Green’s Dictionary of Slang

1. a confidence trickster who used a (spurious) knowledge of astrology to help to convince his or (more often) her victims; the preferred swindle was the ‘miraculous’ recovery of stolen goods.

1614		Jonson Bartholomew Fair I ii: Sir, my mother has had her nativity-water cast lately by the cunning men in Cow-lane, and they ha’ told her her fortune.
1754		Trial of Elizabeth Canning in Howell State Trials (1816) 485: I was wringing my hands and tearing about, and she advised me to go to the cunning man [ibid.] 493: What cunning man was that that lived in the Old-Bailey?—He used to tell fortunes.
c.1786		Grose Classical Dict. of the Vulgar Tongue ms. additions n.p.: Cunning Man a Cheat who pretends by his Skill in Astrology to assist persons in Recovering Stoln Goods, & also to tell them their future Fortune, as when, how often & to to wjhom they shall be married, &c.
1788, 1796		Grose Classical Dict. of the Vulgar Tongue (2nd, 3rd edn) n.p.: Cunning Man. A cheat, who pretends by his skill in astrology to assist persons in recovering stolen goods: and also to tell them their fortunes, and when, how often, and to whom they shall be married; likewise answers all lawful questions, both by sea and land. This profession is frequently occupied by ladies.
1811		Lex. Balatronicum.
1821		Morn. Chron. (London) 18 Oct. 3/1: The Cunning man could not, with all his foresight, forsee the work that was about to take place.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.
1851		Hants Advertiser 26 Apr. 2/6: [headline] Conviction of the ‘Cunning Man’ of Rolvendon.

2. a trial judge.

1785		Grose Classical Dict. of the Vulgar Tongue n.p.: Fortune teller, or cunning man, a judge, who tells every prisoner his fortune, lot, or doom; to go before the fortune teller, lambskin man, or conjuror, to be tried at an assize.
1796		Grose Classical Dict. of the Vulgar Tongue (3rd edn).
1811		Lex. Balatronicum.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.

a clever cheat.

c.1698		B.E. Dict. Canting Crew.
1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue n.p.: Cunning shaver, a sharp fellow, one that trims close, i.e. cheats ingeniously.
1802		Morn. Post (London) Alderman Curtis’s Barber takes all the credit fore the punctuality with which his master’s Government Securities are always paid. Clerks in office never trifle with a cunning shaver: .
1811		Lex. Balatronicum.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.
1828		Belfast News Letter 15 Jan. 1/4: Allan, who had bustled up from a barber’s shop into a bookseller’s, was a ‘cunning shaver’.
1846		Hants Teleg. 4 July 6/6: Faugh! Captain Seaver, you cunning shaver. You gay deceiver.
1861		Dundee, Perth & Cupar Advertiser 22 Mar. 4/5: The aggrieved party instantly acted [...] and knocked the cunning shaver into a bedroom.
1862		E. de la Bédollière Londres et les Anglais 313/2: cunning shaver, [...] filou dont les ruses sont habilement combinées.

(N.Z.) very cunning.

1926		J. Cowan Travel in N.Z. II 63: ‘As cunning as a Maori hen’ [i.e. weka] is a familiar New Zealand bush simile.
1947		D. Davin For the Rest of Our Lives 239: Innocent as a child and cunning as a Maori dog, Bert had once called him.
1953		M. Scott Breakfast at Six 30: ‘Cunning as a Maori dog’, supplemented Sam vulgarly.
1959		G. Slatter Gun in My Hand 91: Cunning as a Maori dog. Too right he is.
1962		Australasian Universal Dict. I: ‘As cunning as a Maori dog’ is a common simile in New Zealand, although there is not the same local flavour in the slang there.
1972		M. Hayward Diary of the Kirk Years (1981) 30: He’s told us about being at a Maori gathering when a pakeha said unthinkingly, ‘He’s as cunning as a Maori dog’. It appeared to have gone unnoticed until a Maori remarked, ‘He’s as cunning as a pakeha dog’ [DNZE].
1988		McGill Dict. of Kiwi Sl.
[1995		Dominion (Wellington) 7 June 44: He denied a magazine article which questioned Tatarangi’s will to win. ‘I’d say that [another Maori golfer] [sic] Michael Campbell will turn out the better of the two. He’s got more “Maori dog” in him,’ the latest issue of New Zealand Golf quotes the official as saying [DNZE]].
2005		www.kiwiblog.co.nz 26 Aug. [blog] What do you expect from these anti euro thieves, none so cunning as a maori dog, hehe, but this lil doggie got caught.

see under shithouse rat n.

very cunning.

1876		C. Hindley Life and Adventures of a Cheap Jack 185: ‘Handsome Jack,’ who was always reckoned to be as artful as a waggon load of monkeys.
1923		Derby Dly Teleg. 15 Dec. 4/3: He could swerve, and he could be as cunning as a wagon load of monkeys.
1926		Breton & Bevir Adventures of Mrs. May 206: You’re as artful as a wagon load of monkeys.
1930		Yorks Eve Post 14 Mar. 10/4: These hermit rats [...] are very clean and more cunning than a wagon load of monkeys.
1949		I.L. Idriess One Wet Season 247: They’re as cunning as a wagon-load of monkeys, Jack.
1968		G. Slatter Pagan Game (1969) 158: Luckiest player I ever saw, said old Bert. Cunninger than a cartload of monkeys.