Top definition
One who is too poor to support their gangster appearance.
"You got holes in your gear but they ain't from bullets." This is a true "Goodwill Gangster"

by JJB1600 December 04, 2008
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2
A ghetto ass guy who wears clothes with money signs, expensive chains and shoes, acts like he has hoes and money but really lives on foodstamps and shops at Goodwill.
A: I'm a young thug. Look an my new Jordans, yo.

B: Damn bro. They lookin' fresh. Got them money sign pants too.

A: Yeah, bruh. Got the money sellin' weed.
C: Oh my god, you're such a goodwill gangster. We all know you're on foodstamps and shop at goodwill.
by Not_Dylon January 15, 2017
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