Chicago term. It means the opposite of lacking. To be "with the shits" means to be in direct possession of enough of physical protection for the amount of illegal merchandise (
work) you are currently attempting to move. On the South Side of Chicago, holding any amount of
work requires at least a sidearm; larger amounts of
work call for additional crew members and more guns. If another crew is able to take your merchandise by force then you are lacking and are not at all with the shits. Popularized by many Chicago rappers, perhaps most notably by Fredo Santana on his track "My Lil Niggaz".
Outside of Chicago, the term has loosely come to mean simply a willingness to engage the types of illegal activities commonly discussed in
popular hip hop
music. If you're actually in Chicago, however, it's important that the original
definition be observed at all times. You absolutely do not want to get caught lacking in the field.
Real
Chicago Hood Nigga #1: Say bruh, ain't you afraid of getting run up on by the opps?
Real
Chicago Hood Nigga #2: Who, me? Hell nah, fuck them pussy ass niggas, my lil niggas with the shits bruh. Shit... I wish they would try to run up, fuck around and get they whole
crew taken out, homie we don't play.