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This portrait marks not only Stirling's patronage of Sir Henry Raeburn - in which it fits into a series of portraits of Edinburgh worthies, such as those of Dr William Robertson (University of Edinburgh) and The Rev. Hugh Blair (Kirk of the Canongate, Edinburgh), which Raeburn painted in the last decade of the eighteenth century and which share aspects of composition and indeed of studio furniture.

The portrait is, therefore, an appropriate record, perhaps, of Stirling's first appointment as Lord Provost of Edinburgh, the Mayor of the city, in 1790, an office for which he was again chosen in 1794 and 1798. The three chains that are just visible across the waistcoat of Stirling's black velvet suit are - with a gown that the sitter is not wearing - the distinctive dress of the Lord Provost. Stirling had achieved this influential office on his return to Scotland from the West Indies, where he had made his fortune, first as Secretary to Archibald Stirling of Keir, a great planter, and then as Secretary of Sir Charles Dalling, Governor of Jamaica. On his return, Stirling entered the banking house of Mansfield, Ramsay, & Co., and this, and his marriage to Alison, the daughter of James Mansfield, the senior partner, set him firmly on the cursus honorum of Edinburgh civic dignity. Above the call of normal duty his firm but prudent treatment of the Reform rioters in 1792 was rewarded by a baronetcy in July of that year. Stirling died February 17th, 1805, leaving three sons and a daughter. His eldest son Gilbert succeeded him in the baronetcy, which became extinct on his death in 1843.

Although either of these achievements might occasion the commission of a portrait from Raeburn, a very specific instance is alluded to both by the document that the Lord Provost holds and by the building shown with some attention to detail in the background. The Edinburgh Bridewell, named on the scroll, was the new prison for the city built during Stirling's period of office from 1791 to 1795. Although this may seem a somewhat grisly object for such commemoration it is important to remember that this was a part of Robert Adam's total plan for the redevelopment and the beautification of Edinburgh, as a perfect functioning city along enlightenment principles.

From 1751 when there was a serious tenement collapse, patrons and architects had been considering the question of how to build a New Town to the old town of to remedy the narrow streets and perilous construction of the older buildings. As early as 1753 an Act For Erecting several Public Buildings in the City of Edinburgh; and to impower the Trustees therein to be mentioned to purchase Lands for that Purpose and also for Widening and Enlarging the Streets of the said City, and certain Avenues leading thereto. Was passed under the tutelage of men such as Sir Gilbert Eliot of Minto, who recognised not only the necessity of new building, but the possibilities that existed for a city that could be laid out according to rational principles. This was an opportunity grasped by few towns in the British Isles and realised by none of them on the scale of the New Town in Edinburgh.

Necessarily, the New Town was to be provided with public buildings, both to fulfil its purpose lest it become simply an affluent residential suburb, and to provide strong focal points. The General Register Office, the first purpose-built record depository in Britain, was built to the designs of Robert Adam between 1773 and 1774, and it is with the name of Adam and his brothers that the New Town is associated, although individual commissions were also given to other prominent architects, such as Adam's rival Sir William Chambers, which further enhanced the prestige of the project, however much it may have bruised feelings. It is much to Sir James Stirling's credit that one of the first acts of his incumbency as Lord Provost was to commission Robert Adam to produce designs in 1790 for the houses in Charlotte Square, planned since at least 1767 to be one of the main focuses of the New Town. Adam's design for treating each side of the square as a single architectural unit, a single ''palace front'', was an ingenious means of avoiding the numbing repetitiveness of individual, single terraced houses when viewed en masse, and although the square was not completed until 1820 it was to be profoundly influential in Europe well before that date.

Perhaps unusually, it is not Charlotte Square that Stirling wishes to be remembered for, however, by the building of the Edinburgh Bridewell. Although a new prison had not been considered among the measures for the ordering of the New Town, by 1790 it was recognised that one was necessary. Adam won the competition in 1791 for what was to be his last public building. This was completed by 1795 to his designs as shown in the background of Stirling's portrait. It is a design unrecognisable on first inspection as Adam's work, since it employs the stepped gables of traditional Scottish architecture and a strong fortress shape as a reminder of its function. There is a sense that, even in the midst of the Enlightenment made stone, prison must be made to be a severe and dreary business.

Raeburn's portraits of prominent men of Edinburgh of the late 1790s and early 1800s were not conceived as a series, although it is possible to view them as just such a record now. They share broad similarities in composition, for example the seated pose in which the subject is placed firmly to the front of the picture plane, invariably commanding the viewer's attention by a combination of a direct gaze and an emphatically stretched arm. They exhibit the same palette, restricted to black and white for the sitter's dress, offset by a rich red damask chair and a darker red drapery to define the picture space. A further element common to these portraits is that they are explicitly records of achievement: Dr William Robertson is shown with his mace of office as Principal of the College of Edinburgh on the table behind him, and a the books on which it rests allude - explicitly through their visible titles - to his long career as a historian. Similarly here, not only does Stirling’s dress proclaim his office, but the scroll he holds names the Edinburgh Bridewell and the building itself, almost as a painter's sleight of hand is revealed in the background so conveniently and at such a scale that it might be sitting on the table behind him.