Green’s Dictionary of Slang

1. (orig. US) short of money; thus shyness, reluctance to honour a bet.

1819		P. Egan Key to the Picture of the Fancy going to a Fight 9: Very little [betting] is done upon tick, as staking is now the most preferable and decisive mode of betting [and] prevents shyness upon either side.
1821		D. Haggart Autobiog. 39: Although I had not been idle during these three months, I found my blunt getting shy.
1824		N.-Y. Eve. Post 23 July 2/2: There were but few bets made, from a general impression that all was not right, and the knowing ones reaped but a slender harvest — all were shy.
1897		E.W. Townsend Chimmie Fadden 74: We’re shy on our ante yet.
1901		A. Binstead More Gal’s Gossip 83: One good reason why I did not back it was that I was somewhat ‘shy of the Ready John’.
1907		B. Fisher A. Mutt in Blackbeard Compilation (1977) 11: And while he is a trifle shy in the bank roll, he is wealthy in experience.
1913		H.G. Van Campen ‘Life on Broadway’ in McClure’s Mag. Mar. 40/2: I know nothin’ of her habits, ’ceptin’ that the day she left the drawer was eighty cents shy, an’ I was nicked for it.
1923		H.C. Witwer Fighting Blood 59: Mrs Willcox’s a hundred dollars shy on a note held by the bank and due in a week.
1939		‘Flann O’Brien’ I Knock at the Door 196: Only ninepence in it, so there’s a wing missin’ – who’s shy?
1968		D. O’Grady A Bottle of Sandwiches 25: We’re a bit shy on the necessary, an’ we’re lookin’ for work.

2. of anything other than money, lacking in amount or quality.

1825		Pierce Egan’s Life in London 9 Jan. 397/3: The attendance of the amateurs, on Tuesday last, at Gipsy Cooper's Benefit, was rather shy .
1889		World (N.Y.) 9 Aug. 3/1: Just here it was discovered that they were ‘shy’ on both uniforms and bats.
1899		E. Townshend ‘Chimmie Fadden Recognises...Some Old Friends’ 5 Feb. [synd. col.] De foist thing we seen was a loidy what had only a head, and she was shy on everyting below her chin.
1905		H. Green Actors’ Boarding House 355: A little shy on regular feeds himself, but Kid hadn’t missed one.
1915		R. Lardner ‘Alibi Ike’ in Coll. Short Stories (1941) 38: Somebody organized a little game o’ cards. They was shy two men to make six and ast I and Carey to play.
1916		B.M. Bower Phantom Herd 80: Go and order the cavalry costumes, Beckitt; and say! You tell them down there if they’re shy on the number, they better set down and make enough.
1917		R. Lardner ‘The Facts’ in Coll. Short Stories (1941) 458: He was fourteen highballs shy of comedy.
1927		D. Hammett ‘The Big Knockover’ Story Omnibus (1966) 288: It was a little shy of two in the morning when I turned back into Market Street.
1948		Democrat 1 Apr. 1/1: Gould’s gobbler [...] had a beard which was just a bit shy of 12 inches.
1996		(con. 1949) G. Pelecanos Big Blowdown (1999) 164: I’m a little shy of the drinking age.