Garden tools with long handles and multiple teeth or tines for gathering leaves and smoothing soil; or men known for wild, dissolute behavior and loose morals.
From Old English 'raca' (to scrape or rake). The tool meaning is primary; 'rake' as a roguish man came later, possibly from 'rake-hell' (a man as wild as hell), using 'rake' as an intensifier.
A 'rake' as a bad boy is actually a shortened slang term from 'rake-hell'—a man who lives so wildly he seems to be playing with the devil! This meaning was hugely popular in 1700s literature, where 'rakes' were seductive rogues you weren't supposed to like but secretly found charming.
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