Green’s Dictionary of Slang

1. (US) a robber who specializes in stealing from drunk, drugged or otherwise incapacitated victims.

1913		Day Book (Chicago) 6 May 26: A jack-roller [...] hangs around a tough saloon, gets a drunken man who is too drunk to take care of himself and robs him.
1917		New Republic 9 137: Theodore H. Martin, ‘hustler,’ ‘jackroller’ and repeater of Kansas City, Missouri. Mr. Martin’s regular business is to wait for jovial drinkers [etc.].
1923		N. Anderson Hobo 5: The ‘jack roller,’ as he is commonly called, the man who robs his fellows, while they are 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.
1934		T. Minehan Boy and Girl Tramps of America (1976) 110: Last night some jack roller stole one of Texas’ shoes.
1947		N. Algren Neon Wilderness (1986) 73: Let the jackroller tell us how he done it hisself.
1952		J. Blake letter 27 Jan. in Joint (1972) 31: Tom has been a jack-roller on Clark Street in Chicago, and tells zestfully of sending untold number of ‘marks’ rocketing into oblivion through the use of chloral hydrate.
1966		H.S. Thompson Hell’s Angels (1967) 42: California’s overall crime picture makes the Angels look like a gang of petty jack-rollers.
1989		J. Morton Lowspeak.
1998		K. Anderson Night Dogs 241: The cops were their friends down there [i.e. on skid row], protecting them from jackrollers.

2. (S.Afr.) an individual, usu. one of a gang, who abducts and rapes women; also attrib.

1990		City Press 11 Feb. 3: Jackrollers are not one gang, but youths – aged from 14 years old – getting thrills by hi-jacking or stealing cars and using them to abduct school-girls, often by threatening them with a firearm [...] ‘The jackrollers warn them that if they testify they will kill them when they come out of prison’ [DSAE].
1993		M.N. Williams Kwa-Landlady in Perkins (1998) 173: What about jackrollers? [...] I read in the Sowetan that a two-year-old girl was raped and killed. Pigs like that should be castrated.
1995		(ref. to 1980s) Nowrojee & Manby Violence against Women in S. Afr. 54: The term [i.e. jackrolling] was coined to refer to the forceful abduction of women in the townships by a gang called the ‘Jackrollers’ which operated between 1987 and 1988 in the Diepkloof area. The original Jackroller gang was made up of a network of fewer than ten youths.
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.