Checkered past
⇨ a personal history that includes both successes and failures, or both ethical and unethical
behavior. The expression is generally used in a negative sense, focusing more on the failures and
unethical behavior than on the successes and behavior.
1. I don’t think Larry is a very good marriage prospect. I’ve heard he has quite a checkered
past.
2. The personnel director of the company refused to consider Mr. Dupont’s application for
employment because of his checkered past.
The expression originates from the alternating black ana white (opposite colors) of a checker
board.
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