Cunningham cultivated the interest which his father had gained in Stirling Burghs and built up one at Inverkeithing, buying tenements from the 1st Earl of Rosebery, whom he succeeded as provost in 1720. ‘A man of pleasant manners and great address’, he was
reputed the best boroughmonger in his time. There was no doubt sound policy, as well as an appearance of goodness of heart, in the attention that he showed to his constituents. He did not, like many of his brethren, make an evident distinction between the first and last year of a Parliament, but was uniformly courteous and kind. And hence, though a professed ministerialist, he was esteemed by a set of neighbours that were either hostile to the family of Hanover or in opposition to Sir Robert Walpole.2Extracts Stirling Burgh Recs. 1667-1752, pp. 55, 130, 143; W. Stephen, Hist. Inverkeithing and Rosyth, 30-31; Ramsay of Ochtertyre, Scotland and Scotsmen in 18th Cent. ii. 120-1.
Under George I he sat for Stirling Burghs, from which he transferred to the county in 1727, voting with the Administration in every recorded division, except that on Lord Cadogan in June 1717, when, with most supporters of Argyll, he voted with the Whig minority, dining with the Duke a few days later. In 1715 he became muster master in Scotland, which he gave up the following year to become a commissioner for the forfeited estates, described as ‘the honestest fellow among them’, resuming it when the work of the commissioners ended. In 1733 he was wounded while acting as bodyguard to Walpole against an anti-excise mob. At the end of that year he asked Walpole for a post freeing him ‘from the trouble of parliaments and elections’. He was appointed governor of Jamaica in the new year, but his departure was delayed by his being sent to Stirling at the request of Ilay, Walpole’s electoral manager in Scotland, to oppose James Erskine, a former agent of Ilay’s, and Thomas, Lord Erskine, who were standing as opposition candidates.3More Culloden Pprs. ii. 175; HMC Laing, ii. 185-6; Hervey, Mems. 165; Spalding Club Misc. iii. 54-55. He did not arrive in Jamaica until 18 Dec. 1735, dying less than two months later, 12 Feb. 1736, aged 59. His estates were subsequently sold to pay his debts.4F. Cundall, Govs. of Jamaica in the first half of the 18th Cent., 166-70; Ramsay, 121.