Checkered past

The phrase "checkered past" typically refers to a person's history or background that is marked by a series of both positive and negative experiences or actions. It connotes a varied and often controversial or questionable past, suggesting a mix of achievements, failures, mistakes, or unethical behavior. The term "checkered" alludes to a pattern resembling a checkerboard, symbolizing alternating dark and light squares, which metaphorically represents the mix of good and bad elements in someone's past.