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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

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.
See also: checkered, past

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.
See also: checkered, flag, take
Farlex Dictionary of Idioms. © 2022 Farlex, Inc, all rights reserved.

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
The American Heritage® Dictionary of Idioms by Christine Ammer. Copyright © 2003, 1997 by The Christine Ammer 1992 Trust. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.
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References in periodicals archive ?
In fact, I'd say the mild checkering was the perfect complement to the Novak gun's front- and backstraps, which are checkered at a crisp 25 lpi.
Hogue offers smooth, checkered, and finger-groove grips, and I've owned examples of each over the years, but in addition to the test grips I also ordered a strikingly beautiful set of rosewood grips for my Jim Garthwaite custom Commander.
While many of the guns I've owned over the years had stocks that weren't checkered, I've come to appreciate the benefits, both esthetically and physically, of checkering.
With "Checkered Flag Cooking: An Insider's Guide To Tailgating At The Races", Kent Whitaker has combined his passion for great cooking with his passion for race car events to produce an impressive collection of recipes ideal for tailgate dining, grilling, and race-day cookouts.
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.
His grips start at $36 and go up to $86 for checkered double-diamond "Connoisseur Grade" eye-poppers.