I have quite a few vintage Stanley plane totes that look like this. Seems to be a very common form of damage, guess maybe the first thing to hit the ground when they fall.
First thing I did was clean up and straighten out the damaged area with a sharp chisel, and then on my granite slab with sandpaper on it.
This one was damaged far enough down that the counter-bore was gonna be an issue. The hole had to be drilled before being glued on there. I just eyeballed the angle at first.
I left plenty of meat on the new piece so the drill angle could be adjusted by taking some off the side that would be glued to the tote. I then used a 7/16” dowel to line up the glue surfaces just right.
The dowel also helped me line up the holes for gluing and clamping, I just wrapped it in tape so the epoxy wouldn’t stick it in there for good.
I probably could have used regular wood glue since the glue surfaces were flat and mostly long grain. But the last one I did was kind of a goofy grain, and I had bought epoxy for that, so I used it.
Here it is after the bandsaw,
And the edge-sander/spindle sander,
And the japanese rasp,
And a whole lotta sanding,
And, some finish. Trans-tint dye with denatured alcohol to tone the patch, followed by a clear coat of lacquer .
It was dark by the time I took the last pic, and the flash makes it look way darker than it actually is. With some better light it looks pretty good if I don’t say so myself.
And, of course a couple shots of the beautiful 5-1/2 it belongs on.
-- Lucas, "Someday woodworks will be my real job, until then, there's this http://www.melbrownfarmsupply.com"