While supremely confident and self-assured in most fields of life, Churchill was generally modest about his achievements as a painter; he didn’t aspire to create masterpieces – he never claimed he had ever painted one – and didn’t intend to earn money from his pastime (unlike his other craft of writing). But he did have a certain ambition for his art. In 1921, only six years after he’d first tried his hand with a brush, he is said to have sold up to six paintings he’d exhibited in Paris under the pseudonym Charles Morin at Galerie Druet for the princely sum of £30.00 each. In 1947 he successfully submitted two paintings to the Royal Academy Summer Exhibition under the name David Winter (including ‘Winter Sunshine, Chartwell’, which had won a prize in 1927).
‘To be really happy and really safe, one ought to have at least two or three hobbies, and they must all be real.’
Churchill, ‘Hobbies’, Pall Mall Gazette, Dec 1925 (cited in Langworth, Churchill: In His Own Words)