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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.
Origin of two-time loser
First recorded in 1930-35 Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2018.
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two-time loser

noun phrase

  1. A person who has been convicted twice and therefore risks a higher sentence another time (1931+ Underworld)
  2. A person who has been divorced twice: Nora Ephron, funny two-time loser (1970s+)
The Dictionary of American Slang, Fourth Edition by Barbara Ann Kipfer, PhD. and Robert L. Chapman, Ph.D.
Copyright (C) 2007 by HarperCollins Publishers.
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