David Pinkerton was born in the small village of Kirknewton near Edinburgh, Scotland, probably in September 1836, the son of Margaret Hamilton and Benjamin Pinkerton, a corn merchant. He received a parish education and was taught for a time by John Hislop, who was later prominent in education in New Zealand. Pinkerton served his apprenticeship as a bootmaker in Edinburgh, on the eve of that trade's transformation. He married Margaret Fairley on 1 December 1857 at Kirknewton; the couple were to have three daughters.
In October 1860, lured by reports of gold in Otago, he sailed to New Zealand with his wife and members of her family on the Lady Egidia, arriving on 28 January 1861. He had no luck at the diggings and soon decided to settle in Dunedin to practise his trade. He became 'principal knee man to James Mollison, Rattray Street'. According to an old work-mate, Pinkerton helped prepare Mollison's prize-winning entry in the New Zealand Exhibition, 1865. During the 1870s he went into business on his own account, but the growth of bootmaking factories, and the lean years of the 1880s, forced him back into employment as a bootmaker with the firm of A. & T. Inglis.
New sewing machines had undermined traditional bootmaking skills and made factory production profitable. Factories in turn threatened the existence of small businesses. Pinkerton's own experience of these changes drew him into political activity. He belonged to the Ancient Order of Foresters and became involved in the affairs of the Dunedin Operative Bootmakers' Union during the 1880s. He belonged to the Dunedin Freethought Association and was friendly with such men as Robert Stout. He strongly supported Sir George Grey in the elections of 1879 and 1881. By the end of the 1880s, however, he had moved from his inherited liberalism towards a new vision of how to achieve a just society, a vision which stressed the potential role of trade unions and the state. Pinkerton's views owed much to the traditions of artisan radicalism, strong in Edinburgh, which indicted the greed of capital as the main source of sweating, poverty and destitution. The union, in contrast, represented brotherhood and the dignity of labour.
Everybody who knew Pinkerton described him as frank but tactful, and unobtrusive. As one associate said, he was 'always of a give and take nature'. He achieved no prominence in the labour movement until the late 1880s when his conciliatory temperament, allied to firm purpose and considerable skill, saw him pushed into positions of leadership. In 1889 he took an active part in the anti-sweating movement, became president of the bootmakers' union, and helped revive the Otago Trades and Labour Council. During that tumultuous period he worked hard to ensure that the Trades and Labour Council worked closely with John A. Millar and the Maritime Council. In 1889–90 he served on the industrial and workmen's court committee for the New Zealand and South Seas Exhibition. In October 1889 he was chosen as president of the newly formed Tailoresses' Union of New Zealand, and in August 1890 he became president of the Otago Trades and Labour Council. He embodied the characteristics of the 'new labour man' who put loyalty to the movement ahead of all else. He could mix easily with men and women from all walks of life and won their respect because he so readily treated them with respect. Workers accepted his leadership because he was one of them.
Pinkerton was one of those trade union leaders who saw the possibility of winning political influence for the workers. When the Otago Trades and Labour Council and the Maritime Council selected candidates to contest the 1890 general election, Pinkerton was the first chosen. The Trades and Labour Council gave him handsome financial support. He and the other labour candidates – William Earnshaw and John Millar – campaigned together and on election day Pinkerton headed the poll for City of Dunedin. This marked the end of his employment as a bootmaker, but after his departure his work-mates at A. & T. Inglis refused to let anybody else work at his place on the bench.
Pinkerton moved quickly to institutionalise labour's political strength in Dunedin. He helped form the Workers' Political Committee in 1892 and ensured that the Trades and Labour Council, over which he presided until 1893, continued to have a controlling influence on the selection of labour candidates for political office. His tolerant willingness to work with anybody travelling his road triumphed over more sectarian influences and helped to ensure the continuing effectiveness of the Workers' Political Committee.
Pinkerton not only played a major role in the labour movement's successful bid for political influence but also welded the various labour members of Parliament into a 'party'. Pinkerton had a clear idea of what he wanted from the new government and found a powerful ally in William Pember Reeves. It is unclear whether the two men much liked each other, for they came from very different backgrounds, but they made a formidable team. Reeves was articulate and waspish; Pinkerton was genial and conciliatory; both were determined. Pinkerton disliked the posturing and histrionics which dominated parliamentary debates. His occasional speeches were invariably brief and usually impromptu: he spoke to correct error, not to score points. He stayed aloof from the bitter wrangles which occurred so often during his first term. Instead, he worked hard on the Labour Bills Committee, strongly supported advanced Liberal measures, did all in his power to promote Dunedin and Otago, and helped hold the prickly members of the 'labour party' together.
Pinkerton's pragmatism, shrewdness and unfailing courtesy helped to ensure that the fledgeling 'labour party' obtained an extraordinary series of legislative victories. Even during the first term, when the Legislative Council took the sword to most Liberal bills, several acts were passed including the Factories Act 1891, and the Shops and Shop-assistants Act 1892, which regulated conditions in shops and offices. He also worked hard to push through the Truck Act 1891, and the Workmen's Wages Act 1893, which protected workers' wages. He supported an industrial conciliation and arbitration measure, and a proposal to make eight hours the standard working day.
In 1893 the members of the Labour Bills Committee elected Pinkerton chairman. He promptly resigned as president of the Otago Trades and Labour Council, but his influence on it remained strong; in the 1893 election labour candidates, led by Pinkerton, triumphed in the City of Dunedin and suburban electorates. During his next term Pinkerton used his exceptional committee skills to extend greatly such measures as the Factories Act 1891. He played an important part in enacting new laws regulating the shipping industry, and promoted a masters and apprentices measure to protect the integrity of the skilled trades. The working classes, he insisted, believed themselves crushed down; machinery should uplift rather than degrade labour. Opposition members of the Labour Bills Committee always spoke warmly of the constructive and congenial way in which Pinkerton led them through their work.
Pinkerton was an out-and-out radical democrat. He strongly supported women's suffrage and hoped that its introduction would help remove the 'domineering principle' from marriage. He bent with the temperance gale in an attempt to hold the Workers' Political Committee together and he persistently worked for his labour reforms and local measures. Land policy remained at the heart of his vision of a just society, however. He recognised the need to reserve the best areas for the development of commercial farming but believed that everybody should have the right to own a subsistence plot. Within the Liberal–Labour caucus he consistently opposed the watering down of Liberal land policy, and later claimed that he alone fought the 999-year lease.
In 1896 in Dunedin the coalition of 1890 disintegrated. The prohibitionists, who had grown more militant and demanding, broke their ties with the Workers' Political Committee and ran candidates against the 'labour men' in the general election. Pinkerton lost his seat in the House of Representatives. Richard Seddon, who had succeeded Reeves as minister of labour and who had come to appreciate Pinkerton's loyalty and unobtrusive ability, appointed him to the Legislative Council in early 1897. He soon became chairman of that chamber's Labour Bills Committee. Over the last five years of his life, however, diabetes steadily weakened him. He died in Dunedin on 23 June 1906. His wife and daughters survived him.
Pinkerton's unobtrusive manner may explain why he has not achieved more prominence in the history of the New Zealand labour movement. Yet his contribution was vital. Not only did he direct labour activities in Dunedin but, by gaining election and making his influence and skills available to the 'labour party' in Parliament, he also played a major role in enacting the peaceful revolution which made New Zealand a world leader in social legislation. These political achievements were, of course, his immediate reward. He would not have minded the lack of historical recognition.