The man, Steven Louie Witt, said that, no, it was not someone signaling the shooters, and no, it had nothing at all to do with the assassination. Instead, he said, it was a message against appeasement of enemies. He hoped to signal his disapproval of what he considered JFK’s forbearance of America’s enemies.
How to signal that? Here’s where it gets complicated. Witt claimed he held up the umbrella as an icon symbolizing the treachery of Neville Chamberlain, the 1930s British prime minister. Chamberlain, who tried to preserve peace with Hitler by ceding him a part of Czechoslovakia (the Sudetenland), became a reviled symbol of appeasement. The self-described Umbrella Man said that he had been identifying appeasement with Chamberlain’s trademark umbrella. The connection to JFK came via his father, Joseph P. Kennedy, ambassador to Britain at the time and an anti-war isolationist.
Only a very unusual 15-year-old American (Witt’s approximate age in 1938) would have strong feelings about a British prime minister’s behavior, and still harbor those feelings a quarter century later. It is even harder to accept that he could believe JFK, himself a young man in 1938, might “get” the message somehow via the umbrella.
Even if we are to accept that Witt really was the man pumping the umbrella on the Grassy Knoll, and even if he was cognizant of Chamberlain, and even if he did think he could get a message to JFK via the Chamberlain affair, we still have a big problem with this claim.
According to John Simkin, a retired British history teacher and textbook author who runs the historical website Spartacus Educational, the umbrella was never the symbol of Chamberlain that the “umbrella man” claimed it was.
“In Britain, there was never any association with an umbrella at all,” Simkin told me. “Everyone had umbrellas and bowlers in those days.” According to Simkin, the only proper symbol for Chamberlain and appeasement was a piece of paper. That was the document he held aloft, with Hitler’s signature to the so-called Munich Agreement—in which Hitler agreed not to seek any further territorial gains in Europe—as Chamberlain famously declared that he had secured “peace in our time.” (In this old newsreel, you can see Chamberlain hold aloft that document.)
Simkin finds the New York Times video’s assertion that the purpose of opening the umbrella and pumping it in the air to signal Munich simply laughable.
More likely, it was exactly what it appeared to be: a method of signaling shooters, perhaps that JFK had been hit, perhaps that he still seemed to be alive, perhaps to keep shooting. Although it was a sunny day, it had rained the night before, and there was a wind, so it would not have been operationally illogical to move forward with using an umbrella. The fact that the New York Times and the establishment in general have never considered the umbrella worthy of real, serious inquiry, tells us that if the umbrella was part of a plot, it was not so bad a choice.