1570s of armies; from 1882 in field sports; by 1905 in the political sense (compare left wing). Right-winger is attested by 1919 in U.S. politics; 1895 in sports.
to win something hands down (1855) is from horse racing, from a jockey's gesture of letting the reins go loose in an easy victory.
The Two Thousand Guinea Stakes was not the best contested one that it has been our fortune to assist at. ... [T]hey were won by Meteor, with Scott for his rider; who went by the post with his hands down, the easiest of all easy half-lengths. Wiseacre certainly did the best in his power to spoil his position, and Misdeal was at one time a little vexatious. [The Sportsman, report from April 26, 1840]
Ancient Greek had akoniti "without a struggle, easily," from akonitos (adj.), literally "without dust," specifically "without the dust of the arena."