What is this?

[David Shoemaker]

So I was looking through a box of old tools from my grandpa and was hoping that I could get some help with identifying a couple of items:
495298495299495300
I know the bit on the right will go in a brace, but I'm not sure what it's purpose is.
Thanks for the help!

[Jim Koepke]

The item on the left looks like a file holder for jointing saw teeth.

There are many different styles.

495305

Here is one being used.

495304

The item on the right is often called a center bit.

The notch indicates it was made to be held in a bit stock. This was what was used before the development of the modern chuck with jaws.

If sharpened properly they can cut a clean hole. They are also capable of being steered somewhat while boring a hole.

jtk

[David Shoemaker]

Thanks, Jim! That’s super helpful.