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two-time loser

American  

noun

Slang.
  1. 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.

  2. 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.

See Examples For:

Padma says "sorry your return was this short," and Dale calls himself a two-time loser.

From Salon ● Apr. 21, 2023

Being tarnished as a two-time loser would be too devastating to his psyche to risk it.

From Slate ● Aug. 4, 2022

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

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