July 25, 2023

The Art of Being Winston Churchill: Driving

By BARRY SINGER

One hundred years ago, driving automobiles became central to Winston Churchill’s lifestyle, after he made Chartwell his primary residence, while keeping a modest apartment in London. It should come as no surprise that someone who had flown airplanes with Churchill‘s avidity would drive a car. His daughter Sarah’s recollections confirm that he did. Still, it is hard to imagine him behind the wheel; in the mind’s eye he was always chauffeured.

On 13 August 1923, though, Churchill wrote to Clementine:

“I took Fowler [the chauffeur] with me on Saturday in the little car, and drove all the way….I sent him back by train to get the big car in order. This morning I drove the car back myself alone. It is exactly 50 miles, and we did it in an hour and 55 minutes. I can drive the car quite easily now, which will be a great help in our arrangements. It goes very nicely at 35 miles p. h. & will do 40 easily.”

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The “big car” was a Rolls Royce. The “little car” was a Wolsey two-seater. In 1925 Churchill would trade this Wolsey in for a two-seater De Luxe Landaulette. The following year, he again traded up, adding a cash payment of £500 plus the year-old two-seater for a new Wolsey four-seater Landaulette.

Churchill’s driving skills did not, however, match the quality of his automobiles. Accidents and mishaps frequently ensued. Fortunately for history, his own safety, and the safety of others, Churchill eventually did give up driving himself and employed a full-time chauffeur.

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