From A Different World - Forums

I hate the word "Swag".
Mostly because in public schools it was said by bullies.
I
cannot
stand
bullies.
I can't. If someone asked me to forgive one, I couldn't. That being said, I wouldn't wish death on a bully, because one of my close friends died from bullying.

Back on topic, swag is just somewhat annoying for me.

Woa Surf, that's pretty deep. Sorry to hear that..

Blitz, i think the term "swag" came from swagger and after a quick google search this is what popped up;

swag·ger
/ˈswagər/
Verb
Walk or behave in a very confident and typically arrogant or aggressive way: "he swaggered along the corridor".
Noun
A very confident and typically arrogant or aggressive gait or manner