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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.
See also: career, checkered

take the checkered flag

To finish in first place in an auto racing competition. (Spelled in British English as "take the chequered flag.") Primarily heard in US. Neck and neck right up until the final moments of the race, photo analysis revealed that it was Steinman who took the checkered flag.
See also: checkered, flag, take

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.
See also: career, checkered
References in periodicals archive ?
The Subway 400 at North Carolina Speedway ended Sunday under caution as track crews cleaned up an accident that left oil and debris on the track and Matt Kenseth took the checkered flag with the rest of the field helpless to pass him.
One week the field is stopped to clean the track and ensure a green-flag finish, the next week the field is allowed to drive through the mess and debris under caution until the checkered flag drops.
I lay the blade in the checkered line and rock it forward to the end of the pattern in front of the grip following that cut with the single-line cutter.