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A Winchester is a person who retells the same jokes [over and over again]. [It started] off as a nickname for a person (We'll call him Dev) who would repeat the same jokes [on a regular] basis, especially on a Jokes page on Facebook. The name comes from the lever-action rifle of that name - this was often called a 'Winchester Repeater'. The nickname stuck and even to repeat a joke now is met with claims of 'Winchester!'
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