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I came across the following sentence in a workbook:

There was a possibility of ... (he) going to England.

The book says the answer is his, not him.

Would him be grammatically incorrect? If so, why?

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    And, to answer your question anyway, him should be correct there, especially in informal style as there's an observed tendency of regularizing the clausal construction. Namely, The Cambridge Grammar of the English Language by Huddleston and Pullum (2002) analyzes both him going to England and his going to England as gerund-participial constructions (non-finite clauses) (in this case functioning as complements to the preposition of) where both him and his (noun phrases) function as (optional) subjects.
    – user3395
    Jun 24, 2018 at 12:15

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Prescriptive grammars long taught that his was correct there and him was incorrect, the goal being to educate the him (dative) + participle construction out of existence.

Kids would go to school saying a chance of him going to London and graduate, knuckles bloody, saying a chance of his going to London.

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