two-time loser

two-time loser

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.

Origin:
1930–35

Dictionary.com Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2014.
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