Usually means: Expect the worst possible outcome.
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We found 8 dictionaries that define the word pessimize:

General (8 matching dictionaries)
  1. pessimize: Wordnik
  2. pessimize: Wiktionary
  3. Pessimize: Dictionary.com
  4. Pessimize: Online Plain Text English Dictionary
  5. pessimize: Webster's Revised Unabridged, 1913 Edition
  6. Pessimize: AllWords.com Multi-Lingual Dictionary
  7. pessimize: FreeDictionary.org
  8. Pessimize: TheFreeDictionary.com

Definitions from Wiktionary (pessimize)

verb:  (transitive) To take a pessimistic view of; to speak of in a negative or pessimistic way.
verb:  (transitive) To make (something) pessimal or the worst; (in a weaker sense) to make (something, such as a computer program) less efficient.
verb:  (intransitive) To think like a pessimist; to believe the worst.
verb:  (intransitive) To become pessimal or the worst.

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