John Zukowksy, a retired but still active historian, recently sent me a bizarre clipping from the Chicago Tribune about a plane semi-faking bombing lower Manhattan in 1916. The short version of the story: DeLloyd Thompson, an early aviator of some note, took off from the airfield at Governors Island, dropped bombs over South Ferry and the Customs House, dropped a “searchlight parachute ball” to light up Battery Park, and then was attempting to drop a bomb on the Woolworth Building except that the timed fuse malfunctioned and blew some holes in his canvas-winged Wright Flier. The reason I say that the bombs were semi-fake is that the only obvious difference between what he dropped and actual bombs was that his contained flare-like material rather than high explosives.
Thompson had similarly bombed Washington DC five nights earlier and apparently had originally planned to make such demonstrations around the country to highlight vulnerability. I have to wonder if the cancellation of the rest of the tour was related to him nearly killing himself.
Governors Island was an army base in 1916, and I don’t see how this could have been planned without acceptance by the army, even if it was passive. The Times article mentions the senior staff saying there would be no flight, but also officers congratulating Thompson when he returned. Note that April 20, 1916 was less than a year before the US entered World War I, and presumably the army would have been paying attention to the use of airplanes in the fighting in Europe.
The Governors Island airfield:
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