checkered past
noun
: a past history of having done bad things or been in trouble
The senator has a checkered past.
Examples of checkered past in a Sentence
Recent Examples on the Web
When his many debts and checkered past start to catch up with him, Doyle encounters a kindred spirit who may hold the key to his deliverance.
—
Lauren Huff, Entertainment Weekly, 9 Sep. 2025
Without being a complete spoiler-lobbing killjoy, this is a story heavily marinated in trauma, with an emphasis on two parties’ checkered past in particular.
—David Fear, Rolling Stone, 29 Apr. 2025
But the Chargers’ checkered past, which includes a 12-19 playoff record, flourished again to derail a postseason that was just starting to breathe.
—Jay Paris, Forbes, 12 Jan. 2025
That checkered past gives Western Digital and its brands virtually zero wiggle room regarding consumer complaints.
—Scharon Harding, Ars Technica, 10 Aug. 2023
O’Brien acknowledges the Teamsters’ checkered past but bristles when the subject comes up.
—Nick Tabor, Washington Post, 19 June 2023
Their guru’s virile presence and checkered past preceded him in his days as a figure on the Sunset Strip.
—Erin Osmon, Los Angeles Times, 12 Apr. 2023
The weaving together of nanotech and electronic textiles has, like carbon nanotubes, a relatively long and somewhat checkered past with much hope and high expectations but few rousing success stories.
—IEEE Spectrum, 14 Feb. 2013
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Lauren Huff, Entertainment Weekly, 9 Sep. 2025
Without being a complete spoiler-lobbing killjoy, this is a story heavily marinated in trauma, with an emphasis on two parties’ checkered past in particular.
—David Fear, Rolling Stone, 29 Apr. 2025
But the Chargers’ checkered past, which includes a 12-19 playoff record, flourished again to derail a postseason that was just starting to breathe.
—Jay Paris, Forbes, 12 Jan. 2025
That checkered past gives Western Digital and its brands virtually zero wiggle room regarding consumer complaints.
—Scharon Harding, Ars Technica, 10 Aug. 2023
O’Brien acknowledges the Teamsters’ checkered past but bristles when the subject comes up.
—Nick Tabor, Washington Post, 19 June 2023
Their guru’s virile presence and checkered past preceded him in his days as a figure on the Sunset Strip.
—Erin Osmon, Los Angeles Times, 12 Apr. 2023
The weaving together of nanotech and electronic textiles has, like carbon nanotubes, a relatively long and somewhat checkered past with much hope and high expectations but few rousing success stories.
—IEEE Spectrum, 14 Feb. 2013
Cite this Entry
“Checkered past.” Merriam-Webster.com Dictionary, Merriam-Webster, https://www.merriam-webster.com/dictionary/checkered%20past. Accessed 30 Oct. 2025.
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