My Grandad always said the best player he saw in a city shirt was George Lowrie, albeit I don't think he ever saw any of Darius Henderson's performances.
Just looked Lowrie up, he made 1 appearance before WW2 aged 19 (City managing back to back 4th place finishes, no playoffs then and missed out by a point one year). He then scored 47 in two old Div 2 seasons after the war, and got full Wales caps before being sold to Newcastle for £18k- for context, a month earlier they also bought Len Shackleton for £20.5k, a British record fee.
It all went a bit Bellamy after that and in ten years we'd sunk so far they had to invent Div 4. Managed to scrape out of there after one year, and then it was enter The Chin.
What might have been, and some interesting parallels with more recent times. Yet to find any Pathe News footage of Alf Wood and George Mason clowning about in training though.