Green’s Dictionary of Slang

1. (also jackhunt) to rob a victim (often one of one’s own companions) while they are drunk or sleeping; thus jackrolling/jack-hunting n. [jack n.² + roll v. (3a); ? poss. underpinned by stereotype of jack n.⁵ (1)/SE hunt].

1913		Day Book (Chicago) 6 May 26: [headline] The Evil of All Kinds of Jack-Rolling, Pickpocketing and Murdering.
1916		J. Lait ‘Canada Kid’ in Beef, Iron and Wine (1917) 152: Firs’ I jackrolled a couple o’ drunks, then I spreads out a little an’ goes after live ones.
1923		N. Anderson Hobo 51: ‘Jack rolling’ may be anything from picking a man’s pocket in a crowd to robbing him while he is drunk or asleep.
1930		C.R. Shaw Jack-Roller 85: My buddy, being an old ‘jack-roller,’ suggested ‘jack-rolling’ as a way out of the delima. So we started to ‘put the strong arm’ on drunks.
1933		‘Goat’ Laven Rough Stuff 14: The three of us organized ourselves into a mob for the purpose of jack-hunting. This is taking a man that’s drunk, either by crowding him in a doorway [...] or you can go through him after putting the sleeve on him, strong-arm stuff.
1947		N. Algren Neon Wilderness (1986) 66: Once he’d lost his cheque at blackjack and had mumbled that he’d been jackrolled.
1958		W. Motley Let No Man Write My Epitaph (1959) 93: Bumming around down there on Skid Row [...] Sometimes jackrolling.
1963		B. Hecht Gaily, Gaily 123: Among the seedy footpads, bellicose drunks, and jack-rolling harlots called to the bar.
1986		L. Heinemann Paco’s Story (1987) 133: Man-oh-man, I just fucking know I’m going to get jackrolled.
1991		(con. 1920s) O.D. Brooks Legs 111: If a cop spots us rousting him, he’ll swear we’re jackrolling and run us in.

2. (S.Afr.) to abduct, then rape a woman, usu. a schoolgirl, to gang-rape; thus jack-rolling n., abducting and raping [despite logical link to sense 1, DSAE suggests a song by Womack & Womack, with lyrics ‘Love is just a ballgame, sometimes you lose – jackroll’].

1990		City Press 11 Feb. 3: More and more schoolgirls are being ‘jackrolled’ — abducted by youths and raped — for up to a week at a time. Police estimate that during the past two years when jackrolling began, hundreds of schoolgirls have been held captive and gang-raped [...] Two Soweto Murder and Robbery policemen ... have arrested some of the worst jackrolling gangs [DSAE].
2000		C. Glaser Bo-Tsotsi 189: By the early 1990s, ‘jackroller’ gangs were rampant in Soweto. ‘Jack-roll,’ in street argot, means to abduct and rape.
2003		R. Beauregard et al. Emerging Johannesburg 115: Mokwena suggests that Jackrolling became something of a male ‘fashion’ among young boys seeking to assert their manhood or toughness.