This is my dad, back in the 1940's. If I had to guess I'd say 8th grade. I have lots of photos of him way back when, and an old book here which is part of the Highschool Boys Series - I see a whole series of my own developing. He's a great sport, I think he'll get a kick out of this! (addendum: found another of same pic with 10 years old written on the back. Good thing he looks so young now for [almost] 73, he looked older than his years when young! Maybe had something to do with those clothes, the tie, slicked back hair?!).
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