Baldwin

Middle English bold, from Old English beald (West Saxon), bald (Anglian) "stout-hearted, brave, confident, strong," from Proto-Germanic *balthaz (source also of Old High German bald "bold, swift," in names such as Archibald, Leopold, Theobald; Gothic balþei "boldness;" Old Norse ballr "frightful, dangerous"), perhaps (Watkins) from PIE *bhol-to-, suffixed form of root *bhel- (2) "to blow, swell."

The meaning "requiring or exhibiting courage" is from mid-13c. Also in a bad sense, "audacious, presumptuous, overstepping usual bounds" (c. 1200). From 1670s as "standing out to view, striking the eye." Of flavors (coffee, etc.) from 1829.

The noun meaning "those who are bold" is from c. 1300 in both admiring and disparaging senses. Old French and Provençal baut "bold," Italian baldo "bold, daring, fearless" are Germanic loan-words. Related: Boldly; boldness.

"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.