Tom Hennesy(1923-2011)

In the movie "Big Jake" Tom fights John Wayne and Wayne loses. It was the first time in Wayne's long career that he lost a fight. Unless you care to count "The Life of Jimmy Dolan" (1933) in which offscreen he is beaten badly in the ring by Sammy Stein or "Pittsburgh" (1942) in which Randolph Scott prevails in what might be considered a return bout with Wayne who prevailed in "The Spoilers" (also 1942).