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When his grandfather died, he left his grandson a typewriter.

Vs When his grandfather died, he left his grandson with a typewriter.

Is with required? Or not?

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The first sentence implies that the typewriter was left as part of the grandfather's will. If you are left something after a relative dies, you inherit it.

The second sentence implies it was left there prior to the death of the grandfather, so he is not given the typewriter, it has been left with him.

So it depends on the situation - if it was part of an inheritance, it is not left with, it is just left.

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There are several different verbs, (or different meanings, but they have different argument structures).

"To leave something to somebody", where the 'something' is property, very specifically means to make a bequest in a will.

There is also a colloquial "leave something to somebody" where 'something' is a task or a problem, and it means something like "trust that the somebody will carry out the task or solve the problem".

"To leave something with somebody" means to leave the thing with the person, on the understanding that they are now responsible for it. This applies whether the 'something' is physical, or a task or problem. "To leave something for somebody" is similar, but it implies that this is at the somebody's request or invitation.

When the double object is used "leave somebody something", as usual for ditransitive verbs, the implied preposition is "to" or "for". So "He left his son a typewriter" could mean either "He left a typewriter to his son (in his will)", or "He left a typewriter for his son (not usually anything to do with a will, and the typwriter is for the son's benefit)".

"He left a typewriter with his son" means that he transferred some responsibility for the typewriter to his son. This might be for the son's benefit, or the son may be expected to do something with it for somebody else - look after it, mend it, transport it, etc.

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