The present picture is dateable to circa 1790, during the artist's period in Dublin from 1787-1793. Robert Cunninghame (d.1810) was the son of Colonel David Cunninghame of Seabegs, Fort Major of Stirling Castle. He entered the army, whilst still young, as an ensign in the 20th Regiment of Foot in 1746 and served as a volunteer at the Battle of Culloden in the same year. By 1751 he had been appointed A.D.C. to George Stone, Archbishop of Armagh, when the latter was serving as a Lord Justice. The greater part of his professional life, both military and political, was spent serving in Ireland. He sat in the Irish Parliament as M.P. for Tulske (1751-1760), Armagh (1761-1768) and Monaghan (1769-1796); at Westminster he sat as M.P. for East Grinstead (1788-1789). In 1754 he married Elizabeth, daughter and co-heiress of Colonel John Murray, M.P. for Monaghan, and Mary, widow of Lord Blayney, and daughter and heiress of Sir Alexander Cairnes 1st Bt., of Monaghan. The marriage was childless though it did bring Cunninghame considerable estates in Co. Monaghan. In 1793 Cunninghame was appointed General in charge of the Fifth Royal Irish Dragoons (Lancers), though six years later they were disbanded for insubordination. Cunninghame, by now ennobled as Lord Rossmore of Monaghan, was exonerated and excused any responsibility for his regiment's behaviour. Rossmore was succeeded by his nephew Warner William Westenra of Rathleague, son of William Westenra and Harriet Cairnes, his wife's sister. Westenra inherited the family's principal seat and estate Rossmore Park, Co. Monaghan, but Mount Kennedy, which Rossmore had purchased in 1769, was inherited by his niece.