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In the pastel portraits for which he is best known, Hugh Douglas Hamilton demonstrates an admirable technique, without necessarily pursuing any particular interest in character. It is in his oil paintings, however, that he reveals himself as an observer of remarkable acuity and sensitivity. He is master of the medium, and both from the carefully balanced tones that make up the sitter’s face, and the symphony of blacks that create his costume, we know that we are dealing with an oil painter of the first rank, and the conjunction of the painter’s virtuosity with his sympathetic interest in character produces works of considerable power.

This portrait, unquestionably one of the painter’s finest works, suggests to the full the melancholic and haunted personality of Richard Mansergh St George. The association between Hamilton and Mansergh St George began after the former's return from Italy to Ireland in the early 1790s. Mansergh St George''s wife had died in 1791, leaving her husband a widower with two infant children, and he wished to have a portrait painted of himself as a monument to his grief for her. The -eventual- result of the commission is the full-length portrait by Hamilton now in the National Gallery of Ireland, in which Mansergh St George, dressed in his uniform from the American War, leans in an attitude of grief against a classical tomb inscribed Non Immemor.

It is apparently a conventional exercise of its kind, but the patron’s original desire for the portrait to be painted by Fuselli -the circumstances of the commission being given instead to Hamilton are not known- gives some clue to his sensibilities. The sitter’s correspondence with Fuselli is filled with the Gothic morbidity and preoccupations that had been the stock of literature for two decades. He fantasised about a world in which the dead continued to live and showed a fixation with the past and memory. To this end he decided that the ''dreadful picture (which I shall never see) you are to paint for my children and posterity shall never be seen (nor known) to any person until they arrive at mature years.'' This was to be affected by keeping the portrait -along with one of Mrs St George- in a locked room, together with a chest containing his ''personal histories.'' These would then be revealed to their children at the appropriate time, and the husband and wife, preserved in their strange incarceration, might indeed seem to be resurrected.

This is Mansergh St George at his most extravagantly fanciful. Our portrait is a more immediate and -though never intended to be locked away- private image. In appearance it conforms exactly to the description of him by Lady Eleanor Butler, who saw him as ''one of the most pleasing men I ever conversed with. …very pretty, slight figure, pale genteel Face, his appearance is rendered even more interesting by the black silk cap he wears on his head to conceal the terrible wound he has received in the American war.'' It depicts quite apparently the concerns of a man of sensitive intellect who was disturbed not only by the death of his wife, but also by matters around him. On his return from America Mansergh St George was appalled by the poverty that he found on his estates in Cork and Galway. His response to this was an Account of the State of Affairs in and About Headford, County Galway, which laments the condition of the Irish peasantry, and whilst considering establishing a linen industry to improve matters, doubts the willingness or the ability of his tenants to make the enterprise work. This compassion, and the recognition that it can have no successful outlet, are plainly to be read in this portrait.

The further circumstances of Mansergh St George’s life were to heighten the Gothic resonance of his images, and more pragmatically, to make him an archetype of the troubled condition of the Anglo-Irish landowner at the close of the eighteenth century. In February 1798 he became an early victim of the Irish Rebellion when he was murdered with a rusty scythe by a party of marauders from North Cork and South Tipperary.