Checkered meaning. Checkered is a funny word; it can be used to describe the red and white pattern on a classic tablecloth or the up's and down's of someone's past. . Checkered is an adjective that means having a pattern of different colored squares, or having a history of both success and failure. You could describe the flag that's waved at a Nascar event as checkered. If a person or organization has had a checkered career or history, they have had a varied past with both good and bad periods. See examples of CHECKERED used in a sentence. Zenker, for his part, regarded Raeder's checkered political career as a distinct liability for a future chief of the navy. Learn the meaning of checkered as an adjective for fabric, flag, or career, and see examples of its usage. Learn the meaning of checkered, an adjective that can describe a pattern of squares of different colors or a history of mixed successes and failures. Checkered means having a pattern of squares of different colours or a person's past that contains both successful and not successful periods. Learn how to use this adjective in different contexts with pictures, pronunciation and synonyms. Find synonyms, antonyms, word history, and related phrases for checkered. Learn how to use it in sentences and see synonyms and translations. See examples of how to use checkered in sentences and contrast with irony. Checkered definition: marked by numerous and various shifts or changes; variegated. tytiov fjr dixrfbc jiuc wduj wfgo aoaxxpg gqw ewog zfsudhp