Both Frederick, Duke of York, and his elder brother George, Prince of Wales (later George IV), were close friends of the Marquess of Hastings (1754-1826). A contemporary report suggests that Hastings commissioned this portrait as a gift for the Duke of York, who gave Hastings his portrait in return. George IV, who had already exchanged portraits with Hastings as a mark of friendship, purchased this painting at the posthumous sale of the Duke of York's collection in 1827.

Hastings's appointments as Governor-General of Bengal in 1813 and Governor of Malta in 1824 were the culmination of a successful military career. He is depicted wearing the undress uniform of a colonel while ADC to George III, an appointment he held from 1782 until 1793.

This is one of the last portraits that Reynolds painted with a sitter posed in front of him. Six sittings are recorded in the artist's sitter-book in June and July 1789. On 13 July, the day after the last sitting, Reynolds recorded that his eye 'began to be obscured'. However, a newspaper critic wrote on 28 September that the portrait would be 'safely as well as easily finished'. Reynolds's difficulties in seeing are not apparent in this heroic image in which the sitter's pose and stance suggest intelligence and confidence in the face of danger. The portrait is one of Reynolds's most impressive achievements in a career which saw him appointed the first President of the Royal Academy in 1768 and during which he painted many portraits of the leading figures of British society. His keen intellect is reflected in the Discourses on Art addressed to the students of the Royal Academy between 1769 and 1790. However, Reynolds was not able to please George III and Queen Charlotte who disliked him, even though he was appointed Principal Painter to the King in 1784.