Shortly after World War II, an American colonel and his wife, stationed in London, happened to meet with Sarah Churchill and her then husband Vic Oliver, a music hall comedian of the Milton Berle variety.
Oliver had the unfortunate habit of calling his father-in-law, Winston Churchill, “Popsy,” which understandably did little to endear him to the old statesman. At any rate, Vic and Sarah invited the American couple down to Chartwell one Sunday evening after the two Americans had professed their great admiration for the wartime prime minister.
The Sunday evening at Chartwell started with Churchill glowering and saying very little. But Oliver, who wanted his American friends to see something of the great man in action, tried to spark conversation with this question: “Popsy, who do you think was the greatest statesman you ever knew?”
Churchill, without even looking up, said, “Without a doubt, the greatest statesman I ever knew was Benito Mussolini.”
After some silence by a flabbergasted audience, Oliver made this follow-up query: “But, Popsy, why do you pick Mussolini?”
”Because,” growled Churchill, “Mussolini is the only statesman who had the requisite courage to have his son-in-law executed” (Count Ciano, Italian Foreign Secretary, in 1943).
Source:
Humes, James C. Speaker's Treasury of Anecdotes About the Famous. New York: Harper & Row, 1978. 116, 117. Print.
Further Reading:
World War II / The Second World War
Sarah Churchill / Sarah Millicent Hermione Touchet-Jesson, Baroness Audley
Victor Oliver von Samek / Vic Oliver
Sir Winston Leonard Spencer-Churchill, KG, OM, CH, TD, PC, DL, FRS, RA
There are so many stories about Churchill that would be great source of hilarity on /r/blackpeopletwitter.