Green’s Dictionary of Slang

1. (US) a large clumsy shoe.

1938

D. Runyon ‘A Very Honorable Guy’ in Runyon on Broadway (1954) 415: He only thinks the old gondolas are a little heavy to shove around.

2. (US Und.) a large stolen automobile.

1931		G. Milburn ‘Convicts’ Jargon’ in AS VI:6 438: gondola, n. A stolen sedan.
1935		J. Conroy World to Win 282: Me and the boy rid that gondola for twenty-six hours.
1950		Goldin et al. DAUL 84/1: Gondola. 1. A stolen sedan. 2. (Hobo) A low, open freight-car.