Cunningham, Waddell (1728/9–1797), merchant and public figure in Belfast, was born at Ballymacilhoyle in the parish of Killead, Co. Antrim, the youngest son in the large family of John Cunningham and his wife, Jane, daughter of James Waddell of Islandderry, a townland in the parish of Dromore, Co. Down. The extended families of Cunningham and Waddell had interests in farming, linen, provisioning, and overseas trade. By 1752, no doubt with support from his family, Waddell Cunningham was in New York trading near the meal market; just as the Seven Years War was beginning (May 1757), he became the local partner of a Belfast merchant, Thomas Greg (1718–96). While carrying on a wide range of commercial activities, the firm of Greg & Cunningham specialised in the flaxseed trade with Ireland and became ‘the most successful Irish-American transatlantic trading partnership of the colonial period’ (Truxes (ed.), 1). Cunningham amassed a large fortune from trade (some of it illicit) during the war, and became one of the largest shipowners in the American port. This enabled the partners to purchase a 150 acre estate (which they renamed Belfast) on the West Indian island of Dominica, just as it was passing, by the treaty of Paris (1763), from French to British rule. It is possible that the estate was managed by Greg's brother John (d. 1795).
Some time after suffering imprisonment for assaulting a fellow merchant (July–August 1763), Cunningham returned to Ireland, leaving the firm in the charge of junior partners until its dissolution (1775). In Belfast he entered into a second partnership with Greg (May 1765) comprising all their business activities other than those in New York; he also married (November 1765) Greg's sister-in-law Margaret (d. 1808), second daughter of a Belfast merchant, Samuel Hyde (d. 1744). Cunningham lived in a large house (formerly that of a sovereign, David Butle), in Hercules Street, later renamed Royal Avenue, which served also as the premises for his many business interests, commercial, financial, industrial, and agricultural. Cunningham and Greg started the manufacture of vitriol (for bleaching) at a factory by the Lagan at Lisburn, 12 km from Belfast (1767); they opened up fisheries in Donegal and Sligo, exporting herrings to the West Indies as food for slaves (1770s); they also traded Irish horses and mules for West Indian sugar and American tobacco, the sugar being processed by them at the New Sugar House in Waring Street, Belfast. During the American war (1775–83) Cunningham illegally shipped linen uniforms to the insurgent colonists. He became a middleman on the estate of Arthur Chichester (qv), 5th earl of Donegall, by obtaining leases of land in the Templepatrick district of Co. Antrim, a venture that involved him in disputes with tenant farmers resulting in an attack by ‘Steelboys’ on Belfast and the destruction by fire of his home (23 December 1771).
Despite this setback, Cunningham became the foremost Belfast merchant. As well as those mentioned, he had interests in shipping (with Greg), brewing (John Cranston & Co.), glass manufacture (James Smylie & Co.), and flour milling (with William Harrison). When a chamber of commerce was set up (1783), Cunningham was elected president, a position he held until 1790. In the 1780s (probably in June 1787), in partnership with William Brown (1740?–1794), John Campbell (d. 1804), and Charles Ranken (d. 1802), he opened a bank; known as Cunningham's Bank, it closed (31 December 1793), probably as a result of the recession brought on by the outbreak of war between England and France.
A prominent Volunteer, he joined the movement as a lieutenant in 1778 and was captain of the 1st Belfast company from 1780 until the dissolution of the Volunteers in 1793. Entering politics, he failed to be nominated as a parliamentary candidate for Belfast by its patron, Lord Donegall, at the general election of 1783, but stood for Carrickfergus at a by-election on a platform of parliamentary reform, and was returned – a rare distinction for a presbyterian – by 474 votes to 289 (February 1784). A petition against his return was lodged successfully, but he remained an MP until March 1785, when he was defeated in a new election. It was during this period that Cunningham, probably the wealthiest, most enterprising merchant in Belfast and having, as he did, Caribbean interests, proposed fitting out a ship to engage in the Atlantic slave trade (December 1784). The proposal came to nothing but was the subject of intense debate in the 1920s between two rival Belfast local historians, Francis Joseph Bigger (qv) and Samuel Shannon Millin.
Cunningham played a prominent role on several Belfast boards – those of White Linen Hall, the harbour, poorhouse, and dispensary; he gave money to the first catholic chapel opened in the town (St Mary's, 1784) and to the First Belfast Presbyterian congregation, as well as providing a site for a meeting-house for his own congregation, Second Belfast (1767). Staunch in his advocacy of the reform of parliament, Cunningham became a member of the Northern Whig Club (1790); he was cautious however about catholic relief, for he feared its possible consequences. On 14 July 1792, an organiser of a Volunteer display to mark the third anniversary of the fall of the Bastille, he balked even at a very moderately worded resolution in favour of the catholics. Thereafter he became increasingly ill-disposed towards reform and when the Belfast yeoman infantry was formed (1797) became captain of the 4th company.
Cunningham died 15 December 1797 at his restored house in Hercules Street. He and his wife had no children. His property in Ireland (worth £60,000) passed to James Douglas (1774?–1842), youngest son of his sister Jane, who had married their first cousin, Cunningham's personal clerk Robert Douglas. His name had already passed to Thomas Greg's son, Cunningham Greg (1763?–1830), who took over Greg's business after his death. Waddell Cunningham's portrait was painted by Robert Home (qv). A mausoleum was built over the Cunningham vault at Knockbreda graveyard.