For many years it was believed to have been painted around 1708; but the discovery of Prussian blue in the coat of Dudley North has led the work to be redated to between 1719 and 1721.

The work has been perceived as having been created to improve Yale's image amid criticism of his unjust enrichment with the East India Company and resultant aristocratic resentment at his wealth.

[1] The larger version was acquired as a gift in 1970 by Andrew Cavendish, 11th Duke of Devonshire, from the collection at Chatsworth House, having come down through family inheritance.

Martin has felt that contemporary viewers perceive the displaying of the portrait by the museum as validating the enslavement of the child depicted saying that "The public says, everything you put up, you believe in, 100%.

[1] The artist Titus Kaphar made an artwork called Twisted Tropes, highlighting the portrait of the black pageboy, but omitting his dog collar, in 2016.

[7] Writing in The Art Newspaper, Nancy Kenney described Kaphar's work as having "collapsed the four white men into a crumpled blur and transformed the boy into a defiant personality, rid of his collar, who stares out at the viewer from a gold frame" and that his work "harnessed indignation over moral travesties past and present as well as glaring deficiencies in representations of people of color today".

The portrait was removed from display in 2021 and replaced with another work by Kaphar called Enough About You for eight months, on loan from the art collectors Arthur Lewis and Hau Nguyen.

[1] In 2019 Kaphar said that in creating his work he had aimed to "imagine a life" for the enslaved child depicted, with his "desires, dreams, family, thoughts, hopes".