From the word Jank meaning messed, screwed or fucked up. This is a person who walks around like hot shit on a golden platter but acts more like a cold turd on a paper plate.
Janksterr is a word used to describe someone way passed Gangster. It's a whole new level of coolness. It gives new meaning to people who are called J's.
"Hey look at those converse!"
"man those things are Janksterr."
Or.
"Man I just joined a gang."
"Well I'm a part of the janks."
"What's that?"
"Loser"