James Stirling, son of a fishmonger from Marlin's Wynd, was a self-made man who went to the West Indies as a clerk to plantation owner Mr. Stirling of Keir. Through exemplary conduct, he became Secretary to the Governor of Jamaica, Sir Charles Dalling, accumulating considerable wealth before returning to Edinburgh. He became a partner in the banking firm "Mansfield, Ramsay, & Co." and further advanced his fortune by marrying Miss Mansfield, the principal partner's daughter. Entering Edinburgh's Town Council in 1771, he served as Treasurer in 1773-74 and frequently as a magistrate before being elected Lord Provost in 1790. His tenure coincided with the turbulent political climate of 1792, when agitation for Royal Burgh reform and opposition to the Pitt administration's restrictions on the press had inflamed public sentiment. Henry Dundas (Lord Melville) had become particularly unpopular for opposing reform, being burned in effigy across Scotland. As the King's birthday approached on June 4th, Edinburgh authorities faced the challenge with considerable uneasiness, though their precautionary measures proved imprudent and only served to further antagonize the populace.