evidence: Churchill on the Optimist and the Pessimist [...] Question: Referring to your posts of quotations Churchill never said, do you know who actually did say "A pessimist sees the difficulty in every opportunity; an optimist sees the opportunity in every difficulty"? I find no attribution other than to Churchill. [...] Like many "red herrings," the optimist/pessimist quote is all over the web ascribed to Churchill–and not one of those appearances offers a source (speech, book or whatever). If he said it, no one has produced the source.