Hmmm... I suppose you should open your log file in game "L" button and read the quest... It's called Mind of..
If you pay attention, each one of the guys have their own specialty, Hermosa (Lady trainer) is better at melee skills, Radcliff, the drunk guy is better at enchanting weapon, and Wesson is better at enchanting armors, and then, later in the game i found some "Wesson's Goods" that maybe could change the duel result... who knows, but then, chose by the focus you want in game, they're not the just to die xD