Green’s Dictionary of Slang

1. (orig. US) a smuggler or manufacturer of illicit liquor; thus bootlegger turn, a handbrake turn (performed to avoid an on-coming car full of revenue officers or police); also one who sells legal liquor at higher prices, taking advantage of other stores being shut (see cite 1969).

1889		Sanger Rep. in J.B. Thoburn A Standard Hist. of Oklahoma (1916) I. 223: Liquor dealers (or as they are called here ‘boot-leggers’) [DA].
1895		Social Economist 8 159: The ‘bootlegger’ was also another means of avoiding the law. This creature carried bottles of whiskey on his person, which he sold at so much a drink, or delivered to regular customers.
1905		J.W. Carr ‘Words from Northwest Arkansas’ in DN III:i 71: bootlegger, n. An illicit vendor of intoxicating drinks carried on his own person. ‘The officers were down on the railroad looking for bootleggers a few days ago.’.
1910		Bulletin (Sydney) 13 Oct. 19/3: I’ve often wondered what the Americans mean when they speak of ‘boot-leggers,’ ‘pocket-peddlers,’ ‘blind tigers,’ ‘speak-easys’ and ‘blind pigs’ in connection with the ‘dry’ territories in the land of the grilled nigger. I know, of course, that they are all contrivances for the illicit sale of grog [...].
1912		Gurthrie Dly Leader (OK) 13 Sept. 6/4: [headline] Police Landed Another Bootlegger Last Night.
1929		W.R. Burnett Little Caesar (1932) 246: The Monroe gang decided it would be more lucrative [...] to confine their hijacking to smaller bootleggers.
1931		D. Runyon ‘Romance in the Roaring Forties’ in Runyon on Broadway (1954) 33: He is not a bootlegger.
1939		R. Chandler Big Sleep 16: An ex-bootlegger, who went in the trade by the name of Rusty Regan.
1953		L. Uris Battle Cry (1964) 331: After he got a bootlegger he asked me for five pounds.
1969		U. Hannerz Soulside 24: Today’s bootleggers in the area do not make their own liquor but buy it at a discount and sell it at higher prices—something like 25 per cent higher than regular store prices.
1971		R.D. Pharr S.R.O. (1998) 71: Joe Ash, the Logan’s shylocking bootlegger.
1987		T. Wolfe Bonfire of the Vanities 235: He works for a goddamned bootlegger!
2000		Guardian Rev. 1 Jan. 12: There were bootleggers blazing away at each other.
2017		M. Forsyth Short History of Drunkenness 177: Captain John MacArthur [...] was a dishonest, scheming soldier-bootlegger.

2. (US und.) a doctor who performs illegal services, e.g. writing narcotics prescriptions, performing abortions.

1965

H. Williamson Hustler 125: [T]here’s a doctor there. Now this guy got a legitimate office but he’s a bootlegger on the side. If a woman goin’ to have a baby and don’t want to have it, call him. He was givin’ girls drugs too that was dope fiends.

3. (N.Z. prison) officer in charge of the prison drugs dog.

2001

D. Looser Boobslang [U. Canterbury D.Phil. thesis] 27/2: bootlegger n. the police officer in charge of the narcotics detection dog.