After the defeat of the Jacobite forces at Culloden in 1746 and the prince’s subsequent flight to France, Charles repeatedly tried to rally French support for an invasion on English soil. Despite his father’s pleas, French support never materialised and the Young Pretender was eventually expelled. After years of moving around the continent, in 1774 Charles and his young wife Louisa settled in Florence. By this time he was depressed, abusive and suffering from drink-related ill health. Charles and Louisa separated in 1784, and that same year Charles legitimised his daughter Charlotte by his mistress, and recognised her as his heir. This portrait was painted in Rome during the last years of the sitter's life. At this time Hamilton also portrayed Charles’s daughter in a similar format.