"money bet by those in the know," 1926, from smart (adj.). The same phrase earlier meant "money paid to sailors, soldiers, workers, etc., who have been disabled while on the job" (1690s), from a noun derivative of smart (v.) "be painful, hurt." Also "money paid to obtain the discharge of a recruit" (1760), hence "money paid to escape some unpleasant situation" (1818). Sometimes in legal use, "damages in excess of injury done."
"payment of money, cash down," 1570s, old slang, from the title in the Anglican prayer-book of the psalm appointed for Matins on the 25th of the month; it was consequently associated especially with March 25, the new year of the old calendar and a quarter day, when payments and debts came due and money changed hands generally. The title is from the first two words of the fifth division of Psalm cxix: Legem pone mihi, Domine, viam justificationum tuarum "Teach me, O Lord, the way of thy statutes."
1860s, "a good deal, a large amount;" by 1878 in financial speculation, originally in California publications; see deal (n.1). As an ironic expression, popular in American English from c. 1965, perhaps a translated Yiddishism (such as a groyser kunst).
also long-shot, in the figurative sense of "something unlikely," 1867, from long (adj.) + shot (n.). The notion is of a shot at a target from a great distance, thus difficult to make. The phrase by a long shot "by a considerable amount," frequently negative, is attested by 1830, American English colloquial. The cinematic sense of the noun phrase is from 1922. As an adjective by 1975.
1893, American English, in the figurative sense "fear or doubt that reverses an intention to do something;" the presumed Italian original (avegh minga frecc i pee) is a Lombard proverb meaning "to have no money," but some of the earliest English usages refer to gamblers, so a connection is possible.
by 1970, of unknown origin; perhaps arbitrary (see cloud nine). Among the guesses that have been made without real evidence: concrete mixer trucks were said to have dispensed in this amount. Or the yard might be the word used in the slang sense of "one hundred dollars." Several similar phrases meaning "everything" arose in the 1940s (whole ball of wax, which is likewise of obscure origin, whole schmear); older examples include whole hog (see hog (n.)) and whole shooting match (1896); whole shebang (1895).