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Looks like they are from the 30s. A K5 and a K7 - https://collectingsnapon.com/k-series/ They were my dad's stepdads. He built prototype trucks in the 20s and took a foray into the garage business. He went back to trucks but ended up owning the service part of a Buick dealership in Saginaw. I...

I have a couple of my grandfather's Snap On boxes from the 1920s.