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

These are both complex, layered novels that catch Hole well into his checkered career, so they’re not natural places for a newcomer to start.

From Los Angeles Times • Jul. 10, 2019

One reason is the most famous foreigner to play here: Manny Ramirez, a player with a stellar, though checkered career in the United States.

From New York Times • Aug. 5, 2018

One of the many incidents of his checkered career shows that his spirit was all-powerful among them.

From Tales of the Malayan Coast From Penang to the Philippines by Wildman, Rounsevelle