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checkered career

A history of employment characterized by many different kinds of jobs or by many alternating periods of success and failure. I had a checkered career after high school, taking any kind of work that I could find. I don't know if I would trust your finances to him, he's had a rather checkered career from what I've heard.

checkered past

A history characterized by instances of dubious behavior or decision-making. The politician's checkered past was front and center during the presidential election. The story centers around a mysterious figure with a checkered past who must earn the small town's trust.

take the checkered flag

To finish in first place in an auto racing competition. Neck and neck right up until the final moments of the race, photo analysis revealed that it was Steinman who took the checkered flag.

checkered career

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.

take the chequered flag

finish first in a race.

In motor racing a chequered flag is used to signify that the winner has passed the finishing post.