Analysis of information sources in references of the Wikipedia article "Boot" in English language version.
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It's been widely suggested that the "bootstrap" metaphor originated in the legendary tales of Baron von Münchhausen. As Chris Waigl recently pointed out on the Eggcorn Database (commenting on "boots-trap"), the original German version has a scene in which Münchhausen gets out of a swamp by pulling on his own hair. In an American retelling (supposedly), the Baron uses his bootstraps to pull himself out of a similar predicament. None of the 19th-century cites I've seen allude to the Münchhausen story -- instead, they often refer to pulling oneself over a fence or up a steeple. So if Münchhausen really pulls himself up by his bootstraps in an American version (which I have yet to verify), then the writer probably took advantage of preexisting imagery for an absurdly impossible task.