Green’s Dictionary of Slang

(US black) drinking one’s way through a variety of liquors, in ascending order of price.

1941

D. Burley N.Y. Amsterdam Star-News 5 July 13: Ladder Drinking means starting out with a beer [...] then drinking your way up the scale [...] to champagne.

(US) to be (reasonably) intelligent; thus couldnt see a hole in a ladder, to be stupid.

1915		T.A. Dorgan Indoor Sports 25 Feb. [synd. cartoon] I couldn’t get away with stuff on my wife. She’s too wise. She can see a hole in a ladder, believe me.
1915		T.A. Dorgan Indoor Sports 3 July [synd. cartoon] He couldn’t see an ad writer before; he couldn’t see a hole in a ladder.

1. to be hanged.

1607		G. Wilkins Miseries of an Enforced Marriage Act IV: I would not go up the ladder twice for anything.
1672		M. Atkins Cataplus 7: Many a thief and high-way padder / Mounted up on fatal Ladder.
1726		A. Smith Memoirs of... Jonathan Wild 21: Where little, petty, scoundrel Rogues depart / The World upon a Ladder, or a Cart.
1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue n.p.: You will go up a ladder to bed, i.e. you will be hanged. In many country places, persons hanged are made to mount a ladder, which is afterwards turned round or taken way, whence the term ‘turned off’.
1811		Lex. Balatronicum n.p.: Go up the ladder to rest; to be hanged.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue [as cit. 1811].
1831		Quizzical Gaz. 27 Aug. 8/2: My poor father [...] mounted a ladder , and never walked down again.
1892		Oakleigh Leader (Nth Brighton, Vic.) 3 Sept. 45/5: Thieves [...] don’t like to hear of a man being hanged. He goes for a ‘hearty choke with caper sauce’ or he ‘goes up the laddder to bed’ or he ‘dies in a horse’s nightcap, i.e. a halter.

2. (UK und. ) to be condemned to the treadmill.

1838

‘Paul Pry’ Oddities of London Life II 285: [V]ich is easiest, picking oakum, or going up the ladder? (working with his feet as if on the treadwheel).