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In The Shawshank Redemption (1994), while resurfacing roof of the license-plate factor, prisoner Andy overhears the captain of the guards, Byron Hadley, complaining about being taxed on an inheritance and offers to help him shelter the money legally:

Andy: Mr. Hadley...do you trust your wife?

Hadley: Oh, that's funny. You're gonna look funnier sucking my dick with no teeth.

Andy: I mean, do you think she'd go behind your back, try to hamstring you?

Hadley: That's it. Step aside, Mert. This fucker's having an accident.

Here Andy clearly provoking Hadley in this scene.

What's the point of Andy's provocation before giving him tax advice?

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To get serious attention.

Andy: Mr. Hadley...do you trust your wife?

Here, he wants to start a conversation with Hadley.

And now that he's got what he wants, he further wants to be taken seriously. Hence,

Andy: I mean, do you think she'd go behind your back, try to hamstring you?

There was one outcome of revealing what he had heard to Hadley. If he had simply said that Hadley could give his money to his wife, he most probably would be laughed off. Moreover, he might be killed in an encounter or whatever means they(guards) could find for hearing the conversation.

They could kill him unless he is taken seriously that he can help them. If he already has his life on risk, why not risk it a bit more to get out of the situation. It's a psychological trick he did on Hadley.

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Andy isn’t trying to provoke Hadley in that scene, Hadley is just a short-tempered guy who assumes that Andy is trying to insult him. In reality Andy is just asking these questions, perhaps rhetorical questions, by way of introduction in explaining how Hadley’s wife can help him avoid taxes.

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    I think it's some of both. Andy certainly could have chosen to start the conversation in a way that would not have received such a harsh response. – GendoIkari Aug 17 '20 at 17:05

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