Prince Charles, the eldest son and heir to James Francis Edward Stuart (1688 – 1766), ‘The Pretender’ to the British throne, is depicted here in his mid-twenties. Portraits of the prince following the 1745 uprising – such as this example - often highlight both his military role and Scottish heritage. While his family's Stuart blood was his claim to the throne, the Jacobite cause throughout this period had been rooted in Scotland, and it was here that the most significant support during both the '15 and '45 Jacobite uprisings had been built. As such, these Scottish-focused portraits were a key part of Jacobite propaganda and have since reflected a fleeting moment when the prince seemed poised to fulfil his royal destiny.

Those loyal, and vocal, followers of James III (as he was known by those who recognised him as king), and latterly of our sitter, who was popularly, and affectionately, known as ‘Bonnie Prince Charlie’, were supporting an ancient dynasty, destined to rule Great Britain once more and dethrone their foreign, protestant cousins from the monarchy. With the birth of Prince Charles, and later his brother Henry, the Jacobites had renewed hope for another – and, ideally final - rebellion. As this portrait shows, Prince Charles was sprightly and youthful, nurtured with regal destiny in mind. Meanwhile in Britain, it was no secret that (the very German) George I and his only son, George Augustus, despised each other, which mirrored, somewhat, the monarchical uncertainty that had previously presented Charles’s father, James, his first opportunity at gaining the British throne when William and Mary, and later Queen Anne, bore no children of their own, thus providing a genuine prospect of him inheriting the crown by virtue of his direct Stuart ancestry.

Despite the aspirations of Bonnie Prince Charlie he was never to be known as Charles III in Britain. His own attempt at reclaiming the British throne, known as the ’45, proved more successful than his father’s previous attempts, having regained Scotland and making it as far as Derby, but he retreated due to a lack of English and French support. The Jacobite uprisings, and the potential reclamation of the British throne by the Catholic branch of the Stuart dynasty, still tempts historians today with ‘what if?’ scenarios that could have drastically altered the course of British history.

The artist associated with the Harlequin portraits, James Worsdale (1692 - 1767), was a servant of Sir Godfrey Kneller, who became a studio assistant and copyist. He was eventually thrown out by Kneller for marrying a niece of Lady Kneller, and for stating that the painter was his father. Considering the present work, in terms of the composition and handling of paint, there are distinct similarities in quality with other works by Worsdale in public collections. He was known for his speculative compositions, and it is not unlikely that he would produce a composite portrait of the prince as a commercial venture for the Jacobite market. Despite its possible commercial origins, the image has become a lasting romantic symbol of the Stuart cause.