The state of not being pimpin', but owning a cadillac anyhow. ie. doin' it like a small-timer, aka a "shrimp"
Person1: Man, look at that cadillac! I bet that guy gets tons o' ass. He's cadillac pimpin'. I wish I had a cadillac.
Person2: Naw, man- he's cadilac shrimpin'. His girlfriend sucked my dick last night in my VW Rabbit. Maybe he should pimp harder.
Person1: What a sucka
Prosecutor: What was the amount of money that was sent by a money order here?
Enriquez: $60, about the maximum canteen draw allowed per month, what we call a Cadillac draw.
Rene 'Boxer' Enriquez, USAv. Jaimez, September 12, 2018.
Ex. 2
Lil Smiley: Odelay vato! Just paid a visit to the canteen! I got six soups, five candy bars, four bags of chips, three mints, two packs of gum, and a partridge in a pear tree!
Spider: Damn fool! You pulled a Cadillac Draw! I'll trade you a couple fuck books and a fifi for the candy bars!