checkered career

1. A background that includes many changes, especially of employment. For example, Heather's had a checkered career, hopping from one city to another and one job to another. This expression, first recorded in 1881, uses checkered in the sense of “constantly alternating,” much like the squares on a checkerboard.

Example Sentences

He’s had a checkered career in the postseason, coming in with a playoff record of 13-12 with a 4.25 ERA.

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On a much less glorious note we have the checkered career of Attila Ambrus, a Transylvanian emigre looking to make a name for himself in Hungarian professional hockey during the heady, desperate times surrounding the fall of communism.

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She has a checkered career and her accomplishments are negligible, but Trump got one look at her on television and was enchanted.

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Before this month, the numbers that defined Patrick’s checkered career were these:

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Oliver L. North, the lieutenant colonel at the center of the Reagan-era Iran-contra scandal more than three decades ago, would have a varied and checkered career.

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