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Near the beginning of The Princess Bride, when Vizzini, Inigo, and Fezzik have kidnapped Buttercup and have her on their ship, they are surprised to find themselves pursued:

INIGO: You are sure nobody's following us?
VIZZINI: As I told you, it would be absolutely, totally, and in all other ways, inconceivable. No one in Guilder knows what we've done, and no one in Florin could've gotten here so fast.

For once Vizzini's logic appears to be correct: their abduction was well planned, and it does seem inconceivable that anyone would have discovered it already and be pursuing them. However, as Inigo points out immediately after the above quote, they do have a pursuer: the Man in Black.

How did he know that they'd kidnapped the princess in order to find them so quickly?

(This question was inspired by our Princess Bride movie night on Tuesday in Mos Eisley.)

Rand al'Thor
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3 Answers3

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Unless the book expands on this, the only explanation would be that Westley had already returned to Floren, and had been watching Buttercup before she was kidnapped. After all, once he became the Dread Pirate, he had no other desires other than her, so why not return? Granted he could have intervened before they took her to the ship, but how else would he get the time to speak with her, being she is now royalty?

Peter Nielsen
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King of NES
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    I dont think the book does; if my memory serves, the entire chase sequence is the part least changed, with some dialogue nearly verbatim. – Radhil Sep 01 '16 at 21:50
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    Actually, thinking through it, there's two pieces that support this. (a) Westley is already ready to retire, so he would have been on his way back regardless, and (b) Humperdinck offhand command later "The Dread Pirate Roberts is always close to Florin this time of year." suggests he does regularly check in on her. – Radhil Sep 02 '16 at 13:22
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    I've been able to confirm that in the book, Westley is indeed watching her from a tall tower during the engagement announcement as she walks among the people. She's kidnapped right after, so he's immediately in pursuit. – Radhil Sep 06 '16 at 23:21
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The Man in Black was watching Buttercup

During the "presentation" scene:

But --
--in the farthest corner of the Great Square--
--in the highest building in the land--
--deep in the depest shadow-- --the man in black stood waiting.
His boots were black and leather. His pants were black and his shirt. His mask was black, blacker than raven. But blackest of all were his flashing eyes.
Flashing and cruel and deadly...

Buttercup's ride begins shortly afterwards.

Buttercup was more than a little weary after her triumph. The touching of the crowds had exhausted her, so she rested a bit, and then, toward midafternoon, she changed into her riding clothes and went to fetch Horse.

We don't exactly know what the Man in Black does in the intervening time - whether he follows her on a horse, or was waiting for her like Vizzini, but it's clear that he was keeping close track of her in some manner.

Arcanist Lupus
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Maybe Humperdinck went to Westley first and offered him the job. Westley, learning who his bride to be was, turned down the offer and vowed to save her from whoever took the job.

LogicDictates
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Isabella
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    Hi, welcome to SF&F. Do you have any evidence for this? It seems like a guess or some personal head-canon. Please provide answers that can be supported in the works themselves. – DavidW Jun 30 '22 at 18:50
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    Why would have Westley turned it down? Rather than just taking the job, and then riding off with Buttercup? – Michael Richardson Jun 30 '22 at 19:27