Green’s Dictionary of Slang

1. an entrepreneur, an ‘operator’, thus v. wheeler-deal, to create schemes, ideally beneficial/ profitable to oneself.

1954		N.Y. Times 20 July 18: (ProQuest Historical Newspapers) More power to these Texas ‘wheeler-dealers.’.
1967		P. Thomas Down These Mean Streets (1970) 202: There was a short go of heroin on account of some big wheeler-dealer with millions of dollars’ worth of the stuff had gotten himself busted and this caused a bad shortage.
1971		B. Moyers Listening to America 270: Bott was a grabber, a wheeler and dealer.
1977		B. Davidson Collura (1978) 162: John was a high-class wheeler-dealer in heroin.
1989		R.G. Barratt ‘Tall Poppies Deserve Short Shrift’ in What Do You Reckon (1997) [ebook] He’s supposed to be a hot-shot wheeler-dealer.
1987		R. Campbell Alice in La-La Land (1999) 161: The club-house at La Costa, where, during tournament time, the wheeler-dealers bellied up until the small hours of the morning.
1999		N. Cohn Yes We Have No 76: He used to be a [...] conman, a wheeler and dealer.
1999		Indep. Mag. 3 July 38: Wheeler-dealers in suits use Claridge’s during the day.
2000		S. Travers Tomorrow To Be Brave 131: [W]atching belly dancers take the floor and fat pashas wheeler-dealing at the tables.
2014		E. Pruitt ‘Houston’ in ThugLit Mar. [ebook] Imagine him: the wheeler and dealer.
2108		(con. 1950s) M. McGrath Pie & Mash 134: Bit of a chancer is Charlie. Bit of a wheeler-dealer, bit of a Jack the Lad.
2021		J. Ellroy Widespread Panic 96: ‘She’s sub rosa with this wheeler dealer, Mike Todd’.

2. attrib. use of sense 1.

1969		J. Crumley One to Count Cadence (1987) 171: A gangster was better than a snappy, wheeler-dealer preacher because the gangster was more honest.
1972		Milner & Milner Black Players 247: A politician, religious leader or wheeler-dealer businessman who ‘pimps off the public at large.’.
2000		Observer Screen 23 Jan. 27: Andrew Oldham, wheeler-dealer manager of the Rolling Stones.

3. (Aus.) a petty confidence trickster.

1967

‘Whisper All Aussie Dict.’ in Kings Cross Whisper (Sydney) xliii 11/2: wheeler dealer: A petty confidence trickster.