A half-length portrait to the right, showing Caldwell in his admiral's undress uniform of the 1795-1812 pattern. The painting is inscribed, signed and dated on the back of the canvas: 'Benjamin Caldwell, Esq., 22 years a captain in His Majesties fleet. R. Horne, 1784'.
Benjamin Caldwell entered the Royal Academy at Portsmouth in 1754 and joined the 50-gun ‘Isis’ in 1756. He then joined Bowcawen’s flagship, the ‘Namur’, in 1759 and saw action at Lagos Bay on 18–19 August and at Quiberon Bay on 20 November that year. He was lieutenant in the ‘Achilles’, 60 guns, in 1760–62 and, after commanding the sloop ‘Martin’ for three years, was made captain of the frigate ‘Milford’. Further commands followed – ‘Rose’ 24 guns, the ‘Emerald’ 32 guns, the ‘Hannibal’ 50 guns – until he was appointed captain of the ‘Agamemnon’ 64 guns in 1781 in the Channel Fleet under Vice-Admiral George Darby. Caldwell then sailed with Rodney and saw action at the Battle of the Saints, 12 April 1782. He remained on the North America and West Indies station until his ship was paid off in May 1783.
In 1787 he briefly commanded the ‘Alcide’, 74 guns, and had a further short command in the ‘Berwick’, 74 guns, in 1790. He became rear-admiral of the white on 1 February 1793 and late that year he hoisted his flag in the 74-gun ‘Cumberland’ under Lord Howe. In April 1794 he was made rear-admiral of the red and moved his flag to the 98-gun ‘Impregnable’, taking part in the Battle of the Glorious First of June. In 4 July 1794 he became vice-admiral of the blue. With his flag in the 74-gun ‘Majestic’ he joined Sir John Jervis in the Leeward Island, becoming commander-in-chief when Jervis return to Britain. He was superseded in command by Sir John Laforey and, slighted, returned home never to accept a further naval appointment. He was advanced to the rank of full admiral by seniority on 14 February 1799.