What does the phrase “He has a chip on his shoulder” mean?

When someone says “he has a chip on his shoulder” it means that the person being talked about is holding on to something negative – like a grudge or some form of jealousy – in his or her mind. The phrase “he has a chip on his shoulder” is meant to create an image that the person is holding on to something – like he is carrying an extra load on his shoulders, and that extra load is really something that’s mental and negative.

Example of “He has a chip on his shoulder” in a sentence:

"Because Joseph grew up very poor, and always 
disliked rich people, he has a chip on his shoulder
whenever he meets someone who is wealthy.

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