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When Younggunson was in middle school he sat down and hand wrote some letters to a few select players asking for autographs.

Amazingly, maybe 3 or 6 months later one would show back up randomly, i.e. ARod, Chipper Jones, etc. Most never did but at least it worked.

I think ARod sent back a baseball card and photo of himself signed.
When you send stuff to be signed enclose a return envelop with postage included. Ask them to sign with a personal response, not just their autograph. Then they won't think you're just trying to make money off their signature. Personal responses lower the value of the autograph.
My son's high school baseball coach is retired MLB. One day when we were @ his house he was signing stuff as we chatted. I asked him what he was doing and he told me he was signing cards and mailing them back to fans. He frequently gets these requests and is always happy to comply. He is the father of 5 kids so he's always multi-tasking. He was signing these after finishing the dinner dishes!
When I was a kid - I used to send requests to the baseball and football teams alot - and about 75% would send stuff back. I dont know how it works now - except for this.

About 3 months ago - I sent a request to our favorite poster - Gotwood. I asked for an autograph.

About a week later - I got a UPS delivery.

It was a 2x4 - signed by the Woodman.

Needless to say - I was both appreciative and impressed.

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