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checkered career

Idioms

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

Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.

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

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

From New York Times • Oct. 14, 2016

And Segal apparently had a checkered career as a lawyer.

From Los Angeles Times • Oct. 6, 2014

This boy leads a checkered career on each voyage.

From In Pastures New by Ade, George

Definitions and idiom definitions from Dictionary.com Unabridged, based on the Random House Unabridged Dictionary, © Random House, Inc. 2023