The 775-ton 36-gun East Indiaman Pitt, built at Gravesend on the Thames in 1780 for the London entrepreneur George Mackenzie Macauley, made four voyages to the East between 1785 and 1793.
Alderman Macauley (1750-1803) was a partner with John Turnbull and Thomas Gregory in a firm which specialised in government contracts including the supply of victuals to British troops in Canada, the import of tea from China and the insurance of ships at Lloyd's. Macauley's whiggish sympathies during the French Revolutionary War prevented him becoming Lord Mayor of London. However, he was clearly well-connected and enjoyed 'insider' information because within a few days of the British government's secret decision in August 1786 to begin transporting convicts to New South Wales, Macauley's firm offered their ships. The offer was refused and the matter put out to tender, but Macauley's ships have been called the 'Phantom First Fleet'. In the actual First Fleet (1787-1788), The Lady Penrhyn, who carried an all-female passenger list of 101 women convicts, was under contract from the firm of Turnbull, Macauley and Gregory.
Under the command of Edward Manning, Pitt sailed from Yarmouth on 17th July 1791 with 352 male and 58 female convicts and arrived at Port Jackson, New South Wales on 14th February 1792, a voyage of 212 days. Twenty male and nine female convicts died during the voyage, and five male convicts escaped during a stop at the Cape of Good Hope. In August 1793, at the time of this painting, she was under the command of John Garrard, who sailed her from Portsmouth to India in August, returning the following year. In 1795 she was purchased by the Royal Navy and saw service as H.M.S. Doris until she was wrecked, and burned to prevent capture, off Quiberon during the campaign which led to the battle of Trafalgar in 1805.
Thomas Whitcombe was one of the leading painters of the French Revolutionary Wars. He spent the majority of his working life in London and painted over one hundred and fifty actions of the British fleet, together with fifty plates for J. Jenkins' publication, Naval Achievements of Great Britain. He exhibited a total of fifty-six marine paintings at the Royal Academy between 1783 and 1824, and also exhibited at the British Institute in 1820.