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The present work, which until recently was in the collection of the sitter’s descendants, shows Sir John Taylor, a Jamaican landowner and avid patron of the arts.

Sir John Taylor was the second son of Patrick Talizour and Martha Taylor, daughter of George Taylor of Caymanas, Jamaica. Patrick was a merchant who established a profitable business in Kingston, Jamaica, later assuming his wife’s name on marriage. After Patrick’s death the majority of the estate, which included a sugar plantation, passed to Taylor’s elder brother Simon, with whom Taylor and his family are depicted in Daniel Gardner’s ambitious pastel portrait [Christies, 13 June 2001, lot.4].

Although Taylor’s early education is not known, we know through family papers that in March 1761 he matriculated at St John’s College, Oxford, and on 28th June 1764 he graduated with an M.A. In 1770 Taylor embarked on a Grand Tour – a then social custom for all middle-class young men, where he encountered and bought numerous paintings via Gavin Hamilton, including a landscape by Richard Wilson in 1773. Interestingly, Taylor also posed as a model for Johan Zoffany’s masterpiece The Tribuna of the Uffizi, for which he must have modelled when in Florence c.1773 – he can be seen in the group on the left.

In 1774 Taylor wished to marry Elizabeth Haughton, daughter of Philip Haughton and Mary Brissett of Jamaica, and step-daughter of Jamaican landowner Neil Malcolm, although marriage plans dissolved on account of Taylor’s supposedly wild and extravagant lifestyle. On the 17th December 1778, four months after Taylor was created a Bt. and the same year the present work was painted, the pair finally married and they had two sons and four daughters.

Taylor died in 1786 whilst in Jamaica tending to his wife’s plantations which suffered badly following a number of hurricanes, and, following his death, Elizabeth returned to England where she died in 1821.

The present work is quite unusual insofar that Smart rarely signed and dated his works on paper. It is highly possible that this work was intended as a preliminary version and sent to Taylor for his approval before worked up onto ivory by Smart. We know that Smart produced a finished work [whereabouts unknown] as an engraving of it was made by the London engraver William Dickinson, who also engraved Reynolds’ portrait of Taylor’s wife Elizabeth in 1783.