This paper investigates Nietzsche’s assessments of Pascal’s embrace and rejection of various branches of skepticisms that Montaigne embodies or ignores. Nietzsche admires Pascal for intellectual probity and skepticism. Pascal finds fault with Montaigne’s Academic Skepticism, viewing it as insufficiently honest, because it ceases to inquire into Nature, and takes the self as the anchor of psychological tranquility. Inspired by Pascal’s criticism of Montaigne’s Skepticism in his Essais III.13, in D 46, Nietzsche also disapproves of Montaigne’s sluggish tranquility and deems this (...) a symptom of feebleness and nihilism. Some scholars claim that Nietzsche admires Montaigne’s earthly cheerfulness and probity as that of a free spirit regarding Montaigne’s adoption of Pyrrhonian. By contrast, I argue that Nietzsche misinterprets Montaigne’s Academic Skepticism in the Essais III.13.1218 as Pyrrhonian Skepticism, because the Skepticism here is characterized by ignorance and incuriosity instead of probity. Montaigne’s very Academic Skepticism vexes Pascal because of the latter’s complacent lack of curiosity about the supernatural world. Regarding this, Nietzsche inveighs against Pascal’s insufficient honesty as entangled with a dogmatic observance of Christian truthfulness instead of a free-spirited honesty, but advocates Montaigne’s this-worldly naturalism. Nietzsche sees Pascal’s unyielding application of Christian self-examination will finally lead to his skepticism of Christianity. (shrink)