Willkie excelled at speaking before audiences, both large and small, especially if he spoke off the cuff with only a brief outline or notes to keep him on track. He generally fared poorly when he read prepared speeches verbatim. This ability at informal speaking was especially evident when he engaged the crowds that inevitably gathered around him wherever he went. Willkie enjoyed this immensely and did it as often as possible, much to the dismay of his campaign aides trying to keep him on a tight schedule.
I suspect that this is what’s happening in this photograph, although I don’t know for sure because the FDR Library, which provided the photograph, had minimal information about it. The skyscrapers in the background and the large theater marquee lead me to believe that the scene captured here was in New York City. Perhaps it was before or after Willkie’s November 2, 1940, rally at Madison Square Garden.
I especially like this photograph because it shows Willkie as he typically appeared while campaigning: a little disheveled and unkempt (note the damp, rumpled raincoat and the slightly crushed hat). And the expression on the driver’s face is priceless ...
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