Green’s Dictionary of Slang

1. bright, alert, aware.

1718		C. Hitchin Conduct of Receivers and Thief-Takers 20: The Cull is leery, alias the Man is shy.
c.1786		Grose Classical Dict. of the Vulgar Tongue ms. additions n.p.: Leary flash Mot — A knowing Cyprian.
c.1811		‘A Leary Mot’ in Farmer Musa Pedestris (1896) 77: Rum old Mog was a leary flash mot.
1822		Tom And Jerry; Musical Extravaganza I v: We must be on the leery.
1824		Morn. Chron. (London) 21 Apr. 4/3: The leary ones rose with the lark and the road towards Hounslow exhibited the usual signs of ‘Summat a going on’.
1829		‘On the Prigging Lay’ trans. of ‘Un jour à la Croix Rouge’ in Vidocq (1829) IV 263: Are they out and outers, deary? / Are they fogle-hunters, or cracksmen leary?
1835		‘The Spring Bedstead’ in Knowing Chaunter 17: So, says my leary mot, / I’ll go and have a flare-up! / So to a crib we sped, / To do as she requested.
1836		‘The Bastard’s Christening’ in Comic Songster and Gentleman’s Private Cabinet 12: There vos bow-legged Bet, and randy Sal, / Leery Suke, who had never been scragg’d.
1845		J. Lindridge Sixteen-String Jack 124: The dashy, splashy, leary little stringer, / Mounted his roan, and took the — Phililoo! [...] And leary-eyed Poll and blue-eyed Moll.
1848		Bell’s Life in Sydney 18 Nov. 2/4: The Snob came up lively as a kitten, and leary as a land-sbark.
1854		G.J. Whyte-Melville General Bounce (1891) 343: The very detectives would sneer to learn that ‘Leary Tom’ and ‘the Battersea Big ’un’ had been frightened at their own shadows.
1861		Melbourne Punch ‘The Lay of the Lags’ 14 Mar. 1/1: For the leary bloakes in office, / Mean to nick the Peelers’ pay.
1865		Leaves from Diary of Celebrated Burglar 70/1: That the-irs tu ‘leery’ a ‘moll’ fur any ’un to ‘dip’.
1879		‘’Arry on the ’Igher Education of Women’ in Punch 5 Apr. in P. Marks (2006) 151: The thing to do with a kid is to bring him up leary and smart.
1881		Bulletin (Sydney) 8 Jan. 8/3: With expression ‘fly’ and ‘leary,’ / With as much as he can carry / Of bad beer and rum, come ’Arry / In a ‘rig’ that’s quite the ‘cheese.’.
1891		Exeter & Plymouth Gaz. 15 Oct. 3/6: He clearly is a ‘leary bloke’.
1896		Regiment 9 May 91/2: Tho’ not practical, still I am leery .
1895		C. Crowe Aus. Sl. Dict. 44: Leery, wide-awake; look out.
1908		‘O. Henry’ ‘The Man Higher Up’ in Gentle Grafter (1915) 148: Eat, drink and be leary.
1953		S. Bellow Augie March (1996) 17: A big, fresh, leery-looking woman.
1962		B. McGhee Cut and Run (1963) 55: She was certainly a ‘leery’ customer. Knew more ways of making money than the fellow who wrote that book.
2015		‘Elvis Costello’ Unfaithful Music 221: Steve Jones and Paul Cook from the [Sex] Pistols [...] were just two leery lads who, in another life, might have been nicking lead off a church roof, and I mean that in a complimentary way.

2. guarded, suspicious of or uneasy about someone or something.

