"small two-masted ship," 1520s, from French brigandin (15c.), from Italian brigantino, perhaps "skirmishing vessel, pirate ship," from brigante "skirmisher, pirate, brigand" from brigare "to fight" (see brigade and compare brigand).
subdivision of an army, 1630s, from French brigade "body of soldiers" (14c.), from Italian brigata "troop, crowd, gang," from brigare "to brawl, fight," from briga "strife, quarrel," perhaps of Celtic (compare Gaelic brigh, Welsh bri "power"), from PIE root *gwere- (1) "heavy." Or perhaps from Germanic.
c. 1400, also brigaunt, "lightly armed irregular foot-soldier," from Old French brigand (14c.), from Italian brigante "trooper, skirmisher, foot soldier," from brigare "to brawl, fight" (see brigade). Sense of "robber, freebooter, one who lives by pillaging" is earlier in English (late 14c.), reflecting the lack of distinction between professional mercenary armies and armed, organized criminals.
Probably then it was in the sense of skirmishers that the name of brigand was given to certain light-armed foot-soldiers, frequently mentioned by Froissart and his contemporaries. ... The passage from the sense of a light-armed soldier to that of a man pillaging on his own account, is easily understood. [Hensleigh Wedgwood, "A Dictionary of English Etymology," 1859]