Green’s Dictionary of Slang

1. to smuggle, to transport illegally (generally, but not invariably of liquor); thus bootlegging n.

1898		R. Kerlin Camp Life of 3rd Regt. 29: The cases [...] have been less frequent, ‘two-step moonshine’ having been boot-legged into camp.
1904		Commoner (Lincoln, NE) 2 Dec. 5/3: Cherokee Indians are becoming cocaine fiends [...] It is said that the drug is being bootlegged.
1908		‘O. Henry’ ‘The Hand that Riles the World’ in Gentle Grafter (1915) 62: I will [...] guarantee you impunity in boot-legging whiskey for twelve months.
1912		Day Book (Chicago) 27 Mar. 20/2: After having sold considerable whiskey to sporty young bucks [she] was charged with bootlegging.
1924		G. Henderson Keys to Crookdom 280: Adventurers, ex-convicts [...] barkeepers, clerks and even bankers and financiers deserted their old loves for the new – bootlegging.
1935		N.E. Williams His Hi De Highness of Ho De Ho 36: A ‘reefer man’ is a peddler who bootlegs these cigarets.
1937		E. Anderson Thieves Like Us (1999) 20: Up until a year ago, Dee Mobley had been bootlegging corn whisky.
1941		K. Tennant Battlers 237: Cherry-bootlegging had always been one of Orion’s chief entertainments, and fully half as many stolen cases of cherries were shipped away as there were legitimate cases picked.
1952		Lait & Mortimer USA Confidential 122: The cab-drivers who bootleg and pimp.
1955		‘Blackie’ Audett Rap Sheet 51: That’s when I went to bootlegging – running whisky across the line from British Columbia into Idaho and Washington.
1960		Mad mag. Sept. 30: I sure like bootlegging, dope-pushing [and] killing.
1971		B. Moyers Listening to America 176: I had to bootleg it. That’s a sad commentary on bureaucracy.
2000		Indep. 1 Mar. 4: We knew that bootlegging and supplying of smuggled drink was going on.
2021		Breen & Conlon Hitmen 84: Hunt’s bootlegging talents had not gone unnoticed.

2. to manufacture and sell illegal liquor; thus bootlegging n. [later 20C use is SE].

1926		L.C. Wimberly ‘American Political Cant’ in AS II:3 138: The war on liquor gave birth and currency to ‘prohibition,’ ‘bootlegging,’ ‘drys,’ ‘wets,’ ‘bone dry,’ and ‘home brew’.
1931		D. Runyon ‘Tobias the Terrible’ in Runyon on Broadway (1954) 107: She goes around with a guy [...] who runs the Smoke Shop, and bootlegs ginger extract to the boys in his back room.
1946		G. Wilson Fidelity Folks 54: He stoutly maintained that a regulated open saloon was to be preferred to the evils of moonshining and boot-legging [DA].
1952		Lait & Mortimer USA Confidential 19: The organized underworld is unmolested in the things that count, like dope, union rackets, protection, hijacking, counterfeiting, smuggling, blackmail, bootlegging and moonshining.
1978		R. Caron Go-Boy! 124: Later on, when Dad’s bootlegging business boomed, the trips were done for the quiet pleasure of getting away.
1999		‘Master Pimp’ Pimp’s Rap 32: He arrested his own mama for running a whorehouse and bootlegging whiskey.

3. to sell cheaply.

1941

B. Schulberg What Makes Sammy Run? (1992) 9: ‘I got a bargain on two seats right up in front.’ [...] ‘Someone bootlegging in the lobby?’.

4. to make an illegal copy of music, video etc.

1997–2001		Online Sl. Dict. 🌐 boot-leg [...] v 1. to transfer unauthorized material. (‘He boot-legs music on the black market’.).
1999		Guardian Guide 12–18 June 98: Joss Whedon has publicly condoned the pirating, bootlegging and internet distribution.
2007		B. Coleman Check the Technique 62: ‘Nervous put out Diggin’ in Dah Vaults, which was not authorized by the group [...] Nervous went back and bootlegged our shit!’ .