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Cadillac Draw 

The maximum canteen draw allowed per month in prison.
Ex. 1

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, USA v. 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!
Cadillac Draw by FAIMnatic October 23, 2020

Jump in the Cadillac

Tommyinnits famous thing
Fan: "jump in the Cadillac"
Tommy: "die"

jump in the cadillac

Dono/Donation: “Jump in the cadillac girl put some miles on it”

Tommy: AHAHHAHSHSHDJFISN FUCK YOU FUCK YOU FUCK YOU FUCK YOU

After the dono disappears: OK ANYWAYS

Cadillac Pussy 

This is a very luxurious vagina that a lot of people wish they could own, but only very few people can actually afford. It (the vagina) not only looks fantastic, but also feels exceptional on the inside.
I know that woman has a "Cadillac Pussy" but I just can't afford it.
Cadillac Pussy by Hank Jr. June 12, 2013

the cadillac

A large luxurious handicap stall in a public restroom.
The whole bathroom was empty so I got to use the cadillac.
the cadillac by SirScarface69 August 11, 2010

Black Cadillac 

Just a controversial 2003 American horror film about a group of three young men become terrorized and stalked in a high-speed chase with a mysterious pursuant using a black 1957 Cadillac Limousine, and barely escape with their lives.
"Did you see the Black Cadillac movie?" - Someone who watch that movie
Black Cadillac by Ryan900USAYT November 21, 2022