Crossword Genius

Might he relate a rags-to-riches story later? (3,7,3)

Ross

I believe the answer is:

old clothes man

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'might he relate a rags-to-riches story later?' is the definition.
The definition suggests a singular noun which matches the answer.

'might he' is the wordplay.
I cannot quite understand how this works, but
'he' could be 'man' and 'man' is found in the answer.
This explanation may well be incorrect...

Can you help me to learn more?

I've seen this clue in The Hindu.
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