The Portrait Gallery has a wide-ranging collection of art and artefacts relating to the dramatic period of Jacobite uprisings and rebellion in the late seventeenth and early eighteenth centuries. The term Jacobite refers to supporters of the exiled King James VII and II and his heirs. From the revolution of 1688 which deposed the Stuart monarch to the death of his grandson, Prince Charles Edward Stuart, now known as ‘Bonnie Prince Charlie’, the collection includes portraits of the major figures as well as representations of battles and other key moments relating to the Jacobite cause. This portrait of the Jacobite heroine Flora Macdonald (1722–1790) relates to a famous episode that continues to capture the modern imagination: the flight of Prince Charles Edward after his defeat at Culloden in 1746.

In traditional narratives Flora Macdonald is often depicted as a humble peasant girl, but she was actually a cul­tured young woman from an influential family on the Outer Hebrides. In 1746, as Government forces scoured the Hebrides in search of Prince Charles Edward, Flora helped the fugitive leader to reach Skye, disguised as her Irish maid, Betty Burke. It is a beguiling tale of intrigue and deception that has now become part of a romanticised view of Scottish history. By all accounts, the prince was unconvincing as a woman but he managed to evade capture and was picked up from Skye by two French ships to be conveyed safely into exile in France. Flora, however, was arrested and brought to London. She was released under a general amnesty in 1747.

The artist, Richard Wilson, is now best known as a landscape painter but he established his reputation in London as a portraitist. We do not know why or how he came to be commissioned to paint Flora Macdonald, although it is clear that she became something of a celebrity among supporters of the Jacobite cause in the capital. The portrait was probably painted after her release while she was staying in London with Lady Primrose, a prominent Jacobite sympathiser. Flora recalled that Lady Primrose had insisted on her ‘sitting to some of the first artists’. Dr Johnson, who later met Flora in Scotland, described her as ‘a woman of middle stature, soft features, gentle manners and elegant pres­ence’. Wilson’s portrait corresponds with this view: it is a direct and honest render­ing of an unlikely heroine. By tradition, the portrait was presented to a naval officer, Nigel Gresley, who had shown her kind­ness and sympathy during her transfer by ship from Scotland to London; it remained in the Gresley family until it was purchased for the Portrait Gallery in 1931.

This text was originally published in 100 Masterpieces: National Galleries of Scotland, Edinburgh, 2015.