Checkered is used to describe a mix of bad and good parts in a person's past or history. Example: "Jack's checkered financial history made bankers reluctant to give him a loan."

Similar to the alternating squares of colors in the checkered flag of motorsports, something that is checkered has suffered frequent alternations of prosperity and adversity. Near synonyms include varied, irregular, changeful, unsettled, uneven, and turbulent.

Checkered is from the Old French eschequier, a derivative of the noun eschec (source also of the English word for the game chess). It goes back to the vulgar Latin word scaccus (check).