I'm talking about guys whose role was to fight. They did it regularly and regularly lost. Keith Magnuson who played for the Chicago Blackhawks from 1969-1980 gets my vote. Every off season he'd take some kind of lessons (boxing, karate, judo, etc.) or fitness program to improve his fighting ability, and continue to get whupped. He was a very gritty and willing combatant that could never seem to win a fight.