Green’s Dictionary of Slang

1. to commit an armed robbery.

1851		Oquawka (IL) Spectator 5 Feb. 1/7: At St. Louis he held up [...] several men and got more or less money [DA].
1879		Chicago Trib. 9 May 2/2: Later they took a jug of whisky away from a granger, maltreated a yearling colt, and ‘held up’ two men for their money [DA].
1888		Detroit Free Press 8 Dec. n.p.: One man held up six stage passengers in Arizona the other day and robbed them of $2,000 [...] [F&H].
1900		Marvel 21 Dec. 10: Kennel [...] leant sideways in his saddle to peer into the face of the ruffian who was holding him up.
1910		‘Doss Chiderdoss’ ‘The Protean Policeman’ Sporting Times 26 Nov. 1/3: Some ‘nuts’ from Pincher’s Alley, out for trade, / Were just holding up a toff, and clearing his ‘skyrockets’ out.
1928		M.C. Sharpe Chicago May (1929) 22: It was decided to hold up and rob a mail and express-train.
1938		R. Chandler ‘Red Wind’ in Red Wind (1946) 25: Oh! You think you’ll hold me up, I suppose!
1945		Chicago Trib. 27 Dec. 13/4: Edgar Black [...] was shot and killed [...] by police who saw him holding up a man [DA].
1957		Kerouac On The Road (1972) 136: In Chicago he planned to hold up a Turkish bath.
1974		(con. 1960s) R. Price Wanderers 62: Winston Knight and Raymond Firestone held up a sporting goods store last year and took everything.
1981		A. Weller Day of the Dog 154: All I need is someone else to hold it up, because the old codger there knows me.

2. to cheat, to blackmail.

1909		J. Ware Passing Eng. of the Victorian Era 153/2: Hold up (Society, 1860 on). To be cheated or turned to account. From the American highway-man’s habit of calling upon his victim to ‘hold up’ his hands, that he may not fire.
1931		G.F. Willison Here They Dug Gold 86: I was often ‘held up,’ but I never found it profitable to kick about it [DA].
1959		E. De Roo Go, Man, Go! 46: Now here it was—blackmail. No other word for it. Gil, his buddy, holding him up.

3. (US) to demand, esp. to charge an exorbitant price.

1889–90		Barrère & Leland Dict. of Sl., Jargon and Cant.
1899		Ade Fables in Sl. (1902) 177: A Bazaar, the purpose of which was to Hold Up the Public for the Benefit of a Worthy Cause.
1912		J. London Smoke Bellew Pt 10 🌐 He grumbled because the little restaurant across the street had held him up for two dollars and seventy-five cents for a paltry hundred and thirty-four eggs.
1925		R. Lardner ‘A Day with Conrad Green’ in Coll. Short Stories (1941) 165: Fifteen hundred dollars! That’s a joke! Nobody’s going to hold me up!
1940		J.H. O’Hara Pal Joey 4: I didn’t hold them up for too much of the ready.
1967		P. Thomas Down These Mean Streets (1970) 39: I looked at the roller skates, and I felt a little bad about how I had held Poppa up for them.