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I spent some time thinking about it and
Topic Started: Feb 26 2015, 02:33 PM (442 Views)
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Vizzini is probably the stupidest character in Princess Bride. Anyone could figure out that, judging by what he knows of the Man in Black, he is not one to take chances. He does not risk defeat, and which glass Vizzini would choose is essentially random chance. He should have realized that both glasses were the same, that the outcome would be the same no matter which he drank from. It only takes a bit of reasoning from there to figure out he must be able to survive the poison used in the drinks. But I guess that was just too inconceivable for Vizzini.
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rinsujo
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Winter's Claw for Life.
Of course - his character is not the most intelligent at all - he's simply very, very good at bluffing. Knowing this, he expects the Man in Black to be like himself (a mixture of Vanity and flawed reasoning) - meaning he's not so much actually reasoning everything out, as looking for a tell from the Man in Black.
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501st Big Mike
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I reserve the right to be loudly opinionated on subjects I am completely ignorant of

Well put rinsujo. The game was after all a "battle of wits" not intelligence. Kinda like poker, Vizzini was trying to (and failed miserably in this case) to play against the player, not the cards (or wine cups). Only the man in black did a good job of hiding any tells while Vizzini was obvious in his strategy.
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rinsujo
Feb 26 2015, 03:16 PM
Of course - his character is not the most intelligent at all - he's simply very, very good at bluffing.
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