Green’s Dictionary of Slang

Caddy n.

also Caddie
[abbr.]

(US) a Cadillac.

[US] in Journal Amer. Insurance Feb. [HDAS].
[US]Mencken Amer. Lang. (4th edn) 579: The automobile thieves who had their heyday in 1928 or thereabout devised a series of terms of their own to designate cars of the various more popular makes and designs, e.g., breezer for an open car, shed for a closed car, front room for a sedan, B.1. for a Buick, caddy (or golfer) for a Cadillac.
[US]L. Hughes Tambourines to Glory II i: Want a ride in my red Caddy?
[US]T. Thursday ‘Dead Men Don’t Move’ in Smashing Detective Stories Jan. [Internet] A dead man was under a new Caddie coupe.
[UK]A. Burgess Doctor Is Sick (1972) 151: Rollin’ in manny and lollin’ round in Caddies and over big cars.
[US]A.S. Fleischman Venetian Blonde (2006) 153: I could have been riding off in that Caddie.
[US]H. Rhodes Chosen Few (1966) 120: She handled that Caddy with the same ease she did everything else.
[US]D. Goines Street Players 20: Earl’s laughter rang out sharp and clear. ‘It don’t have to be the Caddie, baby’.
[US]S. King Stand (1990) 389: The man who had been driving the Caddy was slumped over the wheel.
[US]R. Campbell In La-La Land We Trust (1999) 121: Then we get the Caddie over for the new paint job.
[US]C. Hiaasen Skin Tight 65: He hauls Mr Studhunk outside and glues him buck naked to the hood of his Caddy.
[US]Dr Dre ‘Ackrite’ [lyrics] Plus, they on the dick cause the Caddy’s plush.
[US]W. Shaw Westsiders 231: So you’re not in the ’84 Caddy any more?
[US]G. Pelecanos Night Gardener 126: The caddy must be his [...] He got the V version, too.
[US]G. Pelecanos (con. 1972) What It Was 125: Has that boy shine up his Caddy while he hits that thing.