Best definition
With the shits
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.
With the shits: define #2
With the shit
Having the ability to shoot anybody in the face if needed to. Being down to do whatever, whenever and having a fuck it mentality.
Terry: What did you do last night?

Robert: I robbed a bank with my niggas to get my bread up.

Terry: Wow weren’t you scared?

Robert: No nigga I’m with the shit

With the shits: define #3
With the shits
Chicago slang, means to be in agreement with something
Are you with the shits tonight?

Yea dude
With the shits: define #4
With the Shit
With the Shit-having drama, bad attitude, in the middle,Breezy
“Man..Your With the Shit, arn’t you??