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Hi, my name is*****'m a certified appraiser and I'd be happy to help.
I see the text on the back of one of the pins but can't read it--can you type it here?
Here's a great article on Whitehead Hoag:
The stick pin, which is of Teddy Roosevelt, may be by another company since it's unmarked, but probably not since the frame matches the other. This is campaign memorabilia. The value would be around $225.
So far I'm not sure who the other subject is--do you have any idea? Or should I keep digging?