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.