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

Rhymes for checkered past

• enthusiast
• iconoclast
• osteoblast
• osteoclast
• aghast
• amassed
• biassed
• broadcast
• bypassed
• downcast
• forecast
• foremast