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Ok, let's break this one down... The sheer lack of understanding and respect for the English language spreading like a stupid wildfire is making me sick. 1) to jack something is slang for "to steal." 2) swag is common slang for "stuff we all get." Generally speaking, the big bag of random and mostly useless crap you get at a convention of sorts. Therefore, "jack my swag" quite literally means to "steal my bag of swag (stuff we all get)" Though, the unfortunate truth of the matter is, this is what people who don't think about what words coming out of their mouths think means "jack my swagger" or to "steal my style".
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