With the German invasion of Russia in the autumn of 1941, a "Red Cross Aid to Russia Fund" was established to address the suffering of the Russian people. Clementine Churchill was appointed Chairman and rallied support from celebrity musicians and the wealthy together with factory workers and anyone willing to knit scarves and gloves. By the end of the Second World War £8 million had been raised and her work for the "Red Cross Aid to Russia Fund" is considered one of Clementine Churchill’s greatest achievements. In June 1946 she was made a Dame for her work. She was also awarded the Order of the Red Banner of Labour, a Soviet decoration, and the Distinguished Red Cross Service Badge from the Soviet Red Cross.

The present piece was donated by the artist, via a Mr Love, for an auction held on 12 September 1942 as part of "the Grand Magical Entertainment". A typed letter signed ("Clementine S. Churchill") addressed to Mr Love provides an opinion on the piece and states "I am so grateful for this help, and I hope the caricature may fetch a good price" (1 page, 10 Downing Street, 7 September 1942).

Gilroy (1898-1985) is today chiefly remembered for his Guinness advertisements. His first poster for Guinness dates from 1940 and he continued to produce Guinness drawings for well over twenty years. During the 1920s Gilroy began to build a reputation as a painter both of landscapes and portraits. The National Portrait Gallery holds two examples of his portraiture.