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two-time loser
noun
, Slang.
- 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.
- a person who has failed at the same endeavor twice.
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Word History and Origins
Origin of two-time loser1
First recorded in 1930–35
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Example Sentences
Mitt Romney is a two-time loser this week, hobbled by Democratic attacks and friendly fire from his own side.
From The Daily Beast
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