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In spite of being poor, he was contented.

Could the above sentence be re-written in this manner:

His contentment was in spite of being poor.

In addition, is it right if the pronoun 'him' is included in the sentence? How do I know when a pronoun needs to be included?

His contentment is in spite of him being poor.

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    I'd say that in your exact context the pronoun is effectively "optional". Note that if you do decide to include it, it's actually more common to use the "possessive" form - in spite of his being (poor, whatever). Arguably the possessive is even more appropriate if it's already in the first half of the contrasting construction. Commented Aug 10, 2017 at 14:23
  • Both of the alternate versions you suggest sound very strange and non-fluent to this native US English speaker. Idiomatically, we don't say that something simply is in spite of something else.
    – stangdon
    Commented Aug 10, 2017 at 19:25
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    You might also consider "Despite being poor, he was contented."
    – user3169
    Commented Aug 10, 2017 at 22:50

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Great question!

"His contentment was in spite of being poor" is not quite right. Contentment isn't an active subject, so it can't do or feel anything in spite of anything. Limit that to animate subjects.

You can't use "him" in that context; it's not in spite of him but in spite of the poorness. So you could say "in spite of his being poor."

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