Green’s Dictionary of Slang

1. (orig. US) an armed robbery.

1878		in F. Roe Army Letters from An Officer’s Wife (1909) 206: The driver is their only protector, and the stage route is through miles and miles of wild forest, and in between huge boulders where a ‘hold-up’ could be so easily accomplished.
1885		Harper’s Mag. Apr. 695/2: Darkness [...] into which one ventured with grave apprehensions lest a ‘hold-up’ might be in waiting for him [DA].
1898		Coconino Sun (Flagstaff, AZ) 20 Aug. 5/2: The notorious train robbers (...] were accused of the Grants holdup on the Santa Fe Pacific and the Santa Fe holdup at Belen.
1901		J. Flynt World of Graft 18: Take a walk some night way out on the south side where a lot of hold-ups have come off, and see how many coppers you’ll find.
1917		‘A-No. 1’ From Coast to Coast with Jack London 57: He had personally passed through a number of holdups by hoboes who [...] had relieved him of his six-shooters.
1923		N. Anderson Hobo 23: A holdup has been committed in town the night before and they intend to prevent any more from being committed, ‘So you fellers have to leave’.
1935		D. Lamson We Who Are About to Die 194: The kid had come around and propositioned Mike to stage the hold-up.
1947		Dundee Courier 10 May 2/3: A man who was detained [...] in connection with an alleged armed hold-up.
1949		Monteleone Criminal Sl. (rev. edn).
1954		J. Thompson Swell-Looking Babe 18: I don’t believe there’s ever been a successful hold-up of a major hotel.
1964		Larner & Tefferteller Addict in the Street (1966) 114: They used to give people holdups.
1979		P. Hamill Deadly Piece 149: He was shot in a cheap holdup in Brownsville.
1999		Indep. 26 July 12: Street brawls, drunkeness, bus hold-ups, rapes, robbery.

2. (orig. US, also hold-up artist, hold-up man) an armed robber.

1888		Detroit Free Press 13 Oct. n.p.: Mounted on a white horse, he started on a land-prospecting tour and ran against a party of hold-ups [F&H].
1897		Chieftain (Socorro, NM) 26 Mar. 1/4: A party of four or five rustlers or holdups passed through this country [...] stealing four horses .
1909		W.M. Raine Brand Blotters (1912) 72: How many of the hold-ups were there?
1911		C.E. Mulford Bar-20 Days 143: Why, he’s a two-laigged hold-up! [...] He’s the biggest thief I ever knowed.
1916		J. Lait ‘Charlie the Wolf’ in Beef, Iron and Wine (1917) 33: The police were inquiring after Benny the Bear, a daylight holdup man.
1920		Western Times 2 Nov. 3/1: he desired to rid himself of his wife, and hired a man [...] to play the part of ‘hold-up man’.
1928		M.C. Sharpe Chicago May (1929) 256: The fake hold-up man may beat the gent.
1937		D. Fuchs Low Company 127: I don’t like to do with hold-up men, with gangsters.
1938		Smith’s Wkly (Sydney) 26 Feb. 3/4: Shootings among the ‘hold-up’ artists were banned .
1944		N. Davis Rendezvous with Fear 29: He was a revolutionary, not a bandit or a hold-up man.
1952		Dundee Courier 27 Nov. 2/3: [headline] Woman struck hold-up man.
1960		E. De Roo Big Rumble 117: Papa acted very reserved when the detectives came to question him about the hold-up man.

3. (US) an instance of extortion; lit. or fig.; also attrib.

1910		Sat. Eve. Post 27 Aug. 6/3: Our house [...] cost twenty-five thousand dollars, exclusive of the plumber’s little hold-up and the Oriental rugs [DA].
1914		Bulletin (Sydney) 23 July 26/4: I have since found out that private banks charge 6d. for remitting £25 or under. But 1s. for £5 or under – well, it’s a fair hold-up.
1920		Ade Hand-made Fables 162: The Members of the cruel Hold-Up Gang knew that Ebeneezer was sincere.
1931		W.R. Burnett Silver Eagle 107: Molina [...] counted out seventy-five one thousand dollar bills. ‘ [...] I’ll pay your price providing it ain’t a holdup’.
a.1948		(con. early 1930s) C. McKay Harlem Glory (1990) 22: Most people borrowed money with no intention of paying it back; it was just a respectable holdup.
1952		Lait & Mortimer USA Confidential 15: This does not mean every holdup, heisting or second-story job is acted and voted on by a select committee.