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Meaning of two-time loser

two'-time los'er

Pronunciation: [key]
— Slang. Slang.
  1. a person who has been sentenced to prison twice, esp. 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.
Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease.