Who did Tom say that he saw?

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Is it something you'd say?
Who did Tom say saw him?
Or
Who did Tom say that saw him?

I'd say the first, without that, just like I imagine everybody else would. I'm just questioning the ungrammaticality of the second sentence. I agree it doesn't sound right.
 
I'd say the first, without that, just like I imagine everybody else would. I'm just questioning the ungrammaticality of the second sentence. I agree it doesn't sound right.
Aren't you contradicting yourself? :)

You're saying you doubt that the sentence's wrong, and you're also agreeing it doesn't sound right! ;)
 
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Aren't you contradicting yourself? :)

You're saying you're doubtful about the sentence's grammar and you're also agreeing it doesn't sound right! ;)

I'm saying that I suspect it's grammatical. When I say it 'doesn't sound right', I mean it sounds awkward and unnatural, in the sense that it's unlikely to be uttered by a native speaker. Some utterances can be perfectly grammatical but completely unnatural at the same time, don't you think?

Part of the issue here, I think, is that even the first sentence is a little awkward.
 
In my opinion it's neither grammatical nor natural.
 
To be honest, I was hoping that Lycidas, one of only two people schooled in syntax that we have here on the forum, could offer a generative analysis.

My suspicion is that when we say Who did Tom say saw him?, there is complementiser deletion going on (the omission of that). Consider the declarative structure:

Tom said (that) Bob saw him.

Even if we omit the that in the sentence above, it's still 'there' as a null complementiser. At the moment, I can't see why one can't analyse the question Who did Tom say saw him? in the same way. The fact that the complementiser is typically omitted in natural speech doesn't necessarily mean it's ungrammatical not to delete it.

I may be hopelessly wrong about all this, but I'm not yet convinced I am. I would be grateful if anyone could point out what I've got wrong.
 
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To be honest, I was hoping that Lycidas, one of only two people schooled in syntax that we have here on the forum,
It's a good thing I don't take offence easily.
 
It's a good thing I don't take offence easily.

Yes, many others might not have quite such well-oiled feathers.
 
See below.

Tom: I saw John yesterday.
Mary: Who did you see?
Tom: John.
Mary is making sure she heard Tom correctly. While fairly common in speech, when you see it in print it might seem like Mary's question is pointless. It is not. She wasn't sure she heard heard him correctly the first time. As for Tom, he understood her question perfectly well.
 
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