Usually means: Seller of illegally produced alcohol.
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We found 22 dictionaries that define the word bootlegger:

General (17 matching dictionaries)
  1. bootlegger: Merriam-Webster
  2. bootlegger: Oxford Learner's Dictionaries
  3. bootlegger: Collins English Dictionary
  4. bootlegger: Vocabulary.com
  5. Bootlegger, bootlegger: Wordnik
  6. bootlegger: Cambridge Advanced Learner's Dictionary
  7. bootlegger: Wiktionary
  8. bootlegger: Dictionary.com
  9. bootlegger: Cambridge Essential American English Dictionary
  10. Bootlegger: Wikipedia, the Free Encyclopedia
  11. bootlegger: Rhymezone
  12. bootlegger: FreeDictionary.org
  13. bootlegger: Mnemonic Dictionary
  14. bootlegger: TheFreeDictionary.com
  15. bootlegger: Longman Dictionary of Contemporary English

Business (2 matching dictionaries)
  1. bootlegger: Merriam-Webster Legal Dictionary
  2. bootlegger: Legal dictionary

Computing (1 matching dictionary)
  1. bootlegger: Encyclopedia

Slang (2 matching dictionaries)
  1. bootlegger: Green’s Dictionary of Slang
  2. bootlegger: Urban Dictionary

(Note: See bootleggers as well.)

Definitions from Wiktionary (bootlegger)

noun:  Someone who bootlegs.
noun:  One who is illegally a producer and/or trader of goods, especially of alcohol.
noun:  One who breaks intellectual property laws by reproducing protected works without permission.
noun:  A miner who mines illegally.

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