Green’s Dictionary of Slang

1. (orig. US) a cyclist.

1880		Scribner’s Monthly (N.Y.) XIX 496: In the parlors the costumes of the wheelmen seemed not so much out of place as they were pleasing.
1884		Century mag. (N.Y.) Sept. 646: As wheelmen nowadays so greatly abound, the landlords profit by the arrangement .
1889		Worcester Jrnl 27 Apr. 5/1: The scorcher is he who tries to make the pace hot for any wheelman who may be in his company.
1895		Truth (Sydney) 7 Apr. 3/4: Then the wheelman concluded that he had committed enough murders and sold his bike, and took unto himself a wife.
1896		S. Crane in Sun (N.Y.) 5 July in Stallman (1966) 150: The truck driver resolves in his dreadful way to make life as troublous and thrilling for the wheelman as he can.
1901		Boy’s Own Paper 13 Apr. 441: This town was a great resort of wheelmen a few years since [...] But level open roads have their disadvantage to the touring cyclist.
1904		Sydney Sportsman (Surry Hills, NSW) 2 Nov. 1/1: ‘Wheelmen are warned that competing in unregistered races [...] will be met with 12 months disqualification’.

2. (orig. UK Und., also wheel, wheelsman) an expert car driver, either for the police or for criminals.

1947		N. Algren Neon Wilderness (1986) 226: Wasn’t he Gino? The best wheelman on the Near Northwest Side?
1952		C. Hamilton Men of the Und. 144: Take a wheelman, put him with a brace of rodmen, provide a lucrative mark.
1960		P. Rabe My Lovely Executioner (2006) 45: I didn’t know what a wheelman was but it sounded professional. [Ibid.] 125: I didn’t know who the wheel was.
1971		T. Thackrey Thief 289: You need a wheel-man.
1985		J. Wambaugh Secrets of Harry Bright (1986) 34: Hiram was wheelman for the famous stopwatch bandit! Moms Murphy was actually kind of proud.
1990		(con. early 1950s) J. Ellroy L.A. Confidential 54: Perkins is an ex-con wheelman who fucks dogs.
1996		P. Howard The Joy (2015) [ebook] We hop into the car and speed off, with Rods doing justice to his reputation as a good wheels man.
2004		N. ‘Razor’ Smith A Few Kind Words and a Loaded Gun 8: Tommy, the wheel-man, had a background in cannabis cultivation.
2008		Simon & Burns ‘More with Less’ Wire ser. 5 ep. 1 [TV script] Who’s gonna be our wheelman?
2009		T. Black Gutted 106: Mac might have made a wheelman in another incarnation.
2010		L. Berney Gutshot Straight [ebook] ‘I’m a wheelman. Getaway driver’.
2013		T. Black ‘Too Close to Call’ in Killing Time in Las Vegas [ebook] I was no wheelman, but I’d lost them [...] they were waiting — two cops.
2013		F. Bill Donnybrook [ebook] ‘You rob a bank or something? Tig tells that you’s a helluva wheelman’.
2020		S.A. Crosby Blacktop Wasteland 201: ‘I guess the kind of shit they into don’t really require wheelmen’.

3. (US Und.) one who operates a crooked roulette wheel at a carnival.

1922

El Paso Herald (TX) 18 July 13/6: The circus grafters are the shell and wheel men, flat-joint and broad workers, stalls and dips.