rolling, n.¹ — Green’s Dictionary of Slang

rolling n.¹

[roll v. (1); DSUE and the OED both have v. roll, to rob, esp. of a drunk, as 19C; but Copeland, Hye-Way to the Spittel House (c.1531) offers ‘Taverners that keep bawdry and polling/Marring wine with brewing and rolling’, thus poss. earlier, though equally poss. it means simply rolling the barrels and over-fermenting the wine]

a robbery; note queer-rolling under queer n.

1953		W. Brown Monkey On My Back (1954) 90: Pepe could be setting me up for a rolling.
1955		E. Hunter ‘The Jungle Kids’ in Jungle Kids (1967) 119: They knew about the muggings and rollings.
1968		J.Q. Wilson Police Behavior 182: [A]rrest prostitutes and you reduce the number of rollings.
1977		D. Powis Signs of Crime 199: Rolling Stealing from a man bemused by drink, from an unconscious person, or from one engaged in sexual intimacies.

rolling n.1

rolling n.¹