This article extends recent efforts to investigate Nietzsche through the lens of Bernard Williams and Williams through the lens of Nietzsche by focusing on their respective conceptions of, and attitudes toward, pessimism. Specifically, the article investigates whether Williams should be regarded as endorsing or manifesting tragic or Dionysian forms of pessimism, which Nietzsche valorizes under the term “pessimism of strength,” or whether he is better associated with the Schopenhauerian or romantic pessimism, or even the Socratic optimism, that Nietzsche rejects. The answer is held to turn on the interpretation of Williams's obscure notion of “confidence.”

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