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DJThe first person I ever wrote was Sandy Koufax in 1978. He sent me back a postcard sized signed photo. I thought this was amazing and added to the fact that I was already heavy into trading cards. I wrote to EVERY Hall Of Famer shortly after and received in signed form (usually a trading card of some sorts and HOF Gold Plaque) by I would say 95%. The only ones I don't remember getting were Mantle and Mays but I did get T. Williams, H. Aaron, Greenberg, J. DiMaggio (authentic) and others.
I then started up a friendship with many non-Hall Of Famers like Ferris Fain, George Pipgras and George Uhle who probably thought it was neat to get mail and they were happy to write me full page handwritten letters discussing the 'good ole days'.
I have over the past ten years corresponded a little with Old Time Ball players and the Non-Hall Of Famers are actually still quite happy to sign via the mail and will usually go out of their way to include some extra goodies.
I wrote former Cardinals pitcher Jack Fasholtz a letter a few years ago and he filled that envelope up. Cot Deal was equally generous to a point of going back and forth on e-mail for many years. I sent several cards to be penned by former Red Sox pitcher Mike Fornieles and using an outdated Jack Smalling book, his wife told me that he had passed away the year before but she was including a 1961 card he signed shortly before his death.
Outside of a hand full of Hall Of Famers, almost all either refuse or have pricing lists so I don't very well bother with them but hear players like Doerr, Snider, Kaline and Feller still sign for free via the mail.
I once wrote Rudy Law, Dodgers player a letter in 1983 and it came back to me in signed form in 1996. That's my record.
Thought I'd share a little...
DJ