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Simon Taylor was born in Jamaica in 1740, eldest son of Patrick Tailzour, who had assumed the name Taylor on his marriage to Martha Taylor. Patrick had come out to Jamaica from Borrowfield, Scotland and established himself as a merchant in Kingston. Simon Taylor began his career as an attorney for absentee planters, became a sugar planter in his own right and at his death in 1813 he was reputedly the richest man in Jamaica. He was active in Jamaican politics and society, being member for Kingston in the Jamaican Assembly, 1763-81, and for St. Thomas in the East, 1784-1810; Custos; Chief Justice of the Court of Common Pleas; and Lieutenant Governor of Militia. He never married, although he had a large illegitimate family. For an account of his life and business, see R.B. Sheridan, "Simon Taylor, Sugar Tycoon of Jamaica, 1740-1813" in Agricultural History Vol.45, No.4 (Oct. 1971) pp. 285-296 (a copy is available at ICS) General Nugent, Governor of Jamaica, 1801-1806, described Taylor in 1806 as "...by much the richest proprietor in the island, and in the habit of accumulating money, so as to make his nephew and heir one of the most wealthy subjects of His Majesty. In strong opposition to Government at present and violent in his language against the King's Ministers, for their conduct towards Jamaica. He has great influence in the Assembly, but is nearly superannuated. He has most extraordinary manners and lives principally with overseers of estates and masters of merchant vessels; but he has had an excellent education [he went to Eton], is well informed and is a warm friend to those he takes by the hand. He is also very hospitable and civilised occasionally, but is said to be most inveterate in his dislikes." [P. Wright, ed. Lady Nugent's Journal (4ed., Institute of Jamaica 1966) p318] Simon's heir was his nephew, Sir Simon Richard Brissett Taylor (1785-1815), and after the latter's death his eldest niece, Anna Susannah Watson Taylor (1781-1853), inherited the estates. She had married George Watson in 1810 and the additional name Taylor was assumed at the time of the inheritance.