Green’s Dictionary of Slang

1. (US, also V-spot) a five-dollar bill.

1837		N.Y. Herald 9 May 2/3: V’s, X’s, L’s, and C’s of the Dry Dock Bank.
1840		N.Y. Herald 7 Feb. 2/2–3: When they can raise a cool X. they drive as far as Bradshaw’s, and dine. When they can only circumvent a V., they stop at the Red House, or at the Widow’s.
1848		J.R. Lowell Biglow Papers (1880) 129/2: Gloss. V spot, a five-dollar bill.
1852		C.A. Bristed Upper Ten Thousand 239: He strutted off with his V., to the great amusement of the bystanders.
c.1865		‘Bobbing around!’ in Fred Shaw’s Champion Comic Melodist 20: Be so kind as to lend me a V.
1867		‘Johnny Cross’ ‘When I Felt Awful Blue’ in Orig. Pontoon Songster 18: If a friend asks you to lend a V, it puts you in a stew.
1879		Nat. Police Gaz. (NY) 15 Nov. 14/4: It [...] made all the others more than willing to pass over the Vs.
1897		N.Y. Tribune 16 May 38/2: By the way, Dick, dear old fellow, let me have a V?
1901		‘Hugh McHugh’ Down the Line 21: I took my lonely V and went out into the Promised Land after the nuggets Maddy had put me wise to.
1912		Ade Knocking the Neighbors 229: [He] gave Albert a V and told him to hunt up some of his Boy Friends and take them to a Matinee at the Orpheum.
1928		M. Bodenheim Georgie May 21: They were right on deck for their V’s and ten-spots.
1931		Irwin Amer. Tramp and Und. Sl. 193: V. – Five dollars; a five-dollar bill.
1950		Goldin et al. DAUL 233/1: V. 1. A five-dollar bill.
1962		Ragen & Finston World’s Toughest Prison 822: V – Five dollars.

2. (US prison) a five-year jail sentence.

1931		‘Experience’ in Lingenfelter et al. Songs of the Amer. West (1968) 324: The beak handed me a hard labor ‘V.’.
1950		Goldin et al. DAUL 233/1: V. [...] 2. A five-year sentence.
1965		B. Jackson Get Your Ass in the Water (1974) 132: They sent me up the river to do a little ‘V’ [five-year sentence].