According to urban dictionary online, 'checkered past' means "bad history of someone due to unreputable actions from the previous years."

Does it mean the person has a checkered  past because he committed a crime before or not necessarily?

Can it be used in a positive way? Could you please give me some examples of it?

Many thanks.

Original Post


As the Urban Dictionary says, the person has a history of unreputable actions.  Not just one action, but actions plural.  They might not have been crimes per se; they may have been acts of dishonesty or betrayal that were unethical but still within the law.

The point is that because of his checkered past, you should take extra care when deciding whether or not to trust him.  I can't imagine any way that this term could be used to mean something positive about a person.


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