July 30, 2022

The Art of Being Winston Churchill: Summer in Canada


After five years on the job, Winston Churchill ceased to be Chancellor of the Exchequer following the defeat of the Conservative party in the general election of 1929. With his new leisure time, Churchill decided to embark on an extensive tour of North America in the company of his son Randolph, his brother Jack, and Jack’s son Johnny. They departed for Canada on 3 August aboard the Empress of Australia.

The Churchills’ tour began in Canada in a special railway car provided by the Canadian Pacific Railroad, stocked with everything Winston might need including a stenographic typist. Along the way Churchill stopped to deliver paid speeches. He fell in love with the natural majesty of the Canadian landscape and the “fortunes” it potentially offered.

“Darling, I am greatly attracted to this country,” he wrote to Clementine. Still, the foreign scenery also moved him to morose thoughts about the political climate back home. “I have made up my mind that if Neville Chamberlain is made leader of the Conservative Party or anyone else of that kind, I clear out of politics & see if I cannot make you and the kittens a little more comfortable before I die.”

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Barry Singer is proprietor of Chartwell Booksellers in New York City and author of Churchill Style (2012).

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