A friend sent me a Dunhill feature from the Daily Telegraph, stating that Churchill occasionally smoked a pipe as a holiday from cigars: “I can find no reference to him having ever smoked a pipe, can you?”
I think Dunhills are stretching. I can find no testimony to Churchill ever smoking a pipe. There are indications that he deplored pipe smoking (though he tolerated it from Sir Arthur Tedder). Perhaps this arose through his antipathy (which grew in the early 1930s) to Prime Minister Stanley Baldwin.
By looking for Baldwin references, I found a key cigar-and-pipe standoff between Churchill and “SB” in 1924, when they were on better terms, in Martin Gilbert’s Winston S. Churchill, vol. 5, page 59 quoting Churchill (from an unpublished note) after the 1924 general election, when Baldwin was forming his new Conservative government:
I was shown into the Prime Minister’s office. After a few commonplaces I asked him whether he minded the smoke of a cigar. He said “No,” and pulled out his famous pipe. Then he said “Are you willing to help us?” I replied guardedly, “Yes, if you really want me.” I had no intention of joining the Government except in some great position, and I had no idea—nor had anyone else—what was in his mind. So when he said, “Will you be Chancellor of the Exchequer?” I was astonished. I had never dreamed my credit with him stood so high….I should have liked to have answered, “Will the bloody duck swim?” but as it was a formal and important conversation I replied, “This fulfils my ambition….”
I suppose at the point Churchill would have happily smoked Baldwin’s pipe himself.
There are also indications that he deplored Virginia cigarettes, though he smoked cigarettes early in his youth. In Paul Reid’s manuscript for Defender of the Realm 1940-1965, the upcoming third volume of The Last Lion, which read for Mr. Reid, is a comment from Churchill’s private secretary Jock Colville, after WSC had failed to bring the Turks into World War II. Colville found WSC puffing a Turkish cigarette—the one and only time he’d ever been seen with one. Gesticulating with it, Churchill said, “It’s the only thing I ever got from the Turks.”