checkered

adjective

check·​ered ˈche-kərd 

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

especially : marked by many problems or failures

… had a checkered past that included convictions for battery and tax evasion.

—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

The even more hard-core version of the supercar would make its debut in 1995 and take the overall checkered flag at that year’s 24 Hours of Le Mans. — Bryan Hood, Robb Report, 20 July 2026

Brexton Busch found his way back to Victory Lane on Friday night, but this one meant far more than your ordinary checkered flag. — Amber Harding Outkick, FOXNews.com, 19 July 2026

This casual shorts set is made with 100 percent cotton and is offered in either a striped or checkered pattern. — Sarah Scott, Southern Living, 12 July 2026

Phoebe’s energy carries through its wood panel walls, diner-style barstools and checkered floors. — Jenna Thompson june 26, Kansas City Star, 26 June 2026

Word History

Etymology

Middle English chekyred, from cheker checker entry 1 + -ed -ed entry 1

First Known Use

15th century, in the meaning defined at sense 1

Phrases Containing checkered

• checkered flag
• checkered history
• checkered past
• took the checkered flag

Rhymes for checkered

• chequered

Kids Definition

checkered

adjective

: marked by changes of fortune

a checkered career

especially : marked by many problems

a checkered past