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The phrase "Kilroy Was Here" most likely originated early in World War II by U.S. servicemen who would draw the doodle and text on the walls where they were stationed or visiting. In the United Kingdom it was associated with the U.S. Air Transport Command. It's been said that our GI's scrawled it all over Europe.
Then there's the story that German intelligence found the phrase on captured American equipment. This began leading Hitler to believe that Kilroy could be the code-name of a high-level Allied spy.
At the time of the Potsdam Conference in 1945, it was rumored that Stalin found "Kilroy was here" written in the VIP's bathroom, prompting him to ask his aides who Kilroy was. The fad faded away in the 1950's.
Hartland Plastics of Hartland, Wisconsin manufactured a variety of products from 1939 until 1978. Their first product was this "Kilroy Was Here" figurine. In 1953 they produced many Western figures that were popular on television. Then in 1957 Hartland began making statues of baseball greats of the time.
The Kilroy drawing only illustrates my description and is not included with the figurine.