Green’s Dictionary of Slang

1. (also chigger) a clandestine, illicit still.

a.1790		H.T. Potter New Dict. Cant (1795).
1809		G. Andrewes Dict. Sl. and Cant.
1823		‘Jon Bee’ Dict. of the Turf, the Ring, the Chase, etc. 49: Chigger — a still, ‘Working the chigger or jigger;’ a private still.
1824		Compl. Hist. Murder Mr Weare 241: Probert and these two persons were in the jigger at Gill’s-hill; and it was a most successful business.
1835		G. Kent Modern Flash Dict.
1848		Flash Dict. in Sinks of London Laid Open.
c.1850		Duncombe New and Improved Flash Dict.
1864		in B.L. Ridley Battles and Sketches of the Army of Tennessee (1906) 444: It was not considered shocking to [...] partake of the hospitality of a soldier’s tent, in the shape of a ‘jigger’.
1873		Sl. Dict.

2. (UK Und., also jigger man) one who operates an illicit still and sells the liquor; also attrib.

1831		Northampton Mercury 17 Sept. 2/1: Resurrection of a Gin-Spinner [...] They discovered a private distillery, and apprehended a known ‘jigger man,’ a private still worker, named Dennis Duggan. [...] About six months ago [...] a gin-spinning establishment which he had formed [...] was broken up by the same officers.
1856		H. Mayhew Great World of London I 46: ‘Jiggers’ (defrauding the excise by working illicit stills).
1861		(con. 1840s–50s) H. Mayhew London Labour and London Poor I 378/2: It is suspected that he likewise does a little in the ‘jigger line’ [...] the packmen are suspected of trafficking.

3. bootleg liquor; also attrib.

1853		Diogenes ii 199: Jigger-gin will kill body and brain faster than arrack punch or Sangaree [F&H].
1861		(con. 1840s–50s) H. Mayhew London Labour and London Poor I 387/1: The jigger spirit is above proof, and a pint will make two pints of gin-palace stuff.

4. a drink of spirits, a dram; also attrib. [SE in 20C+].

1857		Harper’s Mag. Mar. 443/1: Betsy [...] would drink numerous consecutive jiggers of raw whisky without winking [DA].
1881		Butte (MT) Daily Miner 14 Apr. 1/3: ‘Blizzard’ [...] There has been extensive use of the word in Pennsylvania for many years [...] A drink of any intoxicant, generally applied to whisky. Synonymous with the slang ‘a slug,’ ‘a smile,’ ‘a jigger,’ ‘a bumper.’ Example: ‘Let’s take a blizzard.’.
1891		Salina Dly Republican (KS) 25 Sept. 3/2: Jigger — Any sized drink of any kind of whiskey.
1892		A.E. Lee Hist. Columbus I 335: The ‘jigger’ was a dram of less than a gill [DA].
1920		Ade Hand-made Fables 149: The Colonel’s Birthday Parties had gone the way of the Jigger and the Jazz Band.
1938		G.G. Korson Minstrels of the Mine Patch 315: Jigger Boss: A company official who dispersed whiskey rations at Maunch Chunk in the 1820’s.
1942		J. Mitchell ‘Professor Sea Gull’ in Joe Gould’s Secret (1996) 21: A couple of beers or a single jigger of gin will untie his tongue.
1956		I. Fleming Diamonds Are Forever (1958) 91: People are so dam’ sensitive about colour around here that you can’t even ask a barman for a jigger of rum. You have to ask for a jegro.

5. a small glass or metal cup, a measure used in mixing cocktails.

1917		O.O. McIntyre New York Day by Day 16 Nov. [synd. col.] The ‘jigger’ glass which many saloon-keepers are intriducing to guarantee that no patron [...] can get over the two and one-half finger mark.
1927		H. Asbury Gangs of N.Y. 93: Standing before the bar drinking a jigger of hot rum.
1946		K. Fearing Big Clock (2002) 94: He dropped the first jigger [...] and only finally managed to fill the second one.
1947		B. Schulberg Harder They Fall (1971) 105: He held up his jigger ceremoniously.

6. (US) a young man who frequents soda fountains in the hope of picking up girls.

1922

L.A. Times 4 May II 4: Herewith another installment of snappy younger generation slang just broadcast from eastern points, where it has its origin: [...] Jigger: A soda-fountain Adonis.