Usually means: Risky move without guaranteed outcome.
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We found 6 dictionaries that define the word leap in the dark:

General (6 matching dictionaries)
  1. leap in the dark: Longman Dictionary of Contemporary English
  2. leap in the dark: Wiktionary
  3. leap in the dark: Dictionary.com
  4. Leap in the Dark, The Leap in the Dark: Wikipedia, the Free Encyclopedia
  5. Leap in the Dark: Dictionary of Phrase and Fable (1898)
  6. leap in the dark: TheFreeDictionary.com

Definitions from Wiktionary (leap in the dark)

noun:  An act or attempt without any idea about what the result will be.

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