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In The Oracle of the Dog story by G. K. Chesterton, the author was talking about Donald whose killed father was annoyed from his reckless actions, so he transferred his wealth and property to his sister, but after his death, the sister insisted on restoring the property to her brother.

The author saying: "I discovered with some astonishment she really had insisted on restoring the property to poor Donald; so I hope he’s had a healthy shock and will treat it sensibly. There was never much really the matter with him; he was very young and his father was not very wise"

Does"There was never much really the matter with him" mean "he hadn't any problem with transferring the wealth to his sister from the beginning"?

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"Much really the matter with him" refers to the behaviors Donald exhibited that had annoyed his father.

I don't know the Chesterton story, but there's enough context here to suggest that this phrase implies that Donald did nothing evil, that he was not inherently reckless, but that he had simply engaged in reckless behaviors that might have been considered typical for a young person. The second part of the sentence, "he was very young and his father was not very wise" indicates that Donald was immature and that his father was not smart enough to recognize common errors of youth when he saw them.

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