Idiom meaning, usage examples, facts

1. Larry has quite a checkered past, but things are getting better. He has a new job and is saving for a new apartment.
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 and white (opposite colors) of a checker board. It is generally used in a negative sense, focusing more on failures and unethical behavior than on successes and ethical behavior.