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1620s, "a sentinel," agent noun from round (n.) on notion of "one who makes the rounds." Sense of "chronic drunkard or criminal" is from 1854, on notion of one who is habitually in and out of jails or bars. Rounders, a baseball-like game, attested from 1828.
A debauchee; habitual carouser: some rich ''rounders'' of the town
[1854+; one who ''makes the rounds'' of saloons]
old English game that never became a seriously competitive sport, although it is probably an ancestor of baseball. The earliest reference to rounders was made in A Little Pretty Pocket-Book (1744), in which a woodcut also showed the children's sport of baseball. The Boy's Own Book (2nd edition, 1828) devoted a chapter to rounders. In 1889 the National Rounders Association of Liverpool and the Scottish Rounders Association were formed. A National Rounders Association was founded in 1943.