Green’s Dictionary of Slang

1. (orig. US) a cheat, a swindler; a petty criminal.

1849		Dublin Eve. Mail 19 Mar. 3/2: He engaged a car-man [...] to drive to a certain hotel. [...] Here the ‘chiseller’ adopted the name of ‘Sir Charles Henry Bentinck’.
1875		Donaldsville Chief (LA) 29 May 1/6: Story, the sculptor, is making a sensation in Florence, Italy, by his impersonation of Shylock, was also a chiseler.
1918		C. Mackenzie Sylvia Scarlett 158: You know I won the toss. We tossed up which should tell and I won. You are a chiseller.
1928		J. O’Connor Broadway Racketeers 94: Many of the crude chiselers never strike the happy medium.
1929		D.H. Clarke In the reign of Rothstein 13: A ‘chiseler,’ to Broadway, is a chap given to sharp practices even with those who trust him.
1930		J. Lait Gangster Girl 4: The Chicago outfit were chiselers.
1931		G. Milburn ‘Convicts’ Jargon’ in AS VI:6 437: chisler, n. A petty larceny thief; a minor gangster.
1934		R. Chandler ‘Finger Man’ in Pearls Are a Nuisance (1964) 115: I suppose you two chisellers think that’s all I care about.
1939		J. Weidman What’s In It For Me? 79: I found out what it meant to have eight chisellers fighting and conniving.
1941		N. Davis ‘Don’t Give Your Right Name’ in Goulart (1967) 1: How are you, you chiseler? [...] Robbed any starving widows today?
1947		J. Symons Man Called Jones (1949) 53: The cheap chisellers’ tricks played on old women.
1951		M. Spillane One Lonely Night 24: He was no use for chisellers or the spoils system.
1952		Lait & Mortimer USA Confidential 9: The chiselers, with no independent means of their own, all made the same boner.
1959		M. Richler Apprenticeship of Duddy Kravitz (1964) 88: I’m no chiseller.
1960		J. Havoc Early Havoc 17: Mr Dankle was out to clip people [...] He wasn’t just a little chiseller; he was a big-time chiseller.
1962		Ragen & Finston World’s Toughest Prison 794: chisler – A petty thief; a cheap gambler; an intruder.
1963		M. Spillane Return of the Hood 53: I can chisel the chiselers and don’t have to pay any respect to the phony politicos.
1973		G.V. Higgins Digger’s Game (1981) 95: I always knew he was a god-damned chiseler.
1975		‘P.B. Yuill’ Hazell and the Three-card Trick (1977) 97: They were only a couple of smalltime chisellers.
1978		F. Norman Dead Butler Caper 139: You may be absolutely certain of that, you ghastly little chiseller.
1981		S. King Cujo (1982) 222: You welfare chiseler.
1991		B. Hamper Rivethead (1992) 9: He broke said pool stick over said chiseler’s head.

2. (US) a miser; one who does not pay their share.

1926

Judge (NY) 91 July-Dec. 31: Chisseler - Tight-wad.

3. (US und.) one who drums up business for a bail bondsman or for bondsmen.

1932

Seabury Report 104: A ‘chiseler’ is a man employed by one of the individual bail bondsmen in the Magistrates’ Courts, comparable to the ‘runner’ who serves a lawyer. In many instances, however, he works independently, peddling his business to various bondsmen or brokers who will bargain with him for it, and selling it to the highest bidder.