Taylor’s letters reflect the dilemmas of slaveholding colonial planters with British identities who had, nevertheless, become disillusioned about their place within the empire. By 1806, Taylor was recommending his nephew, and principal heir, Sir Simon Brissett Taylor, who was by then aged twenty-two, to explore the possibility of moving the Taylor family and their investments to the United States. He later went cold on the idea, but the sentiment behind it perhaps showed the depth of his disillusion with Britain and reflected his fears about the potential impact of an end to the slave trade. Indeed, he used financial concerns to try to dissuade his nephew from taking up a seat in Parliament.
[…] Whoever has impressed these notions of going into Parliament into your head does not know how you was circumstanced nor knows the situation of the colonies. I who know both perfectly advised you to go to North Americato see that country, and to look out for a spott where you conceive you may as well as your mother and sisters be quiet and safe. As for any predilection for that country I can have none I never was there nor do I know any one in it I do know it is a very fruitfull country and that a man there with common industry can maintain himself and a family nothing tho could have made me advise you to go and settle there but dire necessity. […]
(Taylor Family Papers, I/G/27, Simon Taylor to Simon Richard Brissett Taylor, Kingston, 30 August 1806)