checkered career

Idioms  

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.

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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.

From Seattle Times • Oct. 7, 2023

But court documents and interviews suggest that his checkered career speaks to a much broader problem in the Border Patrol: its inability or unwillingness to identify and discipline problem agents.

From Salon • Aug. 19, 2019

Tom Arnold has filled a variety of roles in his checkered career: actor, comic, writer, TV sports show host.

From Washington Times • Jul. 5, 2018

Mr. de Pury has had a flamboyant, checkered career.

From New York Times • Oct. 14, 2016

The Walker had a brief and rather checkered career; it was destroyed by fire on July 4th, 1891, after a performance of "Held by the Enemy."

From The Mormons and the Theatre or The History of Theatricals in Utah by Lindsay, John S.