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This has gotten lost in all the false meanings. A chip on his shoulder comes from the days when there was a [formal declaration] for a fight, punch-up etc. When a person disagreed strongly with someone over a personal belief, they would place a chip of wood on their shoulder and dare the other to [knock it off]. Once the other person did this signaled the beginning of the fight and thus punches were thrown. Examples of this can be seen in old British movies circa 1930-1950's. We use this idiom to say that someone has a deeply held feeling or [conviction] about something (whether it annoys them or that they won't listen to any other opinion about it) and thus if you disagree then they will vehemently challenge you.
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