Green’s Dictionary of Slang

1. a cheater, a fraudster.

1822		D. Carey Life in Paris 89: I [...] shall begin my hasty epistle by expressing my heartfelt joy to learn that you are now out of reach of the sharp-shooters.
1867		J. Poole Ye Comedie of Errors Act I: Among these knowing white folks and sharp shooters.
1896		G.M. Fenn Sappers and Miners 64: Ho! You’re precious cunning. But never you mind, my young sharpshooter.
1928		J. O’Connor Broadway Racketeers 103: A sharpshooter spots his man and labels him for a possible touch.
1937		C. Drew ‘The Chameleon’ in Bulletin 3 Nov. 4/1: [T]here was some sharpshooters on the flat. There was blokes who ran blackboard totes, monkey-sweep men, tip-sellers, under-and-over merchants, three-board artists and Yankee-sweat men, all combined in a frontal attack on the geese with the golden eggs.
1949		R. Chandler Little Sister 187: We’ve got the big money, the sharp shooters, the percentage workers.
1953		A.J. Liebling Honest Rainmaker (1991) 120: Crums, bums and sharpshooters in large numbers.
1975		L. Rosten Dear ‘Herm’ 291: That canard began in China, by some sharpshooter who palmed off 5,000 grasshoppers to a war-lord.
2000		Guardian Guide 29 Apr.–5 May 5: The local accents encourage victims across America to think they’re dealing with a sharp-shooter wearing a suit.

2. a professional gambler.

1917		Van Loan ‘The Last Chance’ in Old Man Curry 106: If he stays around here these sharpshooters will have his shirt.
1929		E. Dahlberg Bottom Dogs 147: He recollected how deep he was in it to that sharp-shooter Skinny.
1933		W.R. Burnett Dark Hazard (1934) 112: With Jim King in the 1 box a lot of the sharpshooters would bet on him, figuring that there might be a jam at the first turn and that he might get clear.
1949		Monteleone Criminal Sl. (rev. edn).

3. (also sharpy) a womanizer.

1922		Appleton Post-Crescent (WI) 11 May 13/4: Flapper Dictionary sharpy – A young Beasel Hound who tries to imitate a Sharpshooter. [...] sharpshooter – A good dancer who spends his money freely.
1929		J. Lait Broadway Melody 77: They think becus nobody ever hit ’em, there ain’t no sharpshooters what can.
1967		M. Anthony Green Days by River 44: That Joe is a sharp-shooter!
1983		R. Klein Jailhouse Jargon and Street Sl. [unpub. ms.].

4. (US Und.) a successful criminal.

1933		Ersine Und. and Prison Sl.
1938		J.E. O’Donnell ‘Overcoat Bennie’ in Mss. from the Federal Writers’ Project 🌐 He’d [...] turn it over to his old friend Sam Pinelli, the pawnbroker, a sharpshooter with whom he had staged many a shady deal.
1942		Berrey & Van den Bark Amer. Thes. Sl. §461.4: clever crook, sharpie, sharpshooter.

5. (US) an expert; one who cannot be fooled.

1933		R. Chandler ‘Blackmailers Don’t Shoot’ in Red Wind (1946) 119: I’m getting me a .25 with copper slugs. A sharpshooter’s gun.
1941		N. Davis ‘Don’t Give Your Right Name’ in Goulart (1967) 24: Some sharpshooter is always rapping suckers for their nickels.
1956		‘Ed Lacy’ Men from the Boys (1967) 66: If the restaurant is a sharpshooter, when he feels the wholesaler is trying to goose him, he switches to a new one.

6. (US drugs) a narcotics addict; cit. is attrib.

1957

J. Blake letter 15 July in Joint (1972) 103: He’d gotten into the sharpshooter mob, the ones who lived only for the next fix.