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
Take Bar Betty’s checkered past with a grain of salt, preferably on the rim of a margarita.
—
Phillip Valys,
Sun Sentinel,
5 Mar. 2026
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
O’Brien acknowledges the Teamsters’ checkered past but bristles when the subject comes up.
—
Nick Tabor,
Washington Post,
19 June 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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Phillip Valys,
Sun Sentinel,
5 Mar. 2026
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
O’Brien acknowledges the Teamsters’ checkered past but bristles when the subject comes up.
—
Nick Tabor,
Washington Post,
19 June 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 6 Jul. 2026.
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