wont adj.

"be victorious," c. 1300 fusion of Old English winnan "to labor, toil, struggle for, work at, strive, fight," and gewinnan "to gain or succeed by struggling, conquer, obtain," both from Proto-Germanic *wennanan "to seek to gain" (source also of Old Saxon winnan, Old Norse vinna, Old Frisian winna, Dutch winnen "to gain, win," Danish vinde "to win," Old High German winnan "to strive, struggle, fight," German gewinnen "to gain, win," Gothic gawinnen "to suffer, toil"), from PIE root *wen- (1) "to desire, strive for."

Related: Won; winning. Meaning "gain the affection or esteem of" is from c. 1600. Breadwinner preserves the sense of "toil" in Old English winnan. Phrase you can't win them all (1954) first attested in Raymond Chandler. Winningest is attested by 1804.

"train (an infant or animal) to forego suckling," c. 1200, from Old English wenian "to accustom, habituate," from Proto-Germanic *wanjan (source also of Old Norse venja, Dutch wennen, Old High German giwennan, German gewöhnen "to accustom"), from PIE *won-eyo-, causative form of root *wen- (1) "to desire, strive for."

The sense of "accustom a child to not suckling from the breast" in Old English generally was expressed by gewenian or awenian, which has a sense of "unaccustom" (compare German abgewöhnen, entwöhnen "to wean," literally "to unaccustom"). The modern word might be one of these with the prefix worn off, or it might be wenian in a specialized sense of "accustom to a new diet." Figurative extension to any pursuit or habit is from 1520s.