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This painting is the last portrait of Britain's first Labour Prime Minister. It was executed in the final year of the Prime Minister's life, two years after his last term in office as the head of a National Government. He had served as Prime Minister four times, although this triumph was bitter-sweet, and the acclaim that he had won as Britain's first Labour Prime Minister was muted by the fact that he later presided over two coalition administrations, and was obliged to make concessions to the Conservatives for which many of his earlier supporters could not forgive him. At the date of this portrait he was serving — or more probably had just ceased to serve — as Lord President of the Council, a sinecure ministry in the government of the Conservative Prime Minister Stanley Baldwin.

MacDonald was born in 1866, at Lossiemouth in Scotland. His origins in no way presaged his remarkable achievements, although a considerable talent for public speaking overcame his lack of a formal education. In 1906 he was elected to Parliament as Independent Labour member for Aberavon. Five years later he became leader of the Party, and on the failure of the Baldwin government in 1924, he became Prime Minister, heading a minority Labour government. This lasted for less than a year, but the novelty of the circumstance was considerable. MacDonald remained leader of his party, and in 1929 he headed a National Government designed to combat the international financial crisis. He remained Party Leader until 1931 and died in 1937.

This portrait is a late example of Lavery's work, and the pairing of painter and sitter, both reaching the end of their careers, is a poignant one. Lavery had painted Macdonald previously, in a portrait of 1931 now in the collection of the National Portrait Gallery, London. In this earlier work the Prime Minister of a National Government strikes a confident pose, leaning against a table, silhouetted against a light, plain background. Here, by contrast, an increasingly ageing and infirm figure emerges from the deep, dark green of the background, and holds the viewer with an experienced and weary gaze. Although described verso as unfinished — MacDonald traveled abroad at the end of 1937 in order to recuperate, on which trip he died aboard a liner bound for South America — the portrait requires no further touches to complete its perceptive grasp of the sitter's character. Lavery had been feted since the 1880s for his brilliance as a society portraitist. By 1937 elegance and brio of his broad-brush technique had been in great demand for over four decades, immortalizing and beautifying royalty and the leaders of early twentieth century Society. The present portrait shows that material success had not diluted his powers or distorted his vision, and the present remains one of the most moving testaments to Lavery''s powers of observation and empathy.