One thing I've never understood about the umbrella thing. The words accompanying the picture say:
"The umbrella is a symbol of appeasement, in reference to the umbrella made famous by Britain's Chamberlain."
At that time, it seemed like every single English man from the middle classes up, wore a bowler hat and carried an umbrella. Umbrella's were ubiquitous, almost everyone carried one, so why it became a symbol attached to Chamberlain is baffling.
Chamberlain is infamous for returning from Germany with an "agreement" that Britain and Germany would never go to war, and waving the piece of paper it was written on:
"This morning I had another talk with the German Chancellor, Herr Hitler, and here is the paper which bears his name upon it as well as mine."
The only real act representing Chamberlain's appeasement would be to wave a piece of paper at Kennedy. The umbrella thing is mystifying.
Chamberlain liked to carry a large black umbrella when he went out for walks, et cetera. If you search photos of him you'll see him with one in many of them.
As for the origins of the phrase: In the UK in1940 after Hitler's violation of the Munich Agreement, there was an enormously popular book titled "Guilty Men" by an anonymous author named Cato. The book condemned 15 British figures for their appeasement of Hitler. In it, Chamberlain, condemned as one of those appeasers, is referred to as "the umbrella man".
Also during the 1960 campaign, in an indirect criticism of JFK, LBJ pointedly criticized Joe Kennedy Sr. (he was intensely disliked by the liberal wing of the Democratic party) with this comment: "I wasn't any Chamberlain - an umbrella policy man...I never thought Hitler was right."