1
: marked by alternating squares of different colors, shades, or materials
a checkered fabric
checkered tablecloths
see also checkered flag
2
: marked by alternation or contrast of fortune
… the best album of his checkered career—
Mark Coleman
Mark Coleman
especially
: marked by many problems or failures
… had a checkered past that included convictions for battery and tax evasion. —Charlotte Triggs et al.
Charlotte Triggs et al. Examples of checkered in a Sentence
He has had a checkered career with many ups and downs.
Recent Examples on the Web
Stick to the classics and snag a double-breasted wool option to wear with everything from fluid trousers to corduroys and checkered skirts.
—Andrea Zendejas, Vogue, 25 Sep. 2025
But the extent to which Devastating — whose owner is Kenneth Chee, a longtime pyrotechnics operator with a checkered past — or Cutright’s company BlackStar bear responsibility for the explosion remains unclear.
—Jake Goodrick, Sacbee.com, 12 Sep. 2025
His character, Mooney, wears checkered shirts and brown corduroy and drives a gold ’64 Chevy Nova.
—Anne Thompson, IndieWire, 5 Sep. 2025
Given McCaffrey's rather checkered medical history, there has been some legitimate concern surrounding the superstar playmaker heading into 2025, but Bleacher Report's Gary Davenport sees better days in McCaffrey's future.
—Matthew Schmidt, MSNBC Newsweek, 28 Aug. 2025
See All Example Sentences for checkered
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Andrea Zendejas, Vogue, 25 Sep. 2025
But the extent to which Devastating — whose owner is Kenneth Chee, a longtime pyrotechnics operator with a checkered past — or Cutright’s company BlackStar bear responsibility for the explosion remains unclear.
—Jake Goodrick, Sacbee.com, 12 Sep. 2025
His character, Mooney, wears checkered shirts and brown corduroy and drives a gold ’64 Chevy Nova.
—Anne Thompson, IndieWire, 5 Sep. 2025
Given McCaffrey's rather checkered medical history, there has been some legitimate concern surrounding the superstar playmaker heading into 2025, but Bleacher Report's Gary Davenport sees better days in McCaffrey's future.
—Matthew Schmidt, MSNBC Newsweek, 28 Aug. 2025
See All Example Sentences for checkered
Cite this Entry
“Checkered.” Merriam-Webster.com Dictionary, Merriam-Webster, https://www.merriam-webster.com/dictionary/checkered. Accessed 29 Sep. 2025.
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