A recent book by a distinguished historian suggests that Winston Churchill disdained common people. It cites another Prime Minister, H.H. Asquith, during World War I, providing a tow to a broken-down motorist and giving two children a lift in his car. The writer adds: “It is hard to imagine Winston Churchill behaving in such a fashion.”

It is not hard at all. In fact, Churchill did frequent kind things for ordinary people he encountered, privately and without fanfare. We know about them only through his private correspondence, thanks to the official biography, Martin Gilbert, or the testimony of observers.

A prominent example is the gypsy couple Churchill befriended in Westerham. Grace Hamblin, longtime Churchill secretary and first administrator of Chartwell, recalled them in a 1987 speech to the International Churchill Society:

 There was a funny old gypsy living in the district, called Donkey Jack, because he had a donkey and trap, and a wife and a dog. My father, who was a farmer, called him a parasite, because he lived on stolen potatoes, strawberries and apples. But Sir Winston had a more romantic view. He thought it was wonderful. When Donkey Jack died, and his donkey had to be destroyed, there was nowhere for poor Mrs. Donkey Jack to go. It wouldn’t be safe for her to live on common land. Sir Winston allowed her to live in his wood, in a little gazebo which had been there for years, full of earwigs and that sort of thing, but she loved it. It would have been stupid to offer her a house because she wouldn’t have understood it. He knew just what would give her pleasure.

In 1935, Mrs. Donkey Jack suffered a fractured ankle. Churchill sent her to hospital for treatment, but, realizing her camp and her two dogs would be left unattended, asked his gardener Arnold to look after them.

“Should the worst be realized I shall try and get her into a decent home,” Churchill wrote his absent wife. “Meanwhile her savage dog (the little one) still stands a faithful sentry over her belongings. He allows Arnold to bring food at a respectable distance and consents to eat it, but otherwise he remains like the seraph Abdiel in Paradise Lost:

 ‘Among innumerable false, unmoved;

Unshaken, unseduced, unterrified;

His loyalty he kept, his love, his zeal.’”

continued in part 2…