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William Collins Jackson was born in Exeter and in around 1782 joined the East India Company and later went to Madras, where he worked as a clerk (or a ‘writer’), whose job it was to copy accounts and transcribe details of events for the attention of company directors back in England. Although the first few years proved very difficult for Jackson – at one stage he had his pay docked for twelve months – he gradually built-up significant wealth and by the age of twenty-four in 1787, the year the present work was painted, he had been promoted to deputy secretary in the Military and Political Department at Madras. The same year Jackson married Jane Shee, a young widow of considerable wealth whom he had met on board a ship whilst taking leave to England. In around 1789 Jackson was promoted to secretary of military, political and secret matters in Madras and two years later Jane gave birth to a son, William Collins Burke Jackson. In 1796 Jackson was given the post of collector at Ramnad where he built up considerable wealth through his independent trading of cloth, a practice which although was not allowed by the company, was hard to enforce. In 1799, following a high-profile disagreement with a native administrator who accused Jackson of impropriety, Jackson was dismissed and returned to England a very wealthy man, although his reputation would never quite recover.

Jackson, who was by 1787 a young, wealthy, and emerging middle-class gentleman, was typical of the clientele Smart pitched too when in Madras. It is quite possible, given this work was painted in the same year of his marriage, that it was given to his wife as a gift and possibly exchanged with a currently unrecorded portrait of herself.