By the 1750s, when Millar was consolidating his portrait practice in Edinburgh, Trotter was already a senior member of the city’s business community. A prosperous grocer and confectioner, he was elected a magistrate in 1744. The following year, presumably after the Jacobite occupation of Edinburgh that autumn, he was appointed by the Secretary of State “provisioner” or victualler to the Duke of Cumberland’s army in Scotland. Trotter is shown with a copy of 'The Caledonian Mercury', founded in 1729 and one of the two main newspapers published from Edinburgh in the 1760s. The specific date on the newspaper (27 May 1767) is evidently some kind of private allusion, perhaps even marking the completion of the portrait a few months before Trotter’s death.