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 of two-time loser

First recorded in 1930–35
Dictionary.com Unabridged Based on the Random House Unabridged Dictionary, © Random House, Inc. 2018