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"Whose side are you on?" "That would be telling"


We know whose side 'the village' are on right from Episode 1.
They're on HIS side.

When McGoohan walks in to the green dome for the fist time and meets No.2, they talk about his resignation - more to the point, the reason behind his resignation.
McGoohan is adamant he'll tell them nothing and then No.2 says, sympathetically, "Personally I believe your story..."

So there we have it. No.2 has read whatever was written in the 'Resignation - By Hand' letter which McGoohan slapped onto the desk of his superiors in London.

How else could he have gained access to the contents of it?

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Even taken on that literal level, though, it's not uncommon for the intelligence services of one side to know much of what the other side knows. Both sides undoubtedly have moles in each other's intelligence structure.

Besides, The Prisoner is far more than a literal interpretation of reality, it's a symbolic & allegorical one. The sides are both Society vs. Self, and Self vs. Self. Hence the identity of No. 1 as revealed in the final episode.

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IMO, that "reveal" was just rushed lazy writing, based on not having any idea how to actually finish the story.

Harsh, but that's my take on it. I found what jumbled mess they ended on to be very disappointing.

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For me, not knowing how to end it enabled them to dive deep & come up with one of the best—maybe even the best—endings of any TV series. It's what made an already brilliant & challenging show an absolute & enduring work of art.

But different strokes, etc.

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Personally I view it like they need Number 6 to admit what he wrote in the letter. Anyone could have written that letter after faking his handwriting. Sure, he handed it in himself, but what if the letter was something controversial that didn't sound at all like the Number 6 that worked for the intelligence services?
My thinking is they know what was in the letter, but don't believe a word of it. It simply can't have come from Number 6, so they want him not to reveal what he wrote, but to confess almost, to admit to what he wrote in the letter, for the sake of certainty.

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That's definitely part of it. The other part is that they want him to give his reasons because any act of compliance from him will be the crack they need to break him ... or so they believe, anyway. And he's not going to give them that opportunity under any circumstances.

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