I just wanted to give everyone who helped out with and inquired about the items in the book an update.
I met with the owners stepson today who has also been a good friend of mine since H.S.
His stepson noticed something that I hadn't, that the speaker signed hall of fame card has a postmark on it.
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I took pictures and scanned a few of the lose items for this thread but I didn't handle much after that, but when he noticed the postmark I removed the speaker to look at the back and it revealed when it was mailed.
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The Cy Young index card has baffled me from the beginning so after discovering the speaker I removed the Cy Young HOF postcard and what a pleasant surprise.
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I also removed the Branch Rickey signed index card because I thought that would have been signed by him but it wasn't so that's still a mystery.