1718		C. Hitchin Regulator 20: The Cull is leery, alias the Man is shy.
1796		Grose Classical Dict. of the Vulgar Tongue (3rd edn) n.p.: Leery. On one’s guard.
1796		Sporting Mag. Aug. VIII 253/1: If you are in the least leary, you must go strait forward to reform.
c.1800		‘Tom the Drover’ No. 30 Papers of Francis Place (1819) n.p.: Her Cull being leery he bon’d her before she got out of the room.
1811		Lex. Balatronicum [as cit. 1796 Grose].
1821		Egan Life in London (1869) 172: ‘The sooner you paint me a picture,’ said the leary Bum-trap, ‘the sooner the door will be open to you’.
c.1830		‘Smith’s Frolic’ in Holloway & Black (1979) II 61: The mot she seem’d leary and gave me a frown.
1842		Whip & Satirist of NY & Brooklyn (NY) 8 Jan. n.p.: Arthur, however, was too leary [...] and got away.
1848		Ladies’ Repository (N.Y.) Oct. VIII:37 316/2: Leary, shy; suspicious; doubtful.
1859		Hotten Dict. of Modern Sl. etc. 58: LEARY [...] shy.
1861		(con. 1840s–50s) H. Mayhew London Labour and London Poor I 278/2: When leary Joe Scott, / Dealt in ‘Donovan’s hot’.
1867		Nat. Police Gaz. (NY) 21 Sept. n.p.: Owing to the [...] presence of a ‘fly-cop’ business outside was duff, although a ‘mob’ of city ‘mokes’ were on the lookout for ‘swag’ but were very ‘leery’.
1877		Five Years’ Penal Servitude 146: A ‘leary look,’ in which fear, defiance and cunning are mixed up together.
1881		Newcastle Courant 16 Sept. 6/5: Vardo, the grabs are leerie, don’t wait for darkmans but melt.
1887		Grantham Jrnl 18 June 7/1: It’s all tommy rot about the Duchess of Dilwater not being on speaking terms with her leary old bloke of a spouse.
1888		J. Runciman Chequers 85: The bastard gipsy smiled in a ‘leary’ fashion.
1892		W. Norr Stories of Chinatown 50: Pete Reagan and Kid Carroll had turned off some big nabob, and getting leary, had given me the stuff to keep until the thing blew over.
1901		J. Flynt World of Graft 100: I got so leary ’cause I couldn’t understand what the people about me was sayin’ that I thought they was talkin’ about me all the while, an’ I’d go miles out o’ my way, thinkin’ they was pipin’ me off.
1906		A.H. Lewis Confessions of a Detective 206: All, mind you, just because these joskins [...] gets leery at the noise of the gun.
1917		‘A-No. 1’ From Coast to Coast with Jack London 100: What we were told not only made us even more ‘leary’ of our man, but also instilled us with a yearning to have a squint at the notorious hobo snatcher.
1917		F. Packard Adventures of Jimmie Dale (1918) I x: This Gray Seal dope listens good, Whitey; but, coming from you, I’m leery.
1921		P. & T. Casey Gay-cat 65: Yorky’s all right [...] Don’t be leary about shooting your mouth off before him.
1926		J. Black You Can’t Win (2000) 61: Come on down, kid. Don’t be leery. We’re only a couple of harmless bindle stiffs.
1932		(con. 1910s) J.T. Farrell Young Lonigan in Studs Lonigan (1936) 29: He felt a little leary about leaving it all behind.
1936		Archie Seale Man About Harlem 29 Aug. [synd. col.] Not that Harlem was short of money to bet on Joe Louis [...] they were just leery.
1937		J. Curtis There Ain’t No Justice 44: I seen her walking along the Avenue to-night with a leary looking geezer.
1943		Baker ‘Influence of American Sl. on Australia’ in AS XVIII:4 255: Leary means suspicious or inferior in the U.S.; we have changed the pronunciation to lairy and it means flashy, especially flashily dressed.
1947		F. Brown Fabulous Clipjoint (1949) 77: Damn if I’m not a little leary of you myself.
1947		S. Lewis Kingsblood Royal (2001) 135: They make us awful leery of our dear white friends.
1951		M. Spillane One Lonely Night 73: Even a general had to be leery of the MVD.
1953		K. Tennant Joyful Condemned 20: I’d be more leary of the brush if I was you.
1958		A. King Mine Enemy Grows Older (1959) 47: I am instinctively leery of joining anything.
1960		C. Cooper Jr Scene (1996) 11: I wouldn’t bust you, if that’s what you’re leery about.
1968		S. Gore Holy Smoke 82: I’ll be a bit leary of ’em, just the same.
1974		G.F. Newman You Flash Bastard 275: I’ve always been a little leary of you in the past, figuring you as one very treacherous detective.
1977		(con. 1960s) D. Goines Black Gangster (1991) 59: Ain’t you kind of leery of those white kids.
1984		C. White Life and Times of Little Richard 151: Richard was also very leery of people being up and around in his room during the daytime.
1990		(con. 1930s–60s) H. Huncke Guilty of Everything (1998) 250: At that time Jack would smoke a little pot, but he was leery of the needle.
1998		G. Burn Happy Like Murderers 55: Caroline was nervous. She was still a bit leery.
1999		G. Seal Lingo 38: Other convict terms that are either still with us or have only relatively recently dropped include: [...] leary (leading to lair).
2000		Guardian Guide 1-6 Jan. 11: When I first got the script I was a little leery about doing it.
2004		T. Winton ‘Long, Clear View’ in Turning (2005) 199: He’s leery of the dog.
2010		Codella and Bennett Alphaville (2011) 290: Obviously leery of being fucked with by a non-Puerto Rican cop.

3. cunning, underhand.

1833		H. Smith Gale Middleton 1 158: Damn the leary cove! the wind isn’t out of him yet. Twig him another crack, Jem!
1842		Cornwall Chron. (Launceston, Tas.) 22 Oct. 2/7: The following is a sample of the polite language, of the Xaminer (Oct. 19) [...] The Doctor did not see his game, but knowing that he had a leary cove to deal with, was wary.
1866		Sportsman 27 Sept. 2/1: Notes on News [...] The Court condemned that ‘leery’ gentleman-coper to take the horse back, refund the price, pay the expense of standing at livery, and pay the cost of the suit.
1891		Exeter & Plymouth Gaz. 15 Oct. 6/4: He always draws near any bargaining country people, and, with an insinutating manner mixes himself up with it. He clearly is a ‘leary bloke’.
1900		J. Conrad Lord Jim 241: The poor man, some time or other, had been heard to express the intention of winning Captain Brown to a better way of life... ‘Bag Gentleman Brown for Glory’ – as a leery-eyed loafer expressed it once.
1916		C.J. Dennis ‘Introduction’ in Moods of Ginger Mick x: An’ that is orl there wus to Mick, wiv orl ’is leery ways.
1939		R. Chandler Big Sleep 164: It’s a leery job — buckin’ guys like Eddie Mars.
1958		(con. 1940s) B. Behan Borstal Boy 20: You London blokes are so leery.
1966		T. Keyes All Night Stand 45: The leery bastard.
2018		G. Gilmore Base Nature [ebook] A crowd of men approaches her with leery smiles.

4. (US) hungover, drunk.

1891		J. Maitland Amer. Dict. Sl.
1915		M.G. Hayden ‘Terms Of Disparagement’ in DN IV:iii 215: leary, leery, drunk.
1933		‘William Juniper’ True Drunkard’s Delight 226: Our tippler may further be [...] leary. [note] American slang gives us leary with the neary.

5. bad-tempered, disagreeable, cheeky.

1903		A.H. Lewis Boss 178: It was my name made him leary.
1910		Bulletin (Sydney) 8 Sept. 10/1: leery liz: ’E’s a shameless cyow, that Judkins! Why, ’e even ’ad the ’ide to stare at me an’ ’Arry when all the pleecemens wuz turnin’ their ’eads away.
1924		C.J. Dennis ‘Introduction’ in Rose of Spadgers 14: The big, softhearted boy ’e’d alwiz been / Be’ind ’is leery ways an’ fightin’ jor.
1937		J. Curtis You’re in the Racket, Too 56: Not what you’d call rough exactly, but on the leery side perhaps.
1958		(con. 1940s) B. Behan Borstal Boy 123: Throwing a can of porridge at a screw that got leery with him.
1977		D. Powis Signs of Crime 191: Leery Bad tempered, disagreeable or cheeky.
1989		T. Blacker Fixx 308: He got well leery when I spent the night with John.
1997		N. Barlay Curvy Lovebox 87: It’s mayhem with leery van drivers everywhere.
2000		J.J. Connolly Layer Cake 31: He’s a leery, bullying cunt is James at times.

6. frightened, hesitant.

1913		J. London Valley of the Moon (1914) 356: Brave as lions when it comes to pullin’ miserable, broken-spirited bindle stiffs, but as leery as a yellow dog when you face a man.
2004		T. Winton ‘Family’ in Turning (2005) 172: He was leery of sharks.

7. (US Und.) of goods, damaged.

1931

Irwin Amer. Tramp and Und. Sl. 119: Leary. – Damaged goods or inferior merchandise; especially that which is peddled by pitchmen, and which is likely to cause trouble for the seller when the purchasers see that what they have bought is not up to standard.

8. (UK black) suspicious.

2017

hubpages.com ‘Roadman Slang 10 Jan. 🌐 Leary - suspicious (totally moves away from the real meaning of the word). e.g. ‘my parents are getting bare leary, I keep coming in at 4am man’.

9. see lairy adj. (2)