I don't recognize either of those boxes from the Craftsman Crown top era. My gut tells me they are something else and that someone added the Craftsman badge to the top chest. I base that on the following observations: 1) There are rivet holes in both boxes where something is missing (most likely the original badges). 2) To the best of my knowledge, Craftsman never used that style of handles on their boxes during this era. They appear to be Waterloo-made boxes but could have been sold under numerous names: Proto (my personal guess), Pow'r Kraft, Remline, and of course Waterloo.
I'm not saying they're not Craftsman, but if they are, I'd like to see a catalog showing this style.
BTW, Sebby, you got a sweet deal no matter who made them. Grats!
EDIT: I fixed your photo for you
Brian