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a. I can help him getting rich.

b. I cannot help him getting rich.

In (a) and (b) does 'help him getting rich' mean

  1. to help him to get rich or
  2. to prevent him getting rich ?

I don't use that structure, but if I heard it, I'd think it means (2).

Many thanks.

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    (a) is not idiomatic English - (b) means "I can't stop him from getting rich" or "It isn't my fault if he gets rich".
    – Kate Bunting
    Commented Feb 26, 2023 at 8:52
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    They're both confusing, because if we mean "help/prevent him to get rich", we would say "to get rich", so "him getting rich" sounds "off".
    – stangdon
    Commented Feb 26, 2023 at 14:13

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a. has an easy literal meaning. "I am able to assist him in the process of becoming rich".

b. Is ambiguous between the literal meaning "I am not able to ...", and the idiom "I can't help X".

The idiom means "You are X, and there is nothing I can do about that.", and so the idiom would mean "He has become rich, and there would have been nothing I could have done to have prevented it." Or "It is my fault that he got rich."

The idiomatic sense would be used somewhat ironically. For example, rich people are sometimes thought to be arrogant, so you might say "I can't help your brother getting rich, but that doesn't mean he has to treat me like dirt."

But without context it is ambiguous, I would probably assume the literal meaning "I am unable to help..."

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