Green’s Dictionary of Slang

(US) a Cadillac.

1929		in Journal Amer. Insurance Feb. [HDAS].
1936		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.
1949		L. Hughes Tambourines to Glory II i: Want a ride in my red Caddy?
1956		T. Thursday ‘Dead Men Don’t Move’ in Smashing Detective Stories Jan. 🌐 A dead man was under a new Caddie coupe.
1960		A. Burgess Doctor Is Sick (1972) 151: Rollin’ in manny and lollin’ round in Caddies and over big cars.
1963		A.S. Fleischman Venetian Blonde (2006) 153: I could have been riding off in that Caddie.
1965		H. Rhodes Chosen Few (1966) 120: She handled that Caddy with the same ease she did everything else.
1973		D. Goines Street Players 20: Earl’s laughter rang out sharp and clear. ‘It don’t have to be the Caddie, baby’.
1978		S. King Stand (1990) 389: The man who had been driving the Caddy was slumped over the wheel.
1986		R. Campbell In La-La Land We Trust (1999) 121: Then we get the Caddie over for the new paint job.
1989		C. Hiaasen Skin Tight 65: He hauls Mr Studhunk outside and glues him buck naked to the hood of his Caddy.
1999		Dr Dre ‘Ackrite’ 🎵 Plus, they on the dick cause the Caddy’s plush.
2000		W. Shaw Westsiders 231: So you’re not in the ’84 Caddy any more?
2006		G. Pelecanos Night Gardener 126: The caddy must be his [...] He got the V version, too.
2013		C. Dundas ‘Rightful King of Wrestling’ in ThugLit Nov.-Dec. [ebook] We drove down in my beater Caddie.
2019		S.M. Jones Lives Laid Away [ebook] I made my way across the street to Carlos’s garage to retrieve my rental Caddy.
2023		(con. 1962) J. Ellroy Enchanters 8: A pimpmobile Caddy dragged him against a guardrail and sheared off his feet.