great Mortality among the Inhabitants. I have been Credibly informed there has been buried in the Town of Kingston within these four Months five Hundred White people; some indeed of them Sailors but the greatest part dwellers on Shoar tho the whole Number of Inhabitants of that place are not Computed above Two thousand.” Perhaps the most potent single thing in undermining the ability of white people to resist the inroads of tropical disease was the universal and excessive drinking of rum. 'Rum Punch is not improperly called Kill Devil,' said Leslie, 'for Thousands lose their lives by its Means.'
Notably, Gregory assumed the role of Acting Governor of Jamaica on three occasions. In 1735, he temporarily held the position following the death of John Ayscough. Subsequently, in 1736–1738, he assumed responsibilities after the passing of Henry Cunningham. In 1737, the Stamford Mercury published a letter addressed to John Gregory from the merchants of Kingston, referring to him as ”The Honourable John Gregory, President of the Council and Commander-in-Chief in and over his Majesty's island of Jamaica.” In 1738 he was again appointed Chief Justice of Jamaica. His last stint as Governor occurred in 1748 when Edward Trelawney embarked on an expedition to St. Domingue and Cuba from February 14 to April 1. In a letter from John Gregory to Thomas Pownall, dated 17 July 1759, he expressed a desire to acquaint the board that he had no intention of returning to the island of Jamaica and recommended a gentleman by the name of 'William Lewis' to be of the Council in his stead. Gregory spent his later years residing in his residence on Conduit Street, St George Hanover Square, London, until his passing in 1764.

## Ancestry

The Gregory family hailed from the hamlet of Hordley in Wootton, West Oxfordshire, where they had called 'Hordley House' home since the mid-15th century. John's brother, Dr. Matthew Gregory, a physician, politician, prominent slaveowner, inherited the estate in St. Thomas, Jamaica named "Hordley" in homage to their ancestral home. His brother's deep entrenchment in the institution of slavery, as one of the colony's most prominent planters, is evident in his being mentioned 35 times in the letters of the infamous Simon Taylor. Taylor's letters frequently display a sense of dominance, disdain, self-assuredness, and condescension with equals or superiors, which one might expect of the ruthless, morally void, machiavellian figures of history. And yet his references to John's brother, Dr Mathew Gregory, often reflect a tone of deference for his relentlessness and effectiveness. In his private letters, he remarked that Dr. Gregory ‘had made himself a perfect master’ in one particular dispute over resources in 1774, for example. Taylor also advised Chaloner Arcedeckne that Gregory's name must not be mentioned in legal documents, aligning with Mathews's reputation of being a Chief Promoter of various suits that would have a noticeable implications for surrounding plantations. His deep fondness for law and his ability to leverage his connections to dominate clearly made him a highly formidable figure. Hordley was inherited many years later by Matthew Gregory Lewis, the great-grandson of John's aforementioned brother, who vividly recounted his experiences as the estate owner in his book titled "Journal of a West India Proprietor.” Governor Gregory's nephew was a 1st cousin 2x removed of the infamous Sir Henry Morgan, and his daughter, Mary Elizabeth Byndloss, married Thomas Beckford Esq, grandson of the notorious Colonel Peter Beckford. And their daughter, grand-niece of Gregory, Mary Ballard Beckford, was wife of the vehemently pro-slavery judge, Chief Justice, and historian Edward Long. John's grandfather, Thomas Gregory, great-grandfather, Francis Gregory, and great-great-grandfather John Gregory, were all members of the prestigious Gray's Inn. Whilst born into a family of the landed gentry class who had a mansion house in Oxfordshire, he wasn't of immediate aristocratic stock as was the case with many of his contemporaries. It is worth noting, though, that Gregory's great-grandfather, Francis Gregory, was himself a great-grandson of The Right Honourable John Mordaunt, 1st Baron Mordaunt, common ancestor of the Earls of Peterborough, and his wife Elizabeth de Vere, of the famous House of de Vere. Francis's wife and John's great-grandmother, Elisabeth Bennet, was the daughter of Sir John Bennet, ancestor of the Earls of Tankerville, and his wife Lady Anne Weekes. Other notable figures in his family include his granduncles, Francis Gregory D.D, who was Chaplain to King Charles II, and Henry Gregory, Rector of Middleton Stoney Henry was the father of Elizabeth Gregory, the wife of Sir John Pratt and mother of Lady Grace Pratt, wife of John Fortescue Aland, 1st Baron Fortescue of Credan. And also his great-granduncle, Sir John Bennet of Dawley, Harlington, Middlesex, a son of Sir John Bennet aforementioned, whose two sons were John Bennet, 1st Baron Ossulston, also a student of Grays Inn, as seemed to be a tradition within the Gregory Family and their descendants, and Henry Bennet, 1st Earl of Arlington. His grand-aunt, Elizabeth Bennet, married The Right Honourable Sir Robert Carr, 3rd Baronet. And John Gregory's great-great-granduncle Sir Thomas Bennett was Lord Mayor of London. It isn't known whether John Gregory's grandfather was in contact with this family of his, but if so, then it's plausible to assume that his aristocratic cousins and other more distant family members certainly contributed to the family's prominence and social standing at the time.