Green’s Dictionary of Slang

1. (US) to court, to flatter for personal advantage.

1879		P. Rooney Conundrums 63: The average California attorney...hanging around the city prison and ‘heeling the peelers’ in order [to]...gobble up all the paying drunks and enjoy a monopoly of the business of the police court [HDAS].
1912		O. Johnson Stover at Yale Ch. ii: Society piffle...Skull and Bones — Locks and Keys — ...toe the line, heel the right crowd [HDAS].
1934		B. Appel Brain Guy 160: Two men heeling two doll-like dames.
1950		Zanesville (OH) Signal 16 July sect. I 5/1: Father Juniper Serra heeled in with the settlers and sprung missions, presidios and pueblos.
1962		S. Sullivan Shortest, Gladdest Years (1963) 177: Think what good pals we’ve been. Ever since heeling.
1974		J. Lahr Hot to Trot 119: I was heeling the News. That takes a lot of time.

2. (US Und.) to rob a store using an accomplice to distract the clerk or cashier.

1929		E. Booth Stealing Through Life 122: I learned that he and his girl had been out ‘heeling’ on a store. She entered and occupied the clerk in conversation; Red sneaked behind the counter and stole the cash-box.
1968		J. Colebrook Cross of Lassitude 101: The termites of the life [...] who ‘heel’ and ‘boost’ in stores.

3. (US) to cheat a hotel or similar establishment by sneaking in another person without registering; thus heeling n.

1931		D. Maurer ‘Circus and Carnival Argot’ Lang. Und. (1981) 31: (To) heel a hotel...To slip into the room of a friend who is staying at a hotel in a single room .
1950		Goldin et al. DAUL 94/1: Heel a joint... To cheat the landlord by allowing others to sleep in quarters where rent is paid for one or two.
1962		C. Clausen I Love You Honey, But the Season’s Over 82: ‘We’ll round up two more girls and heel it.’ [...] ‘Heeling,’ she explained, was a standard circus expression and practice – slipping extra, unregistered occupants into a hotel room.
1974–75		F. Powledge Mud Show 146: One guy would...rent a room, and about fifteen or twenty of them would heel the joint. You know, all of them sleep there and only one pay [sic] for it [HDAS].