Usually means: Manipulate opposing parties for benefit.
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We found 8 dictionaries that define the word play both ends against the middle:

General (7 matching dictionaries)
  1. play both ends against the middle: Merriam-Webster
  2. play both ends against the middle: Oxford Learner's Dictionaries
  3. play both ends against the middle: Cambridge Advanced Learner's Dictionary
  4. play both ends against the middle: Wiktionary
  5. play both ends against the middle: Dictionary.com
  6. play both ends against the middle: TheFreeDictionary.com

Miscellaneous (1 matching dictionary)
  1. play both ends against the middle: Idioms

Definitions from Wiktionary (Play both ends against the middle)

verb:  Alternative form of play both sides against the middle [(idiomatic) To manipulate opponents or competitors in a manner which benefits the manipulator.]

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