The famous Jacobite heroine Flora Macdonald lived on South Uist, in the Outer Hebrides. In 1746, on the neighbouring island of Benbecula she met Prince Charles Edward Stuart, the Young Pretender, in flight after the disastrous defeat at Culloden. She helped the Prince escape by boat to Skye, disguising him as her maidservant. She was arrested for her part in assisting him and taken prisoner to London. After her release in 1747 she commissioned this portrait which she gave to the captain of the ship which had brought her south, in thanks for the kindness he had shown her.