Stuart's military career, which took him to Canada, the Caribbean and to southern India, was dogged by failures for which he was twice suspended. Back in Britain in June 1786 he fought a duel with Lord Macartney, governor of Madras, who had been responsible for his dismissal after his alleged mismanagement of the expedition against the town of Cuddalore in 1783. Despite having lost part of his right leg in battle five years previously, Stuart managed to wound his opponent severely. This flattering portrait, which presents Stuart as a conquering hero, his hand firmly on a map marked 'Cuddalore 1783', was begun three months after this incident.