avid Baird had been imprisoned for four years at Seringapatam after the defeat of Baillie's contingent at Pollilur in 1780. Sir Walter Scott records that Baird's mother, on hearing of her son's fate, remarked 'I pity the lad that's chained to Oor Davie.' The inclusion, prominently beneath Baird's feet, of a barred window, alludes to Baird's imprisonment, although Wilkie has used artistic licence to enable him to show the prison and the Watergate together. In fact, the two sites are about 100 yards apart, on the North side of the island of Seringapatam.

Wilkie made numerous pen and watercolour preparatory sketches and studies for his painting, exploring different positions for the key figures. An oil study for the head of Baird is in the Scottish National Portrait Gallery, Edinburgh (PG 644) and the energetic pen and ink sketches in the Scottish National Gallery (D.4977; D.4981) show Wilkie exploring various positions for the grating, the step or steps above it, and Baird's related stance.