The present work was painted during the sittings Sutherland had with Churchill at Chartwell for the commission. Sutherland and Churchill went back and forth about how he was to be depicted, and while Churchill was not an easy sitter, there was a mutual respect and friendship which developed between two fellow artists. The late, low sunshine in Churchill’s study at Chartwell on this day gives his skin a transparency, and the pose is also notably less direct than the final work, lending a charming intimacy and thoughtful vulnerability to the portrayal.

This work is accompanied by Oscar Nemon's famed study for the sculpture of Churchill which stands outside parliament, and also by one of Winston Churchill's own paintings from his stay at the Villa Choisy in Switzerland banks of Lac Léman, which was owned by the banker M. Alfred Kern.