1894 Brewer’s / C / Chap
A man, properly a merchant. A chap-man is a merchantman or tradesman. “If you want to buy, Iʹm your chap.” A good chap-man or chap became in time a good fellow. Hence, A good sort of chap, A clever chap, etc. (Anglo-Saxon, ceap-mann.)
⁂ An awkward customer is an analogous phrase.
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Entry taken from Dictionary of Phrase and Fable, edited by the Rev. E. Cobham Brewer, LL.D. and revised in 1895.