[6][7] 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."

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.

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.

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."

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.

[14][15] 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.

[17] 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.

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.

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.

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.