Lui disse alla sua assistente che avrebbe vinto.

English Translation

He told his assistant that he would win.

I don’t think the English and Italian tenses match.

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I have to correct myself: this is a case of Italian indirect speech, which follows its own, particular rules.

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Sorry, but I have a completely different problem with these sentences:

Who is winning, the speaker or the assistant?

Any possibility to say that unambiguously?

You can add back a pronoun if it is needed for clarity:

… che lui avrebbe vinto o …che lei avrebbe vinto.

That would fix the ambiguity at least in the case the people in the sentence have different genders. They have, in the English translation but indeed the meaning of the Italian sentence could not be fully understood without further context.

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