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From what I can see swag breaks down like this: back in the 1600s swag meant goods gained by theft, or booty. I saw the word rise again in a similar form in the late 80s when people would get cool little free gifts or promo stuff for attending conferences. After this swag split into to categories. Free promo items, pins, and the second category was more things gotten for free for attending things. at Wow cons there was often rare and incredible swag given only to those in attendance, so gamers began to associate the word swag with rare or really awesome freebies. From there swag moved on to a replacement for anything cool or awesome. The whole swag meaning secretly we are gay thing, well I'm pretty sure that's just gay dudes wishing all the hot pirate dudes in movies were secretly gay. yes, pirates used the word swag as well as booty, I can understand the confusion what with booty being used but that's another misunderstood word for another time
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