The 1780s were a transformative decade in Taylor’s life. The American War and its aftermath transformed his political outlook towards a distrust of the British government in London, a perspective that became more entrenched with the advent of the parliamentary campaign against the slave trade in 1788. His sugar estates were adversely affected by the several hurricanes that hit Jamaica in the first half of the 1780s, and a fire devastated the works of his estate at Lyssons in 1784. His elder brother, Sir John Taylor, died on a visit to Jamaica from England in May 1786. Thereafter, Taylor assumed the role of head of the Taylor family, managing the plantation that belonged to his late brother’s wife, Lady Elizabeth Taylor, in western Jamaican, and making his brother’s son, Sir Simon Richard Brissett Taylor, his principal heir.
[…] I have had the misfortune to have lost my poor brother, who was taken ill at his estate down to leeward, and I believe by some mismanagement of his doctors thrown into a dropsy, on which I advised him to come up in a man of warr that was at Lucea to this town which he did but was so far gone that his life could not be saved, and he died on the 6th of last month. His death has been a very severe stroke on me, as well as his little family, which I must now take all the care of that I can, indeed they are so very young just now, that they will be for some years but with their mother, and I must endeavour to settle my matters so as to go home three or 4 years hence, when I have gott rid of the effects of the fire, the hurricane, and dry weather and other calamities that have pursued me for these three years past, and can make an arrangement of my brothers affairs, which will give me a great deal of trouble and fatigue. His wifes estate lying 150 miles from this town, I have been obliged to go there since his death, I must go there again the middle of this month, and must visitt them twice a year for there is really no person in that part of the country that there is the least dependance to be putt in, and that added to my other business will give me enough to do God knows. […]
(Vanneck-Arc/3A/1786/9, Simon Taylor to Chaloner Arcedeckne, Kingston, 1 June 1786)