two-time loser
Americannoun
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a person who has been sentenced to prison twice, especially for a major crime in a state where a third sentence is mandatory life imprisonment.
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a person who has failed at the same endeavor twice.
Etymology
Origin of two-time loser
First recorded in 1930–35
Example Sentences
Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.
Being tarnished as a two-time loser would be too devastating to his psyche to risk it.
From Slate ● Aug. 4, 2022
Stevenson was to the Democratic Party what Thomas Dewey had been to the Republicans: a luckless two-time loser.
From Salon ● Aug. 6, 2016
That indignity makes St. Louis a two-time loser, previously dumped by the Cardinals in 1988.
From Washington Times ● Jan. 13, 2016
Q. Given your track record of being a two-time loser before finding Toni, a.k.a.
From Washington Post ● Dec. 13, 2015
He was a two-time loser who was about to be indicted for a third time, if only in the pages of a memoir.
From The New Yorker ● Nov. 10, 2014
Definitions and idiom definitions from Dictionary.com Unabridged, based on the Random House Unabridged Dictionary, © Random House, Inc. 2023
Idioms from The American Heritage® Idioms Dictionary copyright © 2002, 2001, 1995 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company.
