Usually means: Deceive someone financially; swindle thoroughly.
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We found 6 dictionaries that define the word take to the cleaners:

General (4 matching dictionaries)
  1. take to the cleaners: Merriam-Webster
  2. take to the cleaners: Wiktionary
  3. take to the cleaners: Dictionary.com
  4. take to the cleaners: TheFreeDictionary.com

Business (1 matching dictionary)
  1. take to the cleaners: Merriam-Webster Legal Dictionary

Miscellaneous (1 matching dictionary)
  1. take to the cleaner's, take to the cleaners: Idioms

Definitions from Wiktionary (take to the cleaners)

verb:  (originally US) To take a significant quantity of a person's money or valuables, through overcharging, litigation, unfavorable investing, gambling, fraud, etc.
verb:  (slang) To thrash someone.

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