Green’s Dictionary of Slang

(US) a bootlegger.

1921		J. Conway in Variety 12 Aug. 4: They [...] go good until they get acquainted with the bootleggers, then their leanin’ up against lamp posts and picking up pebbles to alibi the boots all summer [HDAS].
1947		B. Schulberg Harder They Fall (1971) 191: Drake was an ex-chauffeur for Nick back in his boot days.