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Bernard Hailstone’s 1955 portrait is recognised to be the last officially commissioned portrait of Winston Churchill. In the previous year, the artist Graham Sutherland had completed the ugly portrait that both Sir Winston and Lady Churchill disliked so much the latter destroyed it. Hailstone’s manner provoked no such distaste. It is recorded that Lady Churchill liked the Hailstone image so much, by contrast, that she sent the artist a note to that effect.

When the Cinque Ports commissioned a portrait of Churchill as their Lord Warden and Admiral, the Prime Minister sat to Hailstone during 1955 at his house at Chartwell. The artist records that his sitter:
‘was very affable and pleasant, but difficult to work on because he wouldn’t keep still! He was dictating his history of the English Speaking Peoples while I was painting. He didn’t want to waste any time. He was a jolly good painter. I was very impressed with his work.’

The first product of these sittings must he this study of Sir Winston, head and shoulders, still wearing into retirement his characteristic ‘siren suit’, the utilitarian one-piece garment that he had invented in the war as a more practical solution than a normal suit to the problem of dressing in a huny during an air raid.

This image, with its head slightly downcast is a magnificent piece of painting, and an insightful glimpse of one of the most remarkable and dynamic men of his century in his eighty-first year. The age of the sitter is not disguised, nor is the fact of his retirement, but the pugnacious set of the head and clear gaze recall at once Churchill’s keen intelligence and indomitable character.