Green’s Dictionary of Slang

1. a pickpocket.

1663		Wandring-Whores Complaint title: A full discovery of the whole Trade of [...] Bawds, Whores, Fyles, Culls, Mobs, Budges, Shop-lifts, Glasiers, Mills, Bulkers, [...] and all other Artists, who are, and have been, Students of Whittington Colledge.
1674		Head Canting Academy (2nd edn) 28: A whole gang of rogues, distinguished by Files, Lifts, Gilts, Budges, Runners, Heavers, &c.
1676		A Newgate ex-prisoner A Warning for House-Keepers 6: A File is a Pickpocket, a Bulk is his tame-Rogue, who goes alwaies with the File, for he can do nothing without the File.
c.1698		B.E. Dict. Canting Crew n.p.: File, c. a Pick-pocket.
1705–07		N. Ward Hudibras Redivivus II:5 16: Jilts, Shoplifts, Files and brimstone B—s.
1718		C. Hitchin Conduct of Receivers and Thief-Takers 14: It was my Opinion they were inclinable to turn Files, (alias Pick-Pockets).
1728		J. Dalton Narrative of Street-Robberies 28: As to Hulks, Finebones, Black Isaac, &c. they were but Under-strappers, tho’ Black Isaac could Bite a Clout, as dexterously as any File in Town.
1737, 1759, 1760, 1776		Bailey Universal Etym. Eng. Dict. n.p.: A file, or Bungnipper, Pick-pockets, who generally go in Company with a Rogue, called a Bulk or Bulker, whose Business ’tis to jostle the Person against the Wall, while the File picks his Pocket; and generally gives it to an Adam Tiler, who scowers off with it.
1747		Life and Character of Moll King 12: harry: But who had you in your Ken last Darkee? moll: We had your Dudders and your Duffers, Files, Buffers, and Slangers.
1754		Scoundrel’s Dict. 18: Partners to Files – Shoulder-shams. [Ibid.] 29: The File is the same as the Diver, tho’ for the most part he goes without the Bulk, and was formerly known by the Title of the Bung-nipper, because of a horn Thumb and sharp Knife, he used to cut the Pockets clean off, with all that was in them.
1768		(con. 1710–25) Tyburn Chronicle II in Groom (1999) xxvii: A File A Pick-pocket.
1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue.
1790		‘The Bowman Prigg’s Farewell’ in Wardroper (1995) 283: Then aideu to all kins and knots, / To kid-layers, files and trapanners.
1812		Vaux Vocab. of the Flash Lang. in McLachlan (1964) 240: File, in the old version of cant signified a pockpocket, but the term is now obsolete.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.
1859		Matsell Vocabulum 32: file A pick-pocket. The file is one who is generally accompanied by two others, one of whom is called the ‘Adam tyler;’ and the other the ‘bulker,’ or ‘staller.’.
1860		Hotten Dict. of Modern Sl. etc. (2nd edn).
1873		Sl. Dict.
1931		Irwin Amer. Tramp and Und. Sl. 72: File.–A pickpocket.
1949		Monteleone Criminal Sl. (rev. edn).

2. a shoplifter.

1753

J. Poulter Discoveries (1774) 29: To caution all Shopkeepers and Salesmen against Shoplifters of both Sexes [...] There shall be generally three Persons together, called in Cant Prigger Lifts or Files [...] They will open a Piece of Stuff and hold it up between the Owner and their Partner that sits down with her Petticoats half up ready for the Word nap it; then she puts it between her Carriers (that is, a Cant Word for Thighs) and then gets up and lets her Clothes drop [...] and so walks off.

3. (also old file upon the town) an experienced fraudster or confidence trickster.

1812		Vaux Vocab. of the Flash Lang. in McLachlan (1964) 240: file: a person who has had a long course of experience in the arts of fraud, so as to have become an adept, is termed an old file upon the town; so it is usual to say of a man who is extremely cunning, and not to be over-reached, that he is a deep file.
1821		‘An Amateur’ Real Life in London I 141: †Old files—A person who has had a long course of experience in the arts of fraud, so as to become an adept in the manoeuvres of the town, is termed a deep file—a rum file, or an old file.
1830		Lytton Paul Clifford I 147: A middle-aged man, though a very old ‘file,’ who was sentenced for getting money under false pretences.
1836		Morn. Post (London) 7 June 4/2: I find that he has lived upon the report of 25,000l. [...] its all nonsense. he is a regular old file upon the town.
1845		‘Fight with Snapping Turtle’ in Martin & Aytoun Bon Gaultier Ballads 65: The old experienced file [...] Answered with a quiet smile.
1857		Thackeray Virginians I 188: Will is an old file, in spite of his smooth face.

4. an artful, cunning or shrewd person, a man, a ‘fellow’; thus old file, an old and/or experienced person.

1821		W.T. Moncrieff Tom and Jerry II iv: Well, I’m off – you’re a good old file – I’ll give you a shilling for luck.
1832		Egan Bk of Sports 160: Into the space tom ol— , the clever file, / Has stakd’ and rop’d, and made for boxer’s fit.
1836		Westmorland Gaz. 9 Dec. 8/6: If you are a cunning old file [...] With money to rent and to buy land [...] Why, your fortune is made.
1847		‘Epistle from Joe Muggins’s Dog’ in Era (London) 24 Jan. 4/1: [H]e’s a cunning old file, and chisels the green ones who want to sport their pound or two on a race beautifully.
1853		R.S. Surtees Mr Sponge’s Sporting Tour 133: Frosty’s a cunning old file.
1860		Essex Standard 28 Mar. 3/5: There were a few rum old files.
1877		J. Greenwood Dick Temple I 57: ‘What kind of fellow is the cabman, Jack?’ ‘An old file, and well up to his work.’.
1891		A. Day Mysterious Beggar 333: Oh you old snoozer! [...] Wouldn’t I mop th’ floor with ye! Ye ugly old file!
1900		Sporting Times 13 Jan. 6/3: The knowing old file in Pretoria / Caught the ‘Stater’ with visions of gloria.
1906		Marvel 9 June 552: He’s a decent old file, Frank, you know.

5. a pickpocket’s assistant.

1848

‘Ned Buntline’ Mysteries and Miseries of N.Y. I 13: Why, warn’t none of the files on the tramp